Moving from Chicago and Illinois
Moving from Chicago to Palm Beach County
Most Chicago buyers start in Palm Beach (if you love the Gold Coast), West Palm Beach (Streeterville and the West Loop), Palm Beach Gardens (Lake Forest) or Jupiter Island (Winnetka). Illinois taxes estates above $4 million and has one of the highest property tax rates in the country; Florida has no income, estate or inheritance tax. American flies nonstop to O’Hare.
Moving from Chicago and Illinois
Which Palm Beach County Towns Feel Most Like Chicago?
Cook County sends more people to Palm Beach County than any county outside the New York area, followed in Illinois by Lake and DuPage. Chicago buyers usually know exactly what they want because they already live it: a walkable lakefront, an old club, a tower with a view. Here is where to find each one, on the ocean.
For a Chicago buyer leaving the Gold Coast, start with Palm Beach; leaving Streeterville and the West Loop, West Palm Beach; leaving Lake Forest, Palm Beach Gardens; leaving Winnetka and Kenilworth, Jupiter Island. To weigh every town at once by water, clubs, downtowns, commute and live prices, see Where to Live in Palm Beach County: The Towns Compared.
| If you are leaving | Start with | Why it fits |
|---|---|---|
| The Gold Coast | Palm Beach | The Gold Coast's walkable blocks of vintage co-ops, a short walk from the lake and Oak Street, translate neatly to Palm Beach: postwar co-ops and quiet avenues on an island, with Worth Avenue for Oak Street and the Atlantic for Lake Michigan. |
| Streeterville and the West Loop | West Palm Beach | New buildings line Flagler Drive on the Intracoastal, and downtown is growing with new offices and restaurants. |
| Lake Forest | Palm Beach Gardens | Lake Forest's old clubs and big lots point straight to Palm Beach Gardens, where private golf clubs set the rhythm of the week and the homes sit inside the gate. |
| Winnetka and Kenilworth | Jupiter Island | The quiet, leafy streets and lakefront of Winnetka have their match on Jupiter Island: estate homes between the ocean and the Intracoastal, the Jupiter Island Club and no commercial strip. |
| Hinsdale and Naperville | Jupiter | Abacoa has its own downtown, and the beach is about fifteen minutes away. |
| Barrington Hills | Wellington | Barrington Hills' acreage and horse trails continue in Wellington, where barns, riding trails and the winter show-jumping and polo seasons are part of everyday life. |
| Lake Geneva weekends | Stuart | Lucie River, and a slower pace at the north end of the Treasure Coast. |
- No estate taxIllinois taxes estates above $4,000,000; Florida does not.
- Lower property taxesIllinois's median rate is 1.88%; Palm Beach County's is 0.82%.
- No state income taxIllinois is a flat 4.95%; Florida has none.
- Winter, solvedAbout 66 degrees in January, on average.
- O'Hare nonstopAmerican flies it year round.
Find Your Match: 7 Places to Start
you’ll love Palm Beach
02If you loveStreeterville and West Loopyou’ll love West Palm Beach
03If you loveLake Forestyou’ll love Palm Beach Gardens
04If you loveWinnetka and Kenilworthyou’ll love Jupiter Island and Hobe Sound
05If you loveHinsdale and Napervilleyou’ll love Jupiter
06If you loveBarrington Hillsyou’ll love Wellington
07If you loveLake Geneva weekendsyou’ll love Stuart
Where Your Matches Are
Tap a pin to jump to that match. Map data © OpenStreetMap contributors.
Client reviews
What Out-of-State Clients Say About Working With Monika
Verbatim reviews from Zillow and Google, from clients who bought, sold or rented here while living somewhere else.
Buying from out of state
We Are Your Eyes and Ears Down Here
Most of our relocation clients start from a distance. Before you fly down, my team and I walk the communities, video the homes, read the documents and the club rules, and send you notes.
When you visit, the days are planned around what is left to decide. After the offer, we line up the inspections and insurance quotes and stay on top of every step to closing, whether you are here or in Chicago.
Reviews are verbatim from Zillow and Google; some predate Monika’s move to Douglas Elliman.
“We were buying from out of state and she went to potential homes to video apartments we saw online… we finally decided to move from NY to Florida.”
“Moved from out of state and had constant communication before I arrived for a site visit… She is a great local resource!!”
“We were from out of state and only had 2 days to look at homes. Monika was able to orient us to the area very quickly.”
“We were moving from the Northeast to the Jupiter area and needed knowledgeable help to guide us through the process since we were not on the ground.”
“Monika single-handedly made my move to Florida possible, that is not an exaggeration!!”
“She took the lead and we were able to follow, even from quite a distance away. She made everything smooth and easy.”
“What truly set her apart was the level of care and support she provided while I was out of state.”
“Monika made it very easy for us by being our eyes and ears at the site… without us having to make any trips to the area.”
“I accepted a job in West Palm Beach and had 3 weeks to find an apartment and move down from NY… I can't thank Monika enough.”
“I also really appreciated how well informed she kept me- despite me being out of state during this process.”
“I sold my property in Florida whilst living overseas with Monika's help!!”
Selected verbatim reviews from Zillow and Google, October 2026; some predate Monika’s move to Douglas Elliman. No reviewer was paid. Individual experiences; results vary.
If You Love The Gold Coast, You’ll Love Palm Beach
The Gold Coast's walkable blocks of vintage co-ops, a short walk from the lake and Oak Street, translate neatly to Palm Beach: postwar co-ops and quiet avenues on an island, with Worth Avenue for Oak Street and the Atlantic for Lake Michigan.
New: Phipps Ocean Park is being rebuilt with restored dunes, 80,000 native plants, a relocated Little Red Schoolhouse and new beach pavilions (WLRN, November 2025). (WLRN (opens in a new tab), 2025-11-18)
Palm Beach grew from a pioneer settlement on the lake into a resort town in a single generation. The railroad, the hotels and the bridges set the shape of the island, and the Town still guards it today.
Every home for sale in Palm Beach (opens in a new tab) The Palm Beach guide 246 for sale now (live from BeachesMLS; changes through the day)
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
The Gold Coast and Palm Beach
What to do and see
If You Love It There, Try This Here
Restaurants
4 matchesLong-running bar and dining rooms on a busy shopping street.
Clubby rooms set up for a dressed-up dinner.
Raw bar, fresh fish and a lively room for seafood nights.
French-accented cooking in a polished room steps from the shops.
Nightlife
2 matchesLong-running bars where the night goes late, on the main street out.
Polished rooms for a cocktail and a late dinner; dress up a little.
Coffee
2 matchesEuropean pastries and espresso at a small counter in town.
Bright cafés for coffee, pastries and a light lunch.
Beaches, Parks and the Water
2 matchesPublic beach a short walk from the main shopping street.
Waterfront paths for a morning walk, run or bike ride.
Things to Do
2 matchesGilded Age mansions kept as museums, with period rooms intact.
A few walkable blocks of designer boutiques and window shopping.
Neighborhoods
Neighborhoods, Side by Side
| The Gold Coast | Palm Beach | What they share |
|---|---|---|
| Astor Street District Landmark district of 19th-century mansions and rowhouses on quiet, tree-lined blocks. | Royal Park Addition See homes in this community (opens in a new tab) | Older in-town homes on quiet streets a short walk from shops. |
| East Lake Shore Drive One block of vintage co-op buildings facing the lake. | Lake Drive Co-op No homes are listed for sale here right now. New listings come up through the year; ask me to watch for one. | Co-op living in established buildings looking straight onto the water. |
| Lake Shore Drive high-rises Condo towers lining the lakefront with long water views. | Sloan's Curve See homes in this community (opens in a new tab) | Condo towers on the water with views from every floor. |
More to explore
More Neighborhoods Worth Noting in Palm Beach
For the beach lover
Sloan's Curve: Gated oceanfront condominiums on South Ocean Boulevard.
See homes in Sloan's Curve (opens in a new tab) 8 for sale now
Two North Breakers Row: Oceanfront residences on The Breakers grounds.
See homes in Two North Breakers Row (opens in a new tab) 3 for sale now
For walking everywhere
Palm Beach Towers: An in-town condominium on Cocoanut Row, near Royal Poinciana Way.
See homes in Palm Beach Towers (opens in a new tab) 6 for sale now
Royal Park Addition: Houses and apartments on the avenues between Royal Palm Way and Worth Avenue.
See homes in Royal Park Addition (opens in a new tab) 27 for sale now
For ocean-to-lake estates
Primavera Estates: Estate lots on Clarke, Barton and Primavera Avenues, in lake front, middle and ocean sections.
