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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 beds, 1 private bathroom
23–28 Nov
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4.99 out of 5 average rating, 953 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
7–12 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, 126 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
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
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
4.94 out of 5 average rating, 109 reviews
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, 3 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, 23 reviews
Flat in Chicago
Gym + Workspace • Sleeps 8 • Near O’Hare
3 bedrooms, 3 queen beds, 2 bathrooms
9–14 Aug
New place to stay
Superhost
Flat in Chicago
Modern 2BR in Lincoln Park | Walk to everywhere
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Aug
Guest favourite
Flat in Chicago
Downtown Penthouse Huge Patio with Great View
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 78 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 108 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
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Chicago
Zen City Escape | Patio + Free Parking
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 25 reviews