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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 bed, 1 private bathroom
1–6 Nov
,
4.97 out of 5 average rating, 915 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
Guest favourite
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, 7 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 16 reviews
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
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 359 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 3 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
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
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
2–7 Nov
4.95 out of 5 average rating, 165 reviews
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.91 out of 5 average rating, 118 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Flat in Chicago
Zen City Escape | Patio + Free Parking
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Flat in Chicago
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
New place to stay
Superhost
Flat in Chicago
Modern Gateway in Lincoln Park | Parking |Sleeps 6
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 5 reviews