Explore Chicago

Where to stay

PLUS
  1. Entire loft
  2. Forest Park
Walk to Oak Park from a Bright Madison Street Loft
$122 per night
  1. Hotel room
  2. Near North Side
Traveler's Dream - 1 bed in a shared bedroom
$46 per night
  1. Entire rental unit
  2. Near North Side
Kasa Chicago 🛍 Family Travel Ready, In Unit W/D + Fast WiFi 🛍 River North
$241 per night
PLUS
  1. Entire guesthouse
  2. Humboldt Park
Unwind in the Bath at a Hip, Historic Coach House
$125 per night
SUPERHOST
  1. Entire rental unit
  2. Ukrainian Village
#1 neighborhood in Chicago w/ private balcony
$79 per night
  1. Entire rental unit
  2. Near West Side
*The Oakley-Modern 3br Duplex 12 mins to Downtown
$209 per night
  1. Room in boutique hotel
  2. Loop
Staypineapple Chicago, Deluxe King
$119 per night
  1. Entire loft
  2. Lakeview
Grand Studio in the Heart of Lakeview!
$61 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Lakeview
Urban Comfort in the Heart of Chicago
$20 per night
SUPERHOST
  1. Private room
  2. Ukrainian Village
Stylish & Ample 1PBR STAYCATION SPACE For You
$24 per night

Popular experiences

Book activities led by local hosts on your next trip
Chicago
Gangsters and Ghosts Tours
From Price:$27 / person
Chicago
Sail Chicago's Lakefront on a Yacht
From Price:$150 / person
Chicago
Spray 'n' Sip- Graffiti/Aerosol Workshop
From Price:$40 / person
Chicago
Chicago Art Institute Skip the Line Tour
From Price:$94 / person
Chicago
Bikes, Bites & Brews-Signature Bike Tour
From Price:$85 / person
Chicago
Chicago Food and Architecture Experience
From Previous price:$80Discounted price:$64 / person
Chicago
Amazing photo shoot in Chicago
From Price:$125 / person
Chicago
Glassblowing in an artist studio
From Previous price:$70Discounted price:$56 / person
Chicago
MUST HAVE CHICAGO PHOTOS- OUTDOORS
From Price:$98 / person
Chicago
Chicago's Underground Donut Tour
From Price:$30 / person

Stay with a Superhost

Make yourself at home with these experienced hosts.
PLUS
  1. Entire loft
  2. Forest Park
Walk to Oak Park from a Bright Madison Street Loft
$122 per night
PLUS
  1. Entire guesthouse
  2. Humboldt Park
Unwind in the Bath at a Hip, Historic Coach House
$125 per night
SUPERHOST
  1. Entire rental unit
  2. Ukrainian Village
#1 neighborhood in Chicago w/ private balcony
$79 per night
PLUS
  1. Entire rental unit
  2. Evanston
Charming, Sunny Apartment with Backyard Garden
$124 per night
SUPERHOST
  1. Private room
  2. Berkeley
Gypsy's Hideaway
$94 per night
SUPERHOST
  1. Entire rental unit
  2. Forest Park
Train ride to Chicago, welcome home
$89 per night
SUPERHOST
  1. Entire rental unit
  2. Frank Lloyd Wright District
Long stays welcome@warm&cute vintage 2BR
$123 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Lakeview
Urban Comfort in the Heart of Chicago
$20 per night
SUPERHOST
  1. Private room
  2. Ukrainian Village
Stylish & Ample 1PBR STAYCATION SPACE For You
$24 per night
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Charming Private Room in Wicker Park
$29 per night

Food tour experiences

Discover local eateries and sample distinct dishes.
Chicago
Underground Donut Tour - West Loop
From Price:$30 / person
Chicago
PAELLA & FIDEUA small or private class
From Price:$79 / person
Chicago
West Side Foodie Ride Bike Tour
From Price:$80 / person
Chicago
River North Food Tour
From Price:$75 / person
Chicago
West Loop Pizza Crawl
From Price:$55 / person
Chicago
Chicago Food Tour in River North
From Price:$48 / person
Chicago
MOLE from scratch, small o private class
From Price:$78 / person
Chicago
Chicago Food Tour: Saigon to Stockholm
From Price:$75 / person
Chicago
A Night of Traditional Italian Cuisine
From Price:$80 / person
Chicago
Chicago Favorites Food Walking Tour
From Price:$63 / person

Architecture experiences

Chicago
All-Weather Architecture & History Trek
From Price:$29 / person
Chicago
Night Crimes Tour
From Price:$50 / person
Chicago
Chicago History & Highlights Tour
From Price:$40 / person
Oak Park
Oak Park Walking Architecture Tour
From Price:$15 / person
Chicago
Chicago Crime Tour
From Price:$45 / person
Chicago
Explore Dazzling Architecture Interiors
From Price:$30 / person
Chicago
Urban Planning Excursion with Emily
From Price:$58 / person
Chicago
Chicago Pop Culture Walking Tour
From Price:$25 / person
Chicago
Discover River North and Chinatown by L
From Price:$33 / person
Chicago
Nighttime Photo Journey
From Price:$125 / person