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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.88 out of 5 average rating, 477 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
4.91 out of 5 average rating, 58 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
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
12–17 Oct
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
Room in Chicago
Lovely Front Room 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, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
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
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
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 349 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
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
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
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
4.98 out of 5 average rating, 187 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
Top 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 Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Prime Logan Square apartment
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest suite in Chicago
Private Lincoln Square Garden Apt
4.92 out of 5 average rating, 490 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Nov
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept