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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Roscoe Village
The Roscoe Village Guesthouse
2 bedrooms, 2 beds, 1 private bathroom
2–7 Aug
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4.91 out of 5 average rating, 205 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
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
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
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
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
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 53 reviews
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
6–11 Jul
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
14–19 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Logan Square
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds
12–17 Jul
4.98 out of 5 average rating, 156 reviews
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed
23–28 Oct
4.91 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago Loop
Spacious 1-bedroom South Loop Loft I Sleep 5
1 bedroom, 4 beds
9–14 Aug
4.94 out of 5 average rating, 232 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, 11 reviews
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds
6–11 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds
9–14 Aug
4.77 out of 5 average rating, 567 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, 160 reviews
Superhost
Home in Downtown Chicago
Gold Coast Home|Rooftop |PoolTable |Parking |Views
4 bedrooms, 6 beds
6–11 Jul
4.89 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Albany Park
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds
8–13 Nov
4.97 out of 5 average rating, 198 reviews