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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in West Town
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 private bathrooms
10–15 Aug
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5.0 out of 5 average rating, 59 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Flat in West Side
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
4.88 out of 5 average rating, 476 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 53 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
4.91 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Oct
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 567 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
14–19 Aug
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 160 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Superhost
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
4.9 out of 5 average rating, 119 reviews, 3 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
Guest favourite
Flat in Chicago Loop
Spacious 1-bedroom South Loop Loft I Sleep 5
4.94 out of 5 average rating, 232 reviews, 1 bedroom, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Albany Park
NorthSide Chicago duplex 5-BD,2King size-free park
4.97 out of 5 average rating, 198 reviews, 5 bedrooms, 6 beds, 2 bathrooms
8–13 Nov
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
4.97 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept