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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Wicker Park
Fantastic Home in Wicker Park
5 bedrooms, 11 beds, 6 private bathrooms
8–13 Aug
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4.99 out of 5 average rating, 153 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Superhost
Flat in West Town
Luxury Penthouse Collection PH1 - Fulton Market
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
New place to stay
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Nov
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 913 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 15 reviews
Hotel room in Downtown Chicago
Unwind in River North! 3 Family-friendly Units!
3 bedrooms, 6 double beds, 3 bathrooms
16–21 Aug
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 440 reviews
Top guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
4.96 out of 5 average rating, 594 reviews
Top guest favourite
Flat in Bridgeport
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Superhost
Flat in Wicker Park
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Portage Park
Sleeps 15 • Game Room • Theater • Gym
7 bedrooms, 8 beds, 3 bathrooms
8–13 Aug
New place to stay
Superhost
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Superhost
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 30 reviews