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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Chicago
BnB on Grace Street - Modern 2-Bedroom Guest Suite
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.93 out of 5 average rating, 231 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Flat in Chicago
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 Chicago
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
Top 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
16–21 Aug
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
4.8 out of 5 average rating, 10 reviews, 9 bedrooms, 15 beds, 6 bathrooms
29 Aug – 3 Sept
Top guest favourite
Flat in Chicago
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
Flat in Chicago
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Guest favourite
Flat in Chicago
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
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
Guest favourite
Flat in Chicago
Modern 3BR Apartment Near North Ave Shops
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
4.92 out of 5 average rating, 189 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 234 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Flat in Chicago
2BR/1BA Apt w/ Modern Amenities Rogers Park
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul