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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Urban Chic Apartment by the Magnificent Mile
2 bedrooms, 2 beds, 1 private bathroom
26–31 Oct
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4.94 out of 5 average rating, 289 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
12–17 Oct
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom, 1 king bed
25–30 Oct
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
16–21 Aug
4.97 out of 5 average rating, 64 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
5–10 Jul
4.88 out of 5 average rating, 474 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed
21–26 Sept
4.96 out of 5 average rating, 113 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 184 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
1–6 Nov
4.96 out of 5 average rating, 309 reviews
Guest favourite
Rooms in Oak Park
Single bedroom with Asian decor in family home
2 bedrooms, 1 double bed
17–22 Aug
4.94 out of 5 average rating, 381 reviews
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest suite in Chicago
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 Chicago
Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown
1 bedroom, 2 beds
21–26 Sept
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Room in Chicago
Al's Oasis Chicago
1 queen bed
5–10 Jul
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed
5–10 Jul
4.94 out of 5 average rating, 140 reviews
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds
27 Sept – 2 Oct
New place to stay
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
5–10 Jul
4.93 out of 5 average rating, 336 reviews