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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Logan Square
Luxe, Private Suite w/Own Entrance-2023 Renovated
1 bedroom, 1 bed, 1 private bathroom
5–10 Jul
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4.94 out of 5 average rating, 430 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
7–12 Jul
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Downtown Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms, 3 double beds, 2 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
4.95 out of 5 average rating, 107 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Superhost
Flat in Downtown Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
New place to stay
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
4–9 Aug
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Apartment in Wicker Park
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds, 3 bathrooms
5–10 Jul
New place to stay
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Flat in South Loop
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 346 reviews