See homes in Primavera Estates (opens in a new tab) 4 for sale now
For life on the lagoon
Ibis Isle: Houses and condominiums on an island in the Lake Worth Lagoon.
See homes in Ibis Isle (opens in a new tab) 7 for sale now
Questions
Questions About Palm Beach If You Love The Gold Coast
Is Palm Beach like The Gold Coast?
The Gold Coast's walkable blocks of vintage co-ops, a short walk from the lake and Oak Street, translate neatly to Palm Beach: postwar co-ops and quiet avenues on an island, with Worth Avenue for Oak Street and the Atlantic for Lake Michigan.
Where should I eat in Palm Beach if I love the restaurants in The Gold Coast?
If you love Gibsons Bar & Steakhouse in Gold Coast, try Ta-boó. If you love RL Restaurant in Magnificent Mile, try Café L'Europe. If you love Hugo's Frog Bar & Fish House in Gold Coast, try The Seafood Bar at The Breakers.
What is the nightlife like in Palm Beach compared with The Gold Coast?
If Butch McGuire's in Gold Coast is your kind of night, try Cucina Palm Beach: long-running bars where the night goes late, on the main street out. If Maple & Ash in Gold Coast is your kind of night, try HMF at The Breakers: polished rooms for a cocktail and a late dinner; dress up a little.
What are the coffee shops, beaches and parks like in Palm Beach compared with The Gold Coast?
Hendrickx Belgian Bread Crafter pairs with Sant Ambroeus Palm Beach. Goddess and the Baker pairs with Drift Palm Beach. Oak Street Beach pairs with Midtown Municipal Beach. Lakefront Trail pairs with Lake Drive Park.
Which Palm Beach neighborhoods feel like The Gold Coast?
Astor Street District: look at Royal Park Addition (Older in-town homes on quiet streets a short walk from shops). East Lake Shore Drive: look at Lake Drive Co-op (Co-op living in established buildings looking straight onto the water). Lake Shore Drive high-rises: look at Sloan's Curve (Condo towers on the water with views from every floor). See every one in our Palm Beach neighborhood guides.
What is different about living in Palm Beach compared with The Gold Coast?
The vibe: Vintage co-ops on tree-lined blocks by the lake in The Gold Coast; Postwar co-ops and condos on quiet avenues, busiest November to April in Palm Beach. The beaches: Oak Street and North Avenue beaches, swimmable in summer in The Gold Coast; Midtown Beach and Phipps Ocean Park, swimmable most of the year in Palm Beach. On the water: Lake Michigan and the harbors along the lakefront in The Gold Coast; The Atlantic on one side, the Lake Worth Lagoon on the other in Palm Beach. Golf and clubs: City clubs downtown and the Chicago Yacht Club on the lake in The Gold Coast; Private clubs like the Everglades Club and the Bath and Tennis Club, plus The Breakers in Palm Beach. Evenings out: Division Street bars and the lounge upstairs at Maple & Ash in The Gold Coast; Late nights at Cucina on Royal Poinciana Way, cocktails at HMF in The Breakers in Palm Beach. The homes: Co-ops, condominiums and greystones in The Gold Coast; Co-ops, condominiums, in-town houses and ocean-to-lake estates in Palm Beach. Getting back to Chicago: Already home; about 40 minutes to O'Hare in traffic in The Gold Coast; About 15 minutes to the West Palm Beach airport; nonstops to O'Hare all year, about 3 hours in Palm Beach.
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If You Love Streeterville and the West Loop, You’ll Love West Palm Beach
If you like a tower with a view and restaurants downstairs, West Palm Beach is the place. New buildings line Flagler Drive on the Intracoastal, and downtown is growing with new offices and restaurants.
New: The Nora District enters its third phase with Nora House, an 11-story building of 117 condos; groundbreaking expected 2027, completion 2029. (WFLX (opens in a new tab), 2026-04-10)
West Palm Beach began as Henry Flagler’s town across the lake from his Palm Beach hotels. The railroad, the boom and the bust, and the arts that came later shaped the neighborhoods buyers look at today.
Every home for sale in West Palm Beach (opens in a new tab) The West Palm Beach guide 1,670 for sale now (live from BeachesMLS; changes through the day)
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
Streeterville and the West Loop and West Palm Beach
What to do and see
If You Love It There, Try This Here
Restaurants
4 matchesChef-owned rooms with a menu built around the chef's own style.
Diner counters and booths serving burgers, eggs and late-night plates.
Italian kitchens turning out pasta and wood-fired dishes.
Italian dining rooms downtown looking out over the water.
Nightlife
2 matchesRooftop bars with views across the water to the skyline.
Live music with food and drinks, from local bands to national names.
Coffee
2 matchesHometown roasters pouring their own beans at the bar.
Downtown coffee bars in a busy restaurant district.
Beaches, Parks and the Water
1 matchDowntown waterfront promenade with places to sit, eat and watch boats.
Things to Do
2 matchesMajor art museums with deep American and European collections.
Big downtown stages for opera, concerts and touring shows.
Neighborhoods
Neighborhoods, Side by Side
| Streeterville and the West Loop | West Palm Beach | What they share |
|---|---|---|
| Streeterville lakefront towers High-rise condos between Michigan Avenue and the lake, with water views. | Trianon See homes in this community (opens in a new tab) | Condo towers on the water with downtown a short walk away. |
| Fulton Market District Former warehouse blocks turned into lofts, new towers and restaurant rows. | CityPlace South Tower See homes in this community (opens in a new tab) | Tower living above a district of restaurants and shops. |
| Randolph Restaurant Row Stretch of West Randolph Street lined with restaurants and bars. | Northwood Village No homes are listed for sale here right now. New listings come up through the year; ask me to watch for one. | Walkable strip of independent restaurants, bars and shops. |
| Jackson Boulevard Historic District Block of restored 19th-century rowhouses in the West Loop. | Flamingo Park See homes in this community (opens in a new tab) | Historic district of restored older homes near downtown. |
More to explore
More Neighborhoods Worth Noting in West Palm Beach
For something new
The Bristol: A 25-story tower on South Flagler Drive, completed 2019.
See homes in The Bristol (opens in a new tab) 4 for sale now
La Clara: 83 residences on South Flagler, closings from 2023.
See homes in La Clara (opens in a new tab) 3 for sale now
Forté on Flagler: A 25-story tower on South Flagler, with closings since July 2025.
See homes in Forté on Flagler (opens in a new tab) 5 for sale now
For boaters
One Watermark Place: Large residences above a 22-slip marina.
See homes in One Watermark Place (opens in a new tab) 1 for sale now
For old Florida charm
El Cid: A historic district of 1920s and postwar homes along South Flagler Drive.
See homes in El Cid (opens in a new tab) 9 for sale now
Flamingo Park: A 1920s historic district just south of downtown.
See homes in Flamingo Park (opens in a new tab) 9 for sale now
Old Northwood: A 1920s land-boom historic district north of downtown.
See homes in Old Northwood (opens in a new tab) 9 for sale now
For a newer single-family home
Banyan Cay: Single-family homes inside Banyan Cay Resort, on the former President Country Club land.
See homes in Banyan Cay (opens in a new tab) 22 for sale now
New construction
New Construction, Side by Side
| Streeterville and the West Loop | West Palm Beach | What they share |
|---|---|---|
| The Residences at The St. Regis Chicago | Mandarin Oriental Residences, West Palm Beach | Hotel-branded condo tower with hotel services on site. |
Questions
Questions About West Palm Beach If You Love Streeterville and the West Loop
Is West Palm Beach like Streeterville and the West Loop?
If you like a tower with a view and restaurants downstairs, West Palm Beach is the place. New buildings line Flagler Drive on the Intracoastal, and downtown is growing with new offices and restaurants.
Where should I eat in West Palm Beach if I love the restaurants in Streeterville and the West Loop?
If you love Girl & the Goat in West Loop, try Kitchen. If you love Au Cheval in West Loop, try Howley's. If you love Monteverde in West Loop, try Grato.
What is the nightlife like in West Palm Beach compared with Streeterville and the West Loop?
If Offshore Rooftop in Navy Pier, Streeterville is your kind of night, try Spruzzo at The Ben: rooftop bars with views across the water to the skyline. If City Winery Chicago in West Loop is your kind of night, try Clematis by Night: live music with food and drinks, from local bands to national names.
What are the coffee shops, beaches and parks like in West Palm Beach compared with Streeterville and the West Loop?
