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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Whole Flat in Private Club. Walk to L, Dining & Shows
1 bedroom, 1 bed, 1 shared bathroom
16–21 Aug
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4.9 out of 5 average rating, 597 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
7–12 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 126 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds
17–22 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
4–9 Aug
4.94 out of 5 average rating, 109 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds
19–24 Oct
4.98 out of 5 average rating, 108 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Flat in Chicago
Gym + Workspace • Sleeps 8 • Near O’Hare
3 bedrooms, 3 queen beds
9–14 Aug
New place to stay
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Flat in Chicago
Zen City Escape | Patio + Free Parking
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 25 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Guest favourite
Room in Chicago
x3 Private room with bath Hyde Park UChicago
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 19 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Top guest favourite
Flat in Chicago
An elegant Chicago Northside Getaway
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 374 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
24–29 Oct
4.9 out of 5 average rating, 49 reviews