Moving from Orlando to Chicago

The Story

Orlando-to-Chicago is hospitality → Fortune 500 corporate move. FL 0% → IL 4.95% costs $4,950+/yr. Housing 3% cheaper, COL 8% higher. Pull: Fortune 500 HQs (United Airlines, Boeing, Abbott, McDonald's, Walgreens, Hyatt, Hilton corporate), Big Ten + UChicago + Northwestern, CME quant, Lake Michigan, deep-dish.

Why This Move

Why people move from Orlando to Chicago.

Fortune 500 HQs — United, Boeing, Abbott, McDonald's, Walgreens, Hyatt
Hospitality corporate — Hyatt, Hilton, Marriott offices (Orlando hospitality bridge)
Big Ten + UChicago + Northwestern research
CME/CBOT futures + Citadel quant
Lake Michigan + 26 miles of beach
Deep-dish, hot dogs, rich food culture
Walkable urban + L transit
Slightly cheaper housing

Cost Comparison

The money side of FL → IL.

Orlando

Median home$370,000
Income tax0% (FL)
Cost index99

Chicago

Median home$360,000
Income tax4.95% (IL flat)
Cost index107

What to Do in Chicago

Things you'll want to know about your new city.

Bookmark this page — these are the icons of Chicago, organized by what kind of day you're planning.

Outdoors & Recreation

Millennium Park (Cloud Gate / 'The Bean') — Anish Kapoor's sculpture; Pritzker Pavilion concerts
Willis (Sears) Tower Skydeck — 103rd floor with glass-floor 'Ledge'
Chicago Riverwalk — 1.25-mile waterfront walk with bars and architecture views
Lake Michigan Lakefront Trail — 18-mile beach/path along the lake

Culture & Arts

Art Institute of Chicago — Among top 10 art museums globally; Hopper, Picasso, Wood
Wrigley Field — 1914 stadium; Cubs games, ivy walls, rooftop bleachers
Architecture Boat Tour — Chicago Architecture Center's tour — best way to see the city

Family-Friendly

Navy Pier — Ferris wheel, IMAX, Children's Museum, fireworks
Field Museum of Natural History — SUE the T. rex; Egyptian mummies; gem hall
Lincoln Park Zoo — Free zoo in Lincoln Park since 1868

Where to Eat

Chicago's essential restaurants.

The dining list every Chicago resident knows by heart. Save the spots, work through them.

Alinea Modernist fine dining Lincoln Park

Three Michelin stars; Grant Achatz
Lou Malnati's Pizzeria Deep dish pizza Multiple

Classic Chicago deep-dish
Au Cheval American/burger West Loop

The cheeseburger of the decade
Smoque BBQ BBQ Old Irving Park

Texas-style brisket and ribs
Girl & The Goat New American Fulton Market

Stephanie Izard's flagship; Top Chef winner
Pequod's Pizza Deep dish pizza Lincoln Park / Morton Grove

Caramelized cheese crust
Lula Cafe Farm-to-table Logan Square

Seasonal menus, beloved brunch
Topolobampo Mexican fine dining River North

Rick Bayless's regional Mexican

Where to Live

Best Chicago neighborhoods for Orlando transplants.

Mapped to the Orlando neighborhoods that probably feel like home to you.

West Loop

If Thornton Park was your scene — walkable urban, restaurants
Wicker Park

If College Park was your vibe — artsy, walkable
Lincoln Park

If Winter Park was your goal — affluent, walkable, top schools
Naperville (suburb)

If Lake Nona was your model — master-planned, top schools
Oak Park (suburb)

If Baldwin Park was your scene — charming, walkable
Evanston (suburb)

If you wanted university — Northwestern, lakefront

Climate & Walkability

What daily life feels like in Chicago.

Climate

Continental — four extreme seasons. Hot, humid summers (75-90°F). Brutal winters with windchill (-10 to 30°F, lake-effect snow). Spring is muddy; fall is glorious. 'Windy City' nickname earned. 189 sun days/year.

Summer70-85°F
Winter21-35°F
Sun days/yr189
Rainfall37 inches

Walkability

Walk Score77/100
Transit Score65/100
Bike Score72/100

Chicago is very walkable — daily errands rarely require a car.

Outdoors & Recreation

Lakefront Trail — 18 miles of beach/path along Lake Michigan
Chicago Riverwalk — kayaking, paddleboarding, riverboats
Lincoln Park / Grant Park / Millennium Park — major urban parks
Indiana Dunes National Park (1 hr east) — beaches and trails
Starved Rock State Park (1.5 hrs west) — canyons and waterfalls
Biking — among most bike-friendly major US cities, Divvy bike share

Reality Check

What changes about your daily life.

FL 0% becomes IL 4.95% — costs $4,950+/year on $100K
Housing 3% cheaper — $370K Orlando becomes $360K Chicago
COL 8% higher
Climate flips humid subtropical to humid continental — real winters (-10°F)
Property tax IL 2.1% high vs FL 0.9%
Car → L/Metra transit major upgrade
Disney/Universal hospitality → Hyatt/Hilton/United corporate
Sports — gain Cubs/Bears/Bulls/Blackhawks, lose Magic

Driving Routes

How to drive there.

I-75 N to I-65 N

1,170 miles via Atlanta, Nashville, Indianapolis. 18 hours / 2 days.

Move Logistics

What it takes to move 1,170 miles.

Full-service (3BR)$5,800-$10,500
Container/PODS$4,000-$6,500
DIY (26-ft truck)$3,000-$5,200
Best monthsApr-Oct (avoid winter)
Lead time8-10 weeks ahead

USDOT-registered.

Common Questions