Intelligentsia Coffee pairs with Pumphouse Coffee Roasters, The Pouratorium. Sawada Coffee pairs with Subculture Coffee (Clematis). Chicago Riverwalk pairs with West Palm Beach Waterfront and Lake Pavilion.
Which West Palm Beach neighborhoods feel like Streeterville and the West Loop?
Streeterville lakefront towers: look at Trianon (Condo towers on the water with downtown a short walk away). Fulton Market District: look at CityPlace South Tower (Tower living above a district of restaurants and shops). Randolph Restaurant Row: look at Northwood Village (Walkable strip of independent restaurants, bars and shops). Jackson Boulevard Historic District: look at Flamingo Park (Historic district of restored older homes near downtown). See every one in our West Palm Beach neighborhood guides.
Is there new construction in West Palm Beach like Streeterville and the West Loop?
If The Residences at The St. Regis Chicago is on your list, look at Mandarin Oriental Residences, West Palm Beach: Hotel-branded condo tower with hotel services on site. More in Palm Beach County new developments.
What is different about living in West Palm Beach compared with Streeterville and the West Loop?
The vibe: High-rises, restaurant rows and offices by the lake and the river in Streeterville and the West Loop; New towers on the Intracoastal and a walkable downtown that keeps adding offices and restaurants in West Palm Beach. The beaches: Ohio Street and Oak Street beaches in summer in Streeterville and the West Loop; No ocean beach in town; Palm Beach's Midtown Beach is across the bridge in West Palm Beach. On the water: Lake Michigan, Navy Pier and the Chicago River in Streeterville and the West Loop; The Intracoastal along Flagler Drive, with Peanut Island a short boat ride north in West Palm Beach. Golf and clubs: City clubs downtown; golf means a drive to the suburbs in Streeterville and the West Loop; Club golf across the county, and the Palm Beach clubs across the bridge in West Palm Beach. Evenings out: Rooftop drinks at Navy Pier, concerts at City Winery in the West Loop in Streeterville and the West Loop; Rooftop drinks at Spruzzo, free Thursday concerts at Clematis by Night in West Palm Beach. The homes: Condo towers and converted lofts in Streeterville and the West Loop; New condo towers downtown and 1920s houses in historic districts beside it in West Palm Beach. Getting back to Chicago: Already downtown; about 30 to 45 minutes to O'Hare, or the Blue Line train in Streeterville and the West Loop; About 10 minutes to the West Palm Beach airport; nonstops to O'Hare all year, about 3 hours in West Palm Beach.
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If You Love Lake Forest, You’ll Love Palm Beach Gardens
Lake Forest's old clubs and big lots point straight to Palm Beach Gardens, where private golf clubs set the rhythm of the week and the homes sit inside the gate.
New: Publix opened May 21, 2026 at Avenir Town Center on Northlake Boulevard. (Publix Corporate Newsroom (opens in a new tab), 2026-05-21)
Palm Beach Gardens was a plan on paper before it was a place. One landowner’s idea of a garden city, and the golf that followed, shaped the neighborhoods buyers choose between today.
Every home for sale in Palm Beach Gardens (opens in a new tab) The Palm Beach Gardens guide 603 for sale now (live from BeachesMLS; changes through the day)
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
Lake Forest and Palm Beach Gardens
What to do and see
If You Love It There, Try This Here
Restaurants
2 matchesA dining room and a pub-style bar from the same chef, side by side.
Polished dinner rooms in a shopping center setting.
Nightlife
2 matchesClassic hotel bars for a cocktail in a quiet, polished room.
A casual pint close to home, without a trip downtown.
Beaches, Parks and the Water
1 matchProtected native landscape with trails and boardwalks for birding.
Things to Do
1 matchOpen-air shops and restaurants around a central gathering space.
Neighborhoods
Neighborhoods, Side by Side
| Lake Forest | Palm Beach Gardens | What they share |
|---|---|---|
| Onwentsia Club area Historic private golf club founded in 1895, ringed by estates on deep lots. | Frenchman's Creek See homes in this community (opens in a new tab) | Long-established private club with golf at the center of the community. |
| Knollwood Club Private golf club in Lake Forest with homes on wooded lots nearby. | BallenIsles See homes in this community (opens in a new tab) | Private golf club community with tennis and a clubhouse calendar. |
| Lake Forest east side estates Large homes on deep, wooded lots between downtown and the lake. | Old Palm Golf Club See homes in this community (opens in a new tab) | Large custom homes on generous lots inside a private club. |
More to explore
More Neighborhoods Worth Noting in Palm Beach Gardens
For golf and club life
BallenIsles: Three courses and an equity club.
See homes in BallenIsles (opens in a new tab) 28 for sale now
Old Palm: About 300 homes on 650 acres around one private course.
See homes in Old Palm (opens in a new tab) 5 for sale now
Mirasol: Two courses and 23 neighborhoods.
See homes in Mirasol (opens in a new tab) 10 for sale now
For boaters
Frenchman's Creek: Deep-water lots, 36 holes and a beach club.
See homes in Frenchman's Creek (opens in a new tab) 17 for sale now
For golf without a required membership
PGA National: Four championship courses plus a par-3, thousands of homes, with club membership optional.
See homes in PGA National (opens in a new tab) 102 for sale now
For no club at all
Evergrene: Homes around Lake Dorothy, with no club equity.
See homes in Evergrene (opens in a new tab) 22 for sale now
Questions
Questions About Palm Beach Gardens If You Love Lake Forest
Is Palm Beach Gardens like Lake Forest?
Lake Forest's old clubs and big lots point straight to Palm Beach Gardens, where private golf clubs set the rhythm of the week and the homes sit inside the gate.
Where should I eat in Palm Beach Gardens if I love the restaurants in Lake Forest?
If you love Deer Path Inn in Lake Forest, try Coolinary and The Parched Pig. If you love Le Colonial Lake Forest in Market Square, try Café Chardonnay.
What is the nightlife like in Palm Beach Gardens compared with Lake Forest?
If The Bar at the Deer Path Inn in Lake Forest is your kind of night, try Lobby Bar at PGA National Resort: classic hotel bars for a cocktail in a quiet, polished room. If White Hart Pub at the Deer Path Inn in Lake Forest is your kind of night, try Twisted Trunk Brewing: a casual pint close to home, without a trip downtown.
What are the coffee shops, beaches and parks like in Palm Beach Gardens compared with Lake Forest?
Middlefork Savanna Forest Preserve pairs with Frenchman's Forest Natural Area.
Which Palm Beach Gardens neighborhoods feel like Lake Forest?
Onwentsia Club area: look at Frenchman's Creek (Long-established private club with golf at the center of the community). Knollwood Club: look at BallenIsles (Private golf club community with tennis and a clubhouse calendar). Lake Forest east side estates: look at Old Palm Golf Club (Large custom homes on generous lots inside a private club). See every one in our Palm Beach Gardens neighborhood guides.
What is different about living in Palm Beach Gardens compared with Lake Forest?
The vibe: Old estates, deep lots and private clubs on the North Shore in Lake Forest; Gated club communities with golf, tennis and dining on site in Palm Beach Gardens. The beaches: Forest Park Beach on Lake Michigan, in summer in Lake Forest; Juno Beach and Jupiter, about 10 to 15 minutes east, all year in Palm Beach Gardens. On the water: Lake Michigan, for the warm months in Lake Forest; The Intracoastal along PGA Boulevard, with marinas and the ocean nearby in Palm Beach Gardens. Golf and clubs: Private clubs like Onwentsia, Shoreacres and Knollwood in Lake Forest; Many private clubs in one city, like Old Palm, Mirasol, BallenIsles and PGA National in Palm Beach Gardens. Evenings out: A drink at the Deer Path Inn's bar or the White Hart Pub in Lake Forest; A cocktail at the PGA National lobby bar, a pint at Twisted Trunk Brewing in Palm Beach Gardens. The homes: Estates and Georgian houses on deep lots in Lake Forest; Custom estates and club homes inside the gate in Palm Beach Gardens. Getting back to Chicago: About an hour by car or the Metra train into the city in Lake Forest; About 25 minutes to the West Palm Beach airport; nonstops to O'Hare all year, about 3 hours in Palm Beach Gardens.
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If You Love Winnetka and Kenilworth, You’ll Love Jupiter Island and Hobe Sound
The quiet, leafy streets and lakefront of Winnetka have their match on Jupiter Island: estate homes between the ocean and the Intracoastal, the Jupiter Island Club and no commercial strip.
