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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
The South Loop Reserve I Sleep 6 I Top Rated
2 bedrooms, 2 beds, 2 private bathrooms
3–9 Aug
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4.93 out of 5 average rating, 259 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
4.92 out of 5 average rating, 520 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
4.95 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Oct
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 312 reviews, 1 queen bed, 1 bathroom
1–6 Nov
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Chicago
Spacious 1-bedroom South Loop Loft I Sleep 5
4.94 out of 5 average rating, 232 reviews, 1 bedroom, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Flat in Chicago
Modern & Spacious Condo Minutes from the Loop
4.97 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Guest favourite
Flat in Chicago
Modern 2 Bedroom in West Town With Garage Parking
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
14–19 Aug
Top guest favourite
Rooms in Oak Park
Single bedroom with Asian decor in family home
4.94 out of 5 average rating, 383 reviews, 2 bedrooms, 1 double bed, 1 bathroom
17–22 Aug
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Guest favourite
Flat in Chicago
iKlektik House Chicago/Cardinal
4.91 out of 5 average rating, 487 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 83 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
4.96 out of 5 average rating, 586 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Nov