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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
16–21 Aug
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4.97 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 913 reviews
Top guest favourite
Apartment in Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Nov
4.97 out of 5 average rating, 35 reviews
Guest favourite
Room in Chicago
Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan
1 queen bed, 1.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 52 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 69 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.95 out of 5 average rating, 164 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 440 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds, 2.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 91 reviews
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 147 reviews
Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
4.96 out of 5 average rating, 594 reviews
Top guest favourite
Flat in Chicago
Zen City Escape | Patio + Free Parking
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Chicago
Downtown Penthouse Huge Patio with Great View
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 79 reviews