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Search results; Over 1,000 homes in Chicago

Top guest favorite
Guesthouse in Chicago
Charming private coach house
1 bedroom, 2 beds, 1 private bath
Sep 23 – 28
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4.97 out of 5 average rating, 62 reviews
Guest favorite
Apartment in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bath
Aug 12 – 17
4.9 out of 5 average rating, 126 reviews
Guest favorite
Apartment in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
4.87 out of 5 average rating, 15 reviews
Top guest favorite
Guesthouse in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bath
Sep 27 – Oct 2
5.0 out of 5 average rating, 22 reviews
Apartment in Cicero
Apartment in Cicero
3 bedrooms, 3 beds, 1 bath
Aug 16 – 21
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Apartment in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 baths
Aug 17 – 22
5.0 out of 5 average rating, 11 reviews
Guest favorite
Apartment in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 baths
Dec 27 – Jan 1
4.95 out of 5 average rating, 127 reviews
Top guest favorite
Apartment in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
4.97 out of 5 average rating, 34 reviews
Top guest favorite
Condo in Chicago
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 baths
Aug 20 – 25
5.0 out of 5 average rating, 65 reviews
Top guest favorite
Apartment in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bath
Sep 27 – Oct 2
4.99 out of 5 average rating, 359 reviews
Top guest favorite
Condo in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bath
Nov 29 – Dec 4
4.99 out of 5 average rating, 169 reviews
Place to stay in Chicago
Charming Room in Historic Ukrainian Village!
1 bedroom, 1 queen bed, 1 bath
Sep 6 – 11
New place to stay
Top guest favorite
Apartment in Chicago
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed, 1 bath
Nov 30 – Dec 5
5.0 out of 5 average rating, 318 reviews
Guest favorite
Apartment in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 baths
Sep 27 – Oct 2
4.96 out of 5 average rating, 70 reviews
Top guest favorite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bath
Nov 11 – 16
4.96 out of 5 average rating, 309 reviews
Top guest favorite
Apartment in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
4.95 out of 5 average rating, 269 reviews
Guest favorite
Apartment in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 baths
Aug 30 – Sep 4
4.96 out of 5 average rating, 24 reviews
Top guest favorite
Apartment in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
5.0 out of 5 average rating, 17 reviews
Guest favorite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
4.88 out of 5 average rating, 441 reviews