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Search results; Over 1,000 homes in Chicago

Superhost
Apartment in West Side
The Upscale Getaway Near Downtown
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Oct
,
4.93 out of 5 average rating, 296 reviews
Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
1–6 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
20–25 Aug
4.89 out of 5 average rating, 134 reviews
Room in Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
23–28 Aug
New place to stay
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
19–24 Aug
New place to stay
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
27 Oct – 1 Nov
4.95 out of 5 average rating, 166 reviews
Top guest favourite
Flat in Lake View
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds
23–28 Aug
4.95 out of 5 average rating, 269 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
26–31 Oct
4.91 out of 5 average rating, 70 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 37 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 109 reviews
Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 256 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Downtown Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
6 bedrooms, 15 beds
1–6 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Bridgeport
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 30 reviews
Flat in Wrigleyville
2,400 SF 4BR + 2 Parking | Steps to Wrigley
4 bedrooms, 6 beds
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 reviews