New: A mixed-use project is proposed at 9025 SE Bridge Road in downtown Hobe Sound: about 4,399 sq ft of restaurant and retail space, three apartments and six townhouses (Martin County applications, February 2026). (TreasureCoast.com (opens in a new tab), 2026-02)
Jupiter Island was a Spanish land grant, a pineapple venture and a winter resort before it became a town. The club, the preserves and the beach program that shape it today date from the 1930s to the 1980s.
Every home for sale in Jupiter Island and Hobe Sound (opens in a new tab) 18 for sale now (live from BeachesMLS; changes through the day)
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
Winnetka and Kenilworth and Jupiter Island and Hobe Sound
What to do and see
If You Love It There, Try This Here
Nightlife
2 matchesNeighborhood rooms with live music on a regular calendar.
Outdoor concerts on a lawn by the water or the trees, a short drive from home.
Beaches, Parks and the Water
1 matchQuiet public beach below the bluffs, away from crowds.
Neighborhoods
Neighborhoods, Side by Side
| Winnetka and Kenilworth | Jupiter Island and Hobe Sound | What they share |
|---|---|---|
| Sheridan Road lakefront estates Estate homes on the bluffs along Lake Michigan. | Jupiter Island | Estate homes on large lots right on the water. |
| Kenilworth Small planned village of large homes, leafy streets and almost no commerce. | Jupiter Island Club See homes in this community (opens in a new tab) | Quiet residential enclave organized around one club. |
More to explore
More Neighborhoods Worth Noting in Jupiter Island and Hobe Sound
For quiet and privacy
Jupiter Island Club: A 1944 club at the center of a 2.7-square-mile town.
See homes in Jupiter Island Club (opens in a new tab) 13 for sale now
For boaters
Loblolly: In Hobe Sound across the Intracoastal from Jupiter Island: homes on the Intracoastal with a private marina and club.
See homes in Loblolly (opens in a new tab) 6 for sale now
Questions
Questions About Jupiter Island and Hobe Sound If You Love Winnetka and Kenilworth
Is Jupiter Island and Hobe Sound like Winnetka and Kenilworth?
The quiet, leafy streets and lakefront of Winnetka have their match on Jupiter Island: estate homes between the ocean and the Intracoastal, the Jupiter Island Club and no commercial strip.
What is the nightlife like in Jupiter Island and Hobe Sound compared with Winnetka and Kenilworth?
If SPACE in Evanston is your kind of night, try Harry and the Natives: neighborhood rooms with live music on a regular calendar. If Ravinia Festival in Highland Park is your kind of night, try Harbourside Place: outdoor concerts on a lawn by the water or the trees, a short drive from home.
What are the coffee shops, beaches and parks like in Jupiter Island and Hobe Sound compared with Winnetka and Kenilworth?
Tower Road Park pairs with Hobe Sound Beach.
Which Jupiter Island and Hobe Sound neighborhoods feel like Winnetka and Kenilworth?
Sheridan Road lakefront estates: look at Jupiter Island (Estate homes on large lots right on the water). Kenilworth: look at Jupiter Island Club (Quiet residential enclave organized around one club). See every one in our Jupiter Island and Hobe Sound neighborhood guides.
What is different about living in Jupiter Island and Hobe Sound compared with Winnetka and Kenilworth?
The vibe: Quiet, leafy streets by the lake in Winnetka and Kenilworth; Quiet and green, with the ocean on one side and the Intracoastal on the other in Jupiter Island and Hobe Sound. The beaches: Tower Road and Elder Lane beaches, in summer in Winnetka and Kenilworth; Ocean beach along the island, including Blowing Rocks Preserve in Jupiter Island and Hobe Sound. On the water: Lake Michigan and the harbors up the shore in Winnetka and Kenilworth; Private docks on the Intracoastal, and the Jupiter Inlet at the south end in Jupiter Island and Hobe Sound. Golf and clubs: Indian Hill Club and Skokie Country Club in Winnetka and Kenilworth; The Jupiter Island Club, with Loblolly and The Medalist in Hobe Sound in Jupiter Island and Hobe Sound. Evenings out: Concerts at SPACE in Evanston and on the lawn at Ravinia in Winnetka and Kenilworth; Live music at Harry and the Natives in Hobe Sound, concerts at Harbourside Place in Jupiter Island and Hobe Sound. The homes: Estates on the lake bluffs and wooded lots in Winnetka and Kenilworth; Estate homes on large lots, many with docks in Jupiter Island and Hobe Sound. Getting back to Chicago: About 40 minutes by car or the Metra train downtown in Winnetka and Kenilworth; 45 to 60 minutes to the West Palm Beach airport; O'Hare nonstops all year, about 3 hours in Jupiter Island and Hobe Sound.
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If You Love Hinsdale and Naperville, You’ll Love Jupiter
If you want a neighborhood with parks, a club and a downtown you can walk to, Jupiter fits. Abacoa has its own downtown, and the beach is about fifteen minutes away.
New: Voloridge Investment Management bought parts of Harbourside Place for $57.6 million and plans a new office building for up to 200 employees. (Commercial Observer (opens in a new tab), 2026-02-20)
People have lived at the Jupiter Inlet for thousands of years. The inlet, the river and the lighthouse shaped the town, and they still shape its neighborhoods today.
Every home for sale in Jupiter (opens in a new tab) The Jupiter guide 563 for sale now (live from BeachesMLS; changes through the day)
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
Hinsdale and Naperville and Jupiter
What to do and see
If You Love It There, Try This Here
Restaurants
3 matchesSeafood and steaks in a busy room built for a night out.
Casual neighborhood kitchens where regulars know the specials.
Big, rambling spots with outdoor seating made for a long afternoon.
Nightlife
2 matchesA walkable downtown where a pint and dinner turn into live music.
Stages that host touring bands as well as local acts.
Coffee
2 matchesLocal roasters with a café counter in town.
Downtown stops for a pastry and coffee before errands.
Beaches, Parks and the Water
2 matchesPaved riverside paths linking parks, restaurants and downtown.
Sheltered swimming water with lawns and picnic space.
Things to Do
2 matchesOutdoor history sites with tours and restored historic buildings.
Professional theaters staging Broadway-style musicals close to home.
Neighborhoods
Neighborhoods, Side by Side
| Hinsdale and Naperville | Jupiter | What they share |
|---|---|---|
| Hinsdale Golf Club area Homes around a private golf club founded in 1898. | The Loxahatchee Club See homes in this community (opens in a new tab) | Private golf club with homes set along the fairways. |
More to explore
More Neighborhoods Worth Noting in Jupiter
For the beach lover
Jupiter Inlet Colony: Its own small town beside Jupiter, with homes on the ocean, the inlet and quiet interior streets.
Ocean Trail: Five oceanfront condominium buildings on A1A.
See homes in Ocean Trail (opens in a new tab) 25 for sale now
For boaters
Jupiter Yacht Club: Intracoastal residences above a 79-slip marina.
See homes in Jupiter Yacht Club (opens in a new tab) 4 for sale now
Pennock Point: An ungated Loxahatchee River peninsula in unincorporated Jupiter, with no HOA and private docks.
See homes in Pennock Point (opens in a new tab) 1 for sale now
For golf and club life
Admirals Cove: 45 holes and a full-service marina in a gated club community.
See homes in Admirals Cove (opens in a new tab) 42 for sale now
The Bear's Club: Estates and villas around a private Jack Nicklaus course, behind a gate.
See homes in The Bear's Club (opens in a new tab) 9 for sale now
For room to spread out
Jupiter Farms: About 15 square miles of unincorporated acreage west of Jupiter, with a county riding park.
See homes in Jupiter Farms (opens in a new tab) 55 for sale now
For something newer
Jupiter Country Club: Toll Brothers homes around a Greg Norman course now being redesigned by Agustín Pizá.
See homes in Jupiter Country Club (opens in a new tab) 15 for sale now
For a walkable town center
Abacoa: A planned community of distinct neighborhoods, a public golf club and Downtown Abacoa.
See homes in Abacoa (opens in a new tab) 56 for sale now
Questions
Questions About Jupiter If You Love Hinsdale and Naperville
Is Jupiter like Hinsdale and Naperville?
If you want a neighborhood with parks, a club and a downtown you can walk to, Jupiter fits. Abacoa has its own downtown, and the beach is about fifteen minutes away.
Where should I eat in Jupiter if I love the restaurants in Hinsdale and Naperville?
