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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Rogers Park Township
Your Chicago Retreat
3 bedrooms, 3 beds, 1.5 private bathrooms
9–14 Aug
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4.99 out of 5 average rating, 300 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
27 Sept – 2 Oct
4.9 out of 5 average rating, 60 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
7–12 Sept
4.96 out of 5 average rating, 26 reviews
Guest favourite
Room in Irving Park
Lovely Front Room #1 in a New Renovated Apartment
2 single beds
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Guest suite in Logan Square
2BR/1.5 Bath in Logan Square
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.95 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
14–19 Sept
4.97 out of 5 average rating, 65 reviews
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
23–28 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in West Side
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Apartment in Lake View
Bright, new 2BR in the heart of East Lakeview
2 bedrooms, 3 beds
7–12 Sept
4.99 out of 5 average rating, 130 reviews
Guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
9–14 Aug
4.93 out of 5 average rating, 235 reviews
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Ukrainian Village
Vintage Ukrainian Village Apartment
2 bedrooms, 2 double beds
17–22 Aug
4.95 out of 5 average rating, 186 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews