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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
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 Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
New place to stay, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Guest favourite
Flat in Downtown Chicago
Modern 3BR Apartment Near North Ave Shops
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 bathrooms
5–10 Jul
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Top guest favourite
Flat in Ukrainian Village
Stylish & Spacious Multi-Level Apt in Wicker Park
4.96 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 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
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 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
Guest favourite
Home in Wrigleyville
*New* Luxury Wrigley Penthouse, Free Parking
4.92 out of 5 average rating, 50 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
5–10 Jul
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
4.88 out of 5 average rating, 433 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
4.97 out of 5 average rating, 155 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
Guest favourite
Flat in West Side
Cozy Urban View Retreat Near Downtown - Sleeps 7
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 1 bathroom
13–18 Aug