If you love Hugo's Frog Bar & Fish House in Naperville, try Jetty's Waterfront Restaurant. If you love Fuller House in Hinsdale, try Little Moir's Food Shack. If you love Two Brothers Roundhouse in Aurora, try Guanabanas.
What is the nightlife like in Jupiter compared with Hinsdale and Naperville?
If Quigley's Irish Pub in Naperville is your kind of night, try Harbourside Place: a walkable downtown where a pint and dinner turn into live music. If Arcada Theatre in St. Charles is your kind of night, try Guanabanas: stages that host touring bands as well as local acts.
What are the coffee shops, beaches and parks like in Jupiter compared with Hinsdale and Naperville?
Sparrow Coffee pairs with Pumphouse Coffee Roasters, Cones & Coffee. Toni Patisserie & Café pairs with Subculture Coffee (Jupiter). Naperville Riverwalk pairs with Jupiter Riverwalk. Centennial Beach pairs with DuBois Park.
Which Jupiter neighborhoods feel like Hinsdale and Naperville?
Hinsdale Golf Club area: look at The Loxahatchee Club (Private golf club with homes set along the fairways). See every one in our Jupiter neighborhood guides.
What is different about living in Jupiter compared with Hinsdale and Naperville?
The vibe: Suburbs built around good streets, parks and a downtown in Hinsdale and Naperville; Neighborhoods built around parks, golf and the water, busiest in winter in Jupiter. The beaches: Centennial Beach in Naperville, a summer swim in Hinsdale and Naperville; Carlin Park and Jupiter Beach Park, with water warm enough to swim most of the year in Jupiter. On the water: The DuPage River and the Naperville Riverwalk in Hinsdale and Naperville; The Jupiter Inlet, the Loxahatchee River and the Intracoastal, with offshore fishing all year in Jupiter. Golf and clubs: Hinsdale Golf Club and Medinah Country Club nearby in Hinsdale and Naperville; Public golf at Abacoa, private clubs like Admirals Cove and The Loxahatchee Club in Jupiter. Evenings out: A pint and music at Quigley's in downtown Naperville, concerts at the Arcada in Hinsdale and Naperville; Dinner and free concerts at Harbourside Place, live music at Guanabanas in Jupiter. The homes: Single-family homes on tree-lined streets in Hinsdale and Naperville; Single-family homes, club homes and newer construction in Jupiter. Getting back to Chicago: About 30 minutes to an hour by car, or the Metra train downtown in Hinsdale and Naperville; About 30 minutes to the West Palm Beach airport; nonstops to O'Hare all year, about 3 hours in Jupiter.
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If You Love Barrington Hills, You’ll Love Wellington
Barrington Hills' acreage and horse trails continue in Wellington, where barns, riding trails and the winter show-jumping and polo seasons are part of everyday life.
New: Related Ross bought 32 acres near State Road 7 for Village Landing, planned with a 180-room hotel and 300,000+ square feet of shops, offices and restaurants. (Commercial Observer (opens in a new tab), 2026-09-01)
Wellington is one of the newest towns in the county: a ranch in the 1950s, a planned community in the 1970s and a village since 1995. Horses came with the polo club and never left.
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
Barrington Hills and Wellington
What to do and see
If You Love It There, Try This Here
Restaurants
3 matchesSpecial-occasion dining rooms in horse country.
Steaks and grilled meats in a rustic, country setting.
Local American restaurants for an easy dinner close to home.
Nightlife
2 matchesLocal spots with a kitchen and live bands on weekend nights.
Concerts on the lawn; bring a chair or a blanket.
Coffee
1 matchLocal coffee shops for a quick stop between barn and errands.
Beaches, Parks and the Water
1 matchWetland trails and boardwalks with birds and open water.
Things to Do
1 matchLocal venues for movies and shows in town.
Neighborhoods
Neighborhoods, Side by Side
| Barrington Hills | Wellington | What they share |
|---|---|---|
| Barrington Hills horse farms Farms and estates on five-acre-plus lots with barns and paddocks. | Palm Beach Point See homes in this community (opens in a new tab) | Equestrian estates on acreage with barns and paddocks. |
| Riding Club of Barrington Hills trails Private bridle trail network linking farms across the village. | Saddle Trail Park See homes in this community (opens in a new tab) | Horse-friendly roads and bridle paths connecting farms. |
| Barrington Hills Country Club Private golf and country club with homes nearby. | Wycliffe Golf and Country Club See homes in this community (opens in a new tab) | Golf and country club life alongside horse country. |
More to explore
More Neighborhoods Worth Noting in Wellington
For room to ride
Palm Beach Point: Farm parcels in Wellington’s equestrian district.
See homes in Palm Beach Point (opens in a new tab) 7 for sale now
Saddle Trail Park: Acreage lots in the equestrian district.
See homes in Saddle Trail Park (opens in a new tab) 11 for sale now
Next to the show grounds
Grand Prix Village: Horse farms near the Wellington International show grounds.
No homes are listed for sale here right now. New listings come up through the year; ask me to watch for one.
For polo
Southfields: Horse properties and estate homes near Palm Beach Polo Golf & Country Club.
See homes in Southfields (opens in a new tab) 5 for sale now
For golf
Binks Forest: Homes around Wellington National, a Johnny Miller course.
See homes in Binks Forest (opens in a new tab) 16 for sale now
Questions
Questions About Wellington If You Love Barrington Hills
Is Wellington like Barrington Hills?
Barrington Hills' acreage and horse trails continue in Wellington, where barns, riding trails and the winter show-jumping and polo seasons are part of everyday life.
Where should I eat in Wellington if I love the restaurants in Barrington Hills?
If you love The Greggory in South Barrington, try Stallion Restaurant. If you love Barn of Barrington in Barrington, try Rancho Argentino. If you love Region in Barrington, try Oli's Fashion Cuisine.
What is the nightlife like in Wellington compared with Barrington Hills?
If Durty Nellie's in Palatine is your kind of night, try Village Music Wellington: local spots with a kitchen and live bands on weekend nights. If Ravinia Festival in Highland Park is your kind of night, try Wellington Amphitheater: concerts on the lawn; bring a chair or a blanket.
What are the coffee shops, beaches and parks like in Wellington compared with Barrington Hills?
Conscious Cup Coffee pairs with Foxtail Coffee Co. (Wellington). Crabtree Nature Center pairs with Peaceful Waters Sanctuary.
Which Wellington neighborhoods feel like Barrington Hills?
Barrington Hills horse farms: look at Palm Beach Point (Equestrian estates on acreage with barns and paddocks). Riding Club of Barrington Hills trails: look at Saddle Trail Park (Horse-friendly roads and bridle paths connecting farms). Barrington Hills Country Club: look at Wycliffe Golf and Country Club (Golf and country club life alongside horse country). See every one in our Wellington neighborhood guides.
What is different about living in Wellington compared with Barrington Hills?
The vibe: Rolling acreage and horse trails in Barrington Hills; Horse country, with barns, riding trails, show grounds and polo fields in Wellington. The outdoors: Bridle trails and forest preserves, at their peak in summer in Barrington Hills; Riding trails and show grounds all winter; the beach is about 30 minutes east in Wellington. The season: Summer riding in Barrington Hills; The winter equestrian season and the polo season set the calendar in Wellington. Golf and clubs: Barrington Hills Country Club and the Barrington Hills Riding Club in Barrington Hills; Palm Beach Polo, Wellington National and the International Polo Club in Wellington. Evenings out: Live bands at Durty Nellie's in Palatine, summer concerts at Ravinia in Barrington Hills; Live bands at Village Music, free concerts at the Wellington Amphitheater in Wellington. The homes: Estates on five acres and up in Barrington Hills; Farms from a few acres to ten and more, in an equestrian district in Wellington. Getting back to Chicago: About an hour by car, or the Metra train from Barrington in Barrington Hills; About 25 minutes to the West Palm Beach airport; nonstops to O'Hare all year, about 3 hours in Wellington.
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If You Love Lake Geneva weekends, You’ll Love Stuart
If the week revolves around the lake house in Wisconsin, Stuart is that feeling full time: a riverfront downtown, marinas and docks on the St. Lucie River, and a slower pace at the north end of the Treasure Coast.
Stuart grew up around the river, the inlet and the railroad. The waterways that drew the first settlers still shape where its neighborhoods are and how they are built.
Every home for sale in Stuart (opens in a new tab) The Stuart guide 786 for sale now (live from BeachesMLS; changes through the day)
See the Full MatchClose the MatchSide by side, places to eat and do, neighborhoods, new construction and questions
Side by side
Lake Geneva weekends and Stuart
What to do and see
If You Love It There, Try This Here
Restaurants
2 matchesSteaks and a full bar for a dressed-up night out.
