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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
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 48 reviews
Flat in West Side
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed, 1 bathroom
23–28 Oct
4.91 out of 5 average rating, 22 reviews
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.94 out of 5 average rating, 66 reviews
Guest favourite
Flat in Chicago Loop
Spacious 1-bedroom South Loop Loft I Sleep 5
1 bedroom, 4 beds, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 232 reviews
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.77 out of 5 average rating, 567 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Logan Square
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 156 reviews
Guest favourite
Flat in West Town
Modern 2 Bedroom in West Town With Garage Parking
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Chicago Loop
Comfy 2BR-2BTH | Steps to The Bean & Michigan Ave
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.94 out of 5 average rating, 140 reviews
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 160 reviews
Top guest favourite
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 12 reviews