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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Studio 15 Minutes From Ohare!
Studio, 1 bed, 1 private bathroom
23–28 Aug
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4.97 out of 5 average rating, 203 reviews
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, 108 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
16–21 Aug
New place to stay
Home in Chicago
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
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
Guest favourite
Flat in Chicago
Downtown Penthouse Huge Patio with Great View
3 bedrooms, 5 beds
9–14 Aug
4.99 out of 5 average rating, 78 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
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
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
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
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
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
11–16 Sept
4.95 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
22–27 Aug
5.0 out of 5 average rating, 21 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
Great place in the Heart of Pilsen
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 27 reviews