Dinner and drinks in an older building in the historic part of town.
Nightlife
2 matchesBars on the water with a deck, where a drink comes with the sunset.
Downtown spots that stay busy late, a short walk from the water.
Coffee
1 matchIndependent downtown coffee shops with a local following.
Beaches, Parks and the Water
2 matchesLifeguarded public beach, steps from downtown there, a short drive over the causeway here.
Swimming beach with calm, shallow water for an easy day.
Things to Do
1 matchMuseums of local history, boats and the people who built the town.
Neighborhoods
Neighborhoods, Side by Side
| Lake Geneva weekends | Stuart | What they share |
|---|---|---|
| Downtown Lake Geneva Walkable streets of shops and restaurants by the lakefront. | Downtown Stuart See homes in this community (opens in a new tab) | Walkable historic downtown on the water with shops and dining. |
| Geneva National Gated golf community with three courses near the lake. | Willoughby Golf Club See homes in this community (opens in a new tab) | Gated golf club community with homes on the course. |
More to explore
More Neighborhoods Worth Noting in Stuart
For boaters
Sailfish Point: 532 acres on Hutchinson Island with an 84-slip marina.
See homes in Sailfish Point (opens in a new tab) 24 for sale now
For golf
Mariner Sands: 771 homes and two courses, golf optional.
See homes in Mariner Sands (opens in a new tab) 31 for sale now
For a walkable downtown
Downtown Stuart: Homes on the old riverfront plats of downtown Stuart, from early houses to recent condominiums.
See homes in Downtown Stuart (opens in a new tab) 17 for sale now
For life on the river
North River Shores: Homes on the North Fork of the St. Lucie River, just north of the City of Stuart in unincorporated Martin County.
See homes in North River Shores (opens in a new tab) 4 for sale now
New construction
New Construction, Side by Side
| Lake Geneva weekends | Stuart | What they share |
|---|---|---|
| The Residences of Geneva Lake | Sailfish Cay | New homes close to the water. |
Questions
Questions About Stuart If You Love Lake Geneva weekends
Is Stuart like Lake Geneva weekends?
If the week revolves around the lake house in Wisconsin, Stuart is that feeling full time: a riverfront downtown, marinas and docks on the St. Lucie River, and a slower pace at the north end of the Treasure Coast.
Where should I eat in Stuart if I love the restaurants in Lake Geneva weekends?
If you love Geneva ChopHouse in Grand Geneva, try The Gafford. If you love The Baker House in Lake Geneva, try The Black Marlin.
What is the nightlife like in Stuart compared with Lake Geneva weekends?
If Pier 290 in Williams Bay, Geneva Lake is your kind of night, try Shrimper's Grill: bars on the water with a deck, where a drink comes with the sunset. If Champs Sports Bar & Grill in Lake Geneva is your kind of night, try Terra Fermata: downtown spots that stay busy late, a short walk from the water.
What are the coffee shops, beaches and parks like in Stuart compared with Lake Geneva weekends?
Inspired pairs with The Roasted Record. Riviera Beach pairs with Stuart Beach. Big Foot Beach State Park pairs with Bathtub Beach.
Which Stuart neighborhoods feel like Lake Geneva weekends?
Downtown Lake Geneva: look at Downtown Stuart (Walkable historic downtown on the water with shops and dining). Geneva National: look at Willoughby Golf Club (Gated golf club community with homes on the course). See every one in our Stuart neighborhood guides.
Is there new construction in Stuart like Lake Geneva weekends?
If The Residences of Geneva Lake is on your list, look at Sailfish Cay: New homes close to the water. More in Palm Beach County new developments.
What is different about living in Stuart compared with Lake Geneva weekends?
The vibe: A lake town that fills up on summer weekends in Lake Geneva weekends; A river town with a walkable downtown, busy all year in Stuart. The beaches: Riviera Beach on Geneva Lake, in summer in Lake Geneva weekends; Stuart Beach and Bathtub Reef Beach on Hutchinson Island in Stuart. On the water: Geneva Lake, boats and the lake path in Lake Geneva weekends; The St. Lucie River, the Indian River Lagoon and the St. Lucie Inlet to the ocean in Stuart. Golf and clubs: Lake Geneva Country Club and the Grand Geneva courses in Lake Geneva weekends; Private clubs like Sailfish Point, Mariner Sands and Willoughby in Stuart. Evenings out: Lakefront drinks at Pier 290, a late night downtown at Champs in Lake Geneva weekends; Sunset drinks at Shrimper's on the water, live music at Terra Fermata downtown in Stuart. The homes: Lake houses and cottages in Lake Geneva weekends; River homes, marina communities and downtown condominiums in Stuart. Getting back to Chicago: About 90 minutes by car in Lake Geneva weekends; 50 to 60 minutes to the West Palm Beach airport; O'Hare nonstops all year, about 3 hours in Stuart.
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In their words
What People Ask Before Moving from Chicago
Questions and worries that come up again and again in forums and news coverage, with our answers. Quotes are from public posts and articles, linked to the source.
“I worry about the weather getting boring”
City-Data forum (a City-Data user) (opens in a new tab), 2020
“I miss the good restaurants and taste of good food”
City-Data forum (a City-Data user) (opens in a new tab), 2021
Will I miss Chicago restaurants?
Downtown West Palm (Pistache, Kitchen), Palm Beach Gardens (Café Chardonnay, Coolinary & the Parched Pig) and Palm Beach island. It is a smaller restaurant scene than Chicago's.
Is there anything like the Art Institute or the lakefront?
Norton Museum of Art; the West Palm waterfront on the Lake Worth Lagoon; the Intracoastal as the new lakefront.
Does endless summer get boring? How hot is August?
Summer is long, but the year still turns: a dry season from about November to May and a wet season from June to October.
Should I sell before I buy?
Many buyers rent here first or use a bridge loan. If you are buying a condo, Florida law entitles you to the milestone inspection summary and the latest structural integrity reserve study (SIRS); read both before you commit.
Is this where the Chicago finance people went?
Citadel moved its headquarters to Miami in 2022. West Palm Beach has its own finance cluster; Elliott Management moved its headquarters there in 2020.
Heard This? Here Is the Fact
“Citadel moved to Palm Beach.”
Citadel moved its headquarters to Miami in 2022, not Palm Beach. (source (opens in a new tab))
“Chicago's sales tax gap makes up the difference.”
Illinois' flat 4.95% income tax is the bigger line; Florida has none. Insurance is the main Florida offset. (source (opens in a new tab))
The big question
Is It Worth Moving from Chicago to Palm Beach County?
For most Illinois buyers who can make Florida their real home, yes. Florida has no state income or estate tax, Palm Beach County's median property tax rate is less than half of Illinois's, and O'Hare is about three hours nonstop; the trade is a higher insurance bill and a hot summer that is also hurricane season.
724 tax returns moved from Illinois into Palm Beach and Martin counties in the 2022 to 2023 IRS county-to-county migration data, led by Cook County (487), Lake County (108) and DuPage County (70) (IRS SOI migration data (opens in a new tab)).
| What changes | Chicago | Palm Beach County |
|---|---|---|
| State income tax | Flat 4.95% | None |
| Estate tax | Estates above $4,000,000; it is a threshold, not a credit, so a taxable estate pays on more than the excess | None. Federal exemption $15,000,000 per person in 2026 applies in both states |
| Median effective property tax | 1.88%; Cook County 1.73% | Palm Beach County 0.82%; Martin County 0.76% |
| Leaving the tax system | Illinois taxes its residents on all of their income. | Driver license within 30 days, Declaration of Domicile, homestead by March 1 |
| Home insurance | Usually the smaller bill | Usually the larger bill; wind and flood are priced house by house |
| Flights between the two | O'Hare | Nonstop from West Palm Beach, about three hours |
| Home prices | Varies by town | Town by town; see the live medians |
Taxes and costs
How Do Illinois and Florida Taxes Compare?
Florida has no state income, estate or inheritance tax. Illinois charges a flat 4.95% income tax, taxes estates above $4,000,000, and has a median effective property tax rate of 1.88%, against 0.82% in Palm Beach County. Your own numbers depend on how and where your income is earned, so run them with your CPA.
