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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5 beds
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
3 beds
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
3 beds
16–21 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 beds
7–12 Sept
4.94 out of 5 average rating, 141 reviews
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
3 beds
18–23 Aug
4.94 out of 5 average rating, 66 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Room in Chicago
Stay with Charles
Historic North Park home
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
3 queen beds
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Guest favourite
Flat in Chicago
Cozy Urban View Retreat Near Downtown - Sleeps 7
4 beds
18–23 Aug
4.71 out of 5 average rating, 7 reviews
Superhost
Home in Chicago
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
11 beds
26–31 Jul
Top guest favourite
Townhouse in Oak Park
A Pleasant Stay in Oak Park
2 beds
9–14 Nov
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Superhost
Flat in Chicago
Luxe 4BR Brick & Stone by Douglass Park + Med Dist
4 beds
19–24 Jul
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 queen bed
22–27 Jul
4.97 out of 5 average rating, 93 reviews
Guest favourite
Flat in Chicago
Cozy Apt+Steps to Train+10 mins to Downtown
2 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 46 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 double beds
9–14 Aug
4.93 out of 5 average rating, 236 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
3 beds
23–28 Aug
5.0 out of 5 average rating, 12 reviews