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Search results; Over 1,000 homes in Chicago

Guest favorite
Home in West Side
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 private bath
Oct 4 – 9
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4.94 out of 5 average rating, 147 reviews
Guest favorite
Apartment in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
Aug 16 – 21
4.9 out of 5 average rating, 126 reviews
Top guest favorite
Condo in West Town
Great location. Free parking.
1 bedroom, 1 queen bed
Nov 1 – 6
4.97 out of 5 average rating, 917 reviews
Superhost
Condo in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
Oct 18 – 23
Guest favorite
Apartment in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
Dec 27 – Jan 1
4.95 out of 5 average rating, 127 reviews
Top guest favorite
Apartment in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
Aug 17 – 22
5.0 out of 5 average rating, 11 reviews
Top guest favorite
Guesthouse in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds
Sep 27 – Oct 2
5.0 out of 5 average rating, 22 reviews
Room in Bridgeport
Bridgeport Chicago near everything affordable.-5
1 double bed
Aug 22 – 27
New place to stay
Guest favorite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
Sep 28 – Oct 3
4.95 out of 5 average rating, 20 reviews
Top guest favorite
Condo in Lincoln Park
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
Nov 29 – Dec 4
4.99 out of 5 average rating, 169 reviews
Top guest favorite
Apartment in Lake View
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds
Aug 23 – 28
4.95 out of 5 average rating, 269 reviews
Guest favorite
Apartment in Wicker Park
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
Aug 28 – Sep 2
5.0 out of 5 average rating, 6 reviews
Guest favorite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
Aug 30 – Sep 4
4.88 out of 5 average rating, 441 reviews
Top guest favorite
Apartment in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
Nov 1 – 6
4.97 out of 5 average rating, 35 reviews
Top guest favorite
Condo in West Town
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds
Aug 20 – 25
5.0 out of 5 average rating, 65 reviews
Superhost
Apartment in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
Sep 23 – 28
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
Nov 1 – 6
4.9 out of 5 average rating, 122 reviews
Guest favorite
Apartment in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
Aug 15 – 20
4.87 out of 5 average rating, 15 reviews
Guest favorite
Apartment in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
Sep 27 – Oct 2
4.96 out of 5 average rating, 70 reviews