Illinois’s flat income tax looks modest next to New York’s; the estate tax and the property tax are where the difference adds up. Run your own numbers with your CPA.
| Illinois | Florida | |
|---|---|---|
| State income tax | Flat 4.95% (Illinois Department of Revenue (opens in a new tab)) | None |
| Estate tax | Estates above $4,000,000; it is a threshold, not a credit, so a taxable estate pays on more than the excess (Illinois Attorney General (opens in a new tab)) | None. Federal exemption $15,000,000 per person in 2026 applies in both states |
| Median effective property tax | 1.88%; Cook County 1.73% (Tax Foundation 2026 (opens in a new tab), 2024 data) | Palm Beach County 0.82%; Martin County 0.76% |
| Primary home protections | Homeowner exemptions set by county | Homestead exemption on the first $25,000 plus a second, inflation-indexed $25,000 of assessed value; Save Our Homes 3% cap |
Rates as published for 2025-2026, accessed October 2026. General information, not tax advice.
Florida’s constitution bars a state tax on the income of residents (Fla. Const. Art. VII, s.5 (opens in a new tab)). A home you own and live in as of January 1 can carry the homestead exemption: the first $25,000 of assessed value off all taxes and a second $25,000 (indexed to inflation) off non-school taxes on value above $50,000 (s.196.031 (opens in a new tab)). After the first year, Save Our Homes holds the yearly rise in assessed value to 3% or inflation, whichever is lower (s.193.155 (opens in a new tab)). A second home or rental gets no homestead; its non-school assessment increase is capped at 10% a year (s.193.1554 (opens in a new tab)).
On the November 3, 2026 ballot: Amendment 3 (opens in a new tab) would raise the non-school homestead exemption sharply from 2027 and lower the non-homestead cap from 10% to 5%. As passed by the Legislature, people who are not Florida residents on December 31, 2026 would get the current exemption for their first four years of homestead and the larger one from the fifth year, to the extent the U.S. Constitution allows. If it passes, we will update this page; if timing matters to you, talk to your tax advisor before you close.
Published rates as of October 2026. General information, not tax advice. Your result depends on your income and filing; confirm with your CPA.
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Making Florida home
When Does Illinois Stop Treating Me as a Resident?
Illinois taxes its residents on all of their income, so the move has to be a real change of domicile: where your home, your time, your business and the things you treasure are. Keep records from the first day, and plan the timing with your CPA. The Florida filings below build the record.
- Close on a home you will live inHomestead turns on owning and living in the home as your permanent residence on January 1.
- Florida driver license within 30 daysFlorida asks new residents to switch their license within 30 days of establishing residency (FLHSMV (opens in a new tab)).
- Insure, title and register your carFlorida insurance from a Florida-licensed agent, then title and registration within 10 days of establishing residency. A vehicle titled in another state needs a VIN verification.
- Register to vote at the new addressOnline, at the tax collector or at a driver license office (Florida Division of Elections (opens in a new tab)). The address should match the homestead.
- File a Declaration of DomicileA sworn statement recorded with the Clerk of the Circuit Court in your county (s.222.17 (opens in a new tab)): Palm Beach County Clerk (opens in a new tab) or Martin County Clerk (opens in a new tab).
- Apply for homestead by March 1With the Palm Beach County Property Appraiser (opens in a new tab) or the Martin County Property Appraiser (opens in a new tab). Miss March 1 and the exemption waits a year.
We line up closing with your attorney and CPA so the January 1 homestead date works and the Illinois sale, if there is one, closes in the right year.
Florida filings show intent but do not by themselves end residency in your current state. That state decides under its own rules, so get advice from a tax professional there before you rely on it.
Getting back
How Do I Get Back to Chicago from Palm Beach?
Nonstop flights from West Palm Beach to O'Hare take about three hours, and the airport is about 30 minutes from Jupiter.
President Donald J. Trump International Airport in West Palm Beach (DJT, formerly PBI) flies nonstop to O’Hare on American, with seasonal United service; there is no nonstop to Midway (airport nonstop list (opens in a new tab), October 2026). Fort Lauderdale and Miami airports add more options.
From Jupiter the airport is about 30 minutes without traffic.
Nonstop from DJT, October 2026
- Chicago O’Hare (ORD): American; United (seasonal)
- Detroit (DTW): Delta
- Minneapolis (MSP): Delta (seasonal)
- Indianapolis (IND): Southwest, from Feb. 13, 2027 (seasonal)
- St. Louis (STL): Southwest, from Feb. 11, 2027 (seasonal)
Airlines change routes often; check with the airline before you plan around one.
Before you make an offer
What Should I Know About Insurance and Flood Zones Before I Make an Offer?
Insurance is one of the costs new arrivals most often underestimate, and it turns as much on the house as on the town: roof age and shape, opening protection, elevation and distance to the water all move the premium. We ask for quotes during the inspection period, not after it.
Look up the flood zone for the specific home: FEMA Flood Map Service Center (opens in a new tab), Palm Beach County flood maps (opens in a new tab) (new maps took effect December 20, 2024) or Martin County flood zones (opens in a new tab). A National Flood Insurance Program policy usually starts 30 days after purchase, unless it is bought with the mortgage (FloodSmart (opens in a new tab)).
Citizens Property Insurance is the state’s insurer of last resort. A primary home qualifies only when private offers run more than 20% above Citizens, and Citizens policies now require flood coverage, phased in by home value through January 1, 2027 (s.627.351 (opens in a new tab)).
Ask for these before you commit
- A four-point and a wind mitigation inspection (insurers price the roof, openings and wiring)
- The roof’s age and permit history
- An elevation certificate if the home is in a flood zone
- The seller’s current premium and carrier
- For a condominium: the association’s master policy, reserves and milestone inspection status
Wind-mitigation features earn premium credits by law (s.627.0629 (opens in a new tab)). Homesteaded owners may qualify for a free inspection through My Safe Florida Home (opens in a new tab).
Not insurance advice. Eligibility, coverage and premiums are set by each carrier and by Citizens. Get quotes from a Florida-licensed agent and confirm the flood zone for the specific address.
Renting first
Should I Rent Before I Buy in Palm Beach County?
Many of our buyers rent first: a winter season, or a year, to learn the drive to the beach in March traffic, what August feels like, and which clubhouse they actually want to walk into. Many winter leases run January through April, and furnished homes for the season are often reserved months ahead.
We arrange the rental, and when the right home comes up we are already looking with you. How seasonal and annual rentals work here.
Search what is open now
Every luxury seasonal rental in Palm Beach County, furnished and priced by the month, live from the MLS. By town: Palm Beach · Jupiter · Palm Beach Gardens · Singer Island · West Palm Beach · Juno Beach.
A home can be committed for part of the season and still show as active, so send us your dates and we check each one with the listing agent. Leases of six months or less carry Florida sales tax and the county’s 6% tourist development tax.
Many condominiums and homeowner associations set a minimum lease term and limit how often a home can be leased each year, and some towns restrict short stays. Check the association and town rules for the specific home before you sign.
West Palm Beach averages about 66°F in January and 83°F in July, with about 62 inches of rain a year, most of it May through October (NOAA 1991-2020 normals (opens in a new tab)). Hurricane season runs June 1 to November 30 (National Hurricane Center (opens in a new tab)).
How we help
Who Helps With a Move from Chicago to Palm Beach County?
My team and I scout first: we walk the communities, read the association documents and club rules, and send you video and notes before you fly down. We coordinate with your Illinois attorney and CPA on timing, line up insurance quotes and inspections, and stay with you through closing and the homestead filing.
Questions we hear
Moving from Chicago: Questions
Where should I live in Palm Beach County if I'm moving from Chicago?
Most Chicago buyers start in Palm Beach (if you love the Gold Coast), West Palm Beach (Streeterville and the West Loop), Palm Beach Gardens (Lake Forest) or Jupiter Island (Winnetka). Illinois taxes estates above $4 million and has one of the highest property tax rates in the country; Florida has no income, estate or inheritance tax. American flies nonstop to O’Hare.
Which Palm Beach County town is most like The Gold Coast?
Palm Beach. The Gold Coast’s walkable blocks of vintage co-ops, a short walk from the lake and Oak Street, translate neatly to Palm Beach: postwar co-ops and quiet avenues on an island, with Worth Avenue for Oak Street and the Atlantic for Lake Michigan.
Which Palm Beach County town is most like Streeterville and the West Loop?
West Palm Beach. New buildings line Flagler Drive on the Intracoastal, and downtown is growing with new offices and restaurants.
Which Palm Beach County town is most like Lake Forest?
