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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
The Grand Kimball Lodge, Logan Square, Sleeps 15
4 bedrooms, 10 beds, 3 private bathrooms
30 Sept – 5 Oct
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4.96 out of 5 average rating, 173 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Flat in Chicago
Stylish Flat near Downtown,Obama Library, UChicago
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Sept
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
New place to stay
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
26–31 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Room in Chicago
Room w/ Private Bath | Chicago IL
1 queen bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
4.91 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 30 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
6–11 Aug
4.91 out of 5 average rating, 117 reviews