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Search results; Over 1,000 homes in Chicago

Guest favourite
Boutique hotel in Chicago
Spacious Hotel Room in The Loop
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.81 out of 5 average rating, 243 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
4.92 out of 5 average rating, 59 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 120 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
4.98 out of 5 average rating, 617 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 300 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
5.0 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
4.97 out of 5 average rating, 161 reviews, 2 bedrooms, 4 beds, 2 bathrooms
14–19 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
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 568 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Room in Chicago
Lovely Front Room #1 in a New Renovated Apartment
4.91 out of 5 average rating, 103 reviews, 2 single beds, 1 bathroom
22–27 Sept
Top guest favourite
Apartment in Chicago
Bright, new 2BR in the heart of East Lakeview
4.99 out of 5 average rating, 130 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
4.9 out of 5 average rating, 504 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 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