Palm Beach Gardens. Lake Forest’s old clubs and big lots point straight to Palm Beach Gardens, where private golf clubs set the rhythm of the week and the homes sit inside the gate.
Which Palm Beach County town is most like Winnetka and Kenilworth?
Jupiter Island. The quiet, leafy streets and lakefront of Winnetka have their match on Jupiter Island: estate homes between the ocean and the Intracoastal, the Jupiter Island Club and no commercial strip.
Which Palm Beach County town is most like Hinsdale and Naperville?
Jupiter. Abacoa has its own downtown, and the beach is about fifteen minutes away.
Which Palm Beach County town is most like Barrington Hills?
Wellington. Barrington Hills’ acreage and horse trails continue in Wellington, where barns, riding trails and the winter show-jumping and polo seasons are part of everyday life.
Which Palm Beach County town is most like Lake Geneva weekends?
Stuart. Lucie River, and a slower pace at the north end of the Treasure Coast.
Does Illinois have an estate tax?
Yes. Illinois taxes estates above $4,000,000, and because the $4,000,000 is a threshold rather than a credit, a taxable estate can owe on more than the amount over it. Florida has no estate tax.
Can I fly nonstop to Chicago?
Yes, to O’Hare on American, with seasonal United service. There is no nonstop to Midway from West Palm Beach.
Which town feels most like the Gold Coast?
Palm Beach: a walkable island of postwar co-ops and condominiums, Worth Avenue shopping and the ocean a block away. West Palm Beach, across the bridge, has the newer towers.
Where is the North Shore of Palm Beach County?
For Lake Forest-style club life, Palm Beach Gardens; for the quiet of Winnetka and Kenilworth, Jupiter Island and Hobe Sound.
Should I rent before I buy?
Many of our buyers rent a winter season first. Winter leases usually run January through April.
How do I establish Florida residency if I'm leaving Chicago?
Get a Florida driver license within 30 days, insure, title and register your car, register to vote at your new address, record a Declaration of Domicile with the county clerk, and file for homestead by March 1.
When is hurricane season, and how does it affect insurance?
June 1 to November 30. Insurers price wind risk by the house: roof age, opening protection and elevation. Ask for quotes and a wind mitigation inspection during the inspection period.
Is it worth moving from Chicago to Palm Beach County?
For most Illinois buyers who can make Florida their real home, yes. Florida has no state income or estate tax, Palm Beach County's median property tax rate is less than half of Illinois's, and O'Hare is about three hours nonstop; the trade is a higher insurance bill and a hot summer that is also hurricane season.
How many people move from Chicago to Palm Beach County?
724 tax returns moved from Illinois into Palm Beach and Martin counties in the 2022 to 2023 IRS migration data, most of them from Cook, Lake and DuPage counties.
Is Palm Beach County cheaper than Chicago?
On taxes, yes for most buyers: no state income or estate tax, and a median property tax rate of 0.82% in Palm Beach County against 1.88% in Illinois. Home insurance usually costs more here, and home prices vary widely by town; the towns compared shows each town's live median.
How long is the flight from Chicago to Palm Beach?
About three hours nonstop from the airport in West Palm Beach (DJT, formerly PBI) to O'Hare.
Do I need a car in Palm Beach County?
For most errands, yes. Downtown West Palm Beach and Palm Beach are walkable, and Brightline runs from West Palm Beach to Miami and Orlando, but most of the towns buyers choose here are built around driving.
Who helps people relocating from Chicago to Jupiter or Palm Beach Gardens?
Monika Phillips of Douglas Elliman Real Estate in Jupiter, licensed in Florida since 2009, works with buyers moving from Chicago, the North Shore and the western suburbs: community scouting and video before you fly down, then tours when you visit.
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Monika Phillips, Sales Associate, Douglas Elliman Real Estate
Resources
Resources and Sources
Every outside link we used to build this guide, plus the official sites you will need once you get here. Links open in a new tab.
Settling in: official Florida links
License, voting, homestead, schools and getting around.
- Florida driver license and tag for new residents (FLHSMV) (opens in a new tab)
- Register to vote in Florida (opens in a new tab)
- Homestead exemption, Palm Beach County Property Appraiser (opens in a new tab)
- Homestead exemption, Martin County Property Appraiser (opens in a new tab)
- Declaration of domicile, Palm Beach County Clerk (opens in a new tab)
- Recording, Martin County Clerk (opens in a new tab)
- School District of Palm Beach County (opens in a new tab)
- Martin County School District (opens in a new tab)
- FPL, electric service (opens in a new tab)
- Palm Beach International (DJT) nonstop routes (opens in a new tab)
- Brightline, train to Fort Lauderdale, Miami and Orlando (opens in a new tab)
Insurance, flood and storms
Check these before you make an offer.
- Citizens Property Insurance (opens in a new tab)
- My Safe Florida Home (inspections and hardening grants) (opens in a new tab)
- FEMA Flood Map Service Center (opens in a new tab)
- FloodSmart, the National Flood Insurance Program (opens in a new tab)
- Palm Beach County flood maps (opens in a new tab)
- Martin County flood zones (opens in a new tab)
- Palm Beach County Emergency Management (opens in a new tab)
- National Hurricane Center, climatology (opens in a new tab)
Taxes and residency: Chicago and Florida
The laws and rate tables behind the numbers on this page.
- Illinois Department of Revenue, income tax rates (opens in a new tab)
- Illinois Attorney General, estate tax fact sheet (opens in a new tab)
- Tax Foundation, Property Taxes by State and County, 2026 (opens in a new tab)
- Florida Constitution, Art. VII (opens in a new tab)
- Fla. Stat. s.196.031, homestead exemption (opens in a new tab)
- Fla. Stat. s.193.155, Save Our Homes and portability (opens in a new tab)
- Fla. Stat. s.193.1554, non-homestead cap (opens in a new tab)
- Florida Division of Elections, Amendment 3 (HJR 1F) (opens in a new tab)
- Fla. Stat. s.222.17, declaration of domicile (opens in a new tab)
- Fla. Stat. s.627.351, Citizens eligibility and flood requirement (opens in a new tab)
- FloodSmart (NFIP), policy terms (opens in a new tab)
- NOAA NCEI 1991-2020 normals, West Palm Beach (opens in a new tab)
News and data cited on this page
Reporting and public data behind the stories and "New" notes above.
- WLRN: Phipps Ocean Park is being rebuilt with restored dunes, 80,000 native plants, a relocated Little Red… (opens in a new tab)
- WFLX: The Nora District enters its third phase with Nora House, an 11-story building of 117 condos;… (opens in a new tab)
- Publix Corporate Newsroom: Publix opened May 21, 2026 at Avenir Town Center on Northlake Boulevard (opens in a new tab)
- TreasureCoast.com: A mixed-use project is proposed at 9025 SE Bridge Road in downtown Hobe Sound: about 4,399 sq ft of… (opens in a new tab)
- Commercial Observer: Voloridge Investment Management bought parts of Harbourside Place for $57.6 million and plans a new… (opens in a new tab)
- Commercial Observer: Related Ross bought 32 acres near State Road 7 for Village Landing, planned with a 180-room hotel and… (opens in a new tab)
- City-Data forum: Moving from Chicago to South Florida (opens in a new tab)
- Local 10 News: Citadel moves its headquarters to Miami (opens in a new tab)
Wellington photo: Pantagruel68, CC BY-SA 3.0, via Wikimedia Commons.
Tax, residency, insurance and legal information on this page is general, current as of October 2026, and is not tax, legal, insurance or financial advice. Laws and rates change. Before acting, confirm with a licensed CPA, an attorney licensed in Florida and in your current state, and a Florida-licensed insurance agent. Links to outside sites are for convenience; we do not control or endorse them. Restaurant, club and brand names belong to their owners and imply no affiliation. Listing counts are live from BeachesMLS, change throughout the day, include only listings available for internet display, and are deemed reliable but not guaranteed. All material presented herein is intended for information purposes only. While this information is believed to be correct; it is represented subject to errors, omission, changes, or withdrawal without notice. All property information, including, but not limited to square footage, room count, number of bedrooms and the school district in property listings are deemed reliable, but should be verified by the Agent’s own attorney, architect, or zoning expert. Monika Phillips, Sales Associate, Douglas Elliman Real Estate, 400 South US Highway 1, Suite C1, Jupiter, FL 33477. © 2026 Douglas Elliman Real Estate. All material presented herein is intended for information purposes only. While this information is believed to be correct, it is represented subject to errors, omissions, changes or withdrawal without notice. Equal Housing Opportunity.
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