filters

Search results; Over 1,000 homes in Chicago

Superhost
Boutique hotel in The Loop
Private King Room in Theatre District
1 bedroom, 1 bed, 1 private bathroom
25–30 Sept
,
4.79 out of 5 average rating, 19 reviews
Flat in West Side
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
19–24 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 36 reviews
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Top guest favourite
Flat in South Side
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Bridgeport
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 23 reviews
Room in The Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
9–14 Sept
4.33 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Bronzeville
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds, 6 bathrooms
20–25 Sept
4.8 out of 5 average rating, 10 reviews
Flat in West Side
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Little Italy
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds, 3 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Wicker Park
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds, 3.5 bathrooms
24–29 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 70 reviews
Flat in Downtown Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 39 reviews
Flat in West Side
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
New place to stay