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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest house in Chicago
Pro Cleaned & Isolated West Loop Coach House
1 bedroom, 2 beds, 1 private bathroom
9–14 Aug
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4.87 out of 5 average rating, 492 reviews
Top guest favourite
Flat in Chicago
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
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds, 6 bathrooms
29 Aug – 3 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
4.92 out of 5 average rating, 189 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
4.95 out of 5 average rating, 41 reviews
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Chicago
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 reviews
Guest favourite
Flat in Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms, 3 double beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 9 reviews
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 233 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
4.9 out of 5 average rating, 119 reviews