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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Chicago
Huge Downtown Gem *Yard *Parking *Fireplace
5 bedrooms, 8 beds, 3.5 private bathrooms
30 Aug – 4 Sept
,
4.88 out of 5 average rating, 161 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.92 out of 5 average rating, 26 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 106 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 84 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, 22 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Dec
4.95 out of 5 average rating, 126 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
New place to stay
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 56 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
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.67 out of 5 average rating, 3 reviews
Guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 187 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed, 1 bathroom
10–15 Nov
4.96 out of 5 average rating, 317 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.99 out of 5 average rating, 108 reviews
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
Top guest favourite
Flat in Chicago
Fulton House #1 (2bd/ 1ba)
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.95 out of 5 average rating, 112 reviews