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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Wrigleyville
Dream Condo steps from Wrigley Field!
2 bedrooms, 2 beds, 1 private bathroom
6–11 Jul
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4.82 out of 5 average rating, 387 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
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
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
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
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
9–14 Aug
New place to stay
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Apartment in Wicker Park
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds
5–10 Jul
New place to stay
Guest house in West Town
Upscale Wicker Park Retreat
4 bedrooms, 8 beds
12–17 Jul
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
5–10 Jul
4.99 out of 5 average rating, 346 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
4–9 Aug
4.95 out of 5 average rating, 21 reviews
Superhost
Flat in South Loop
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 101 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 160 reviews