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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Newly Renovated, Spacious 2BR in Andersonville
2 bedrooms, 3 beds, 1 private bathroom
30 Oct – 4 Nov
,
4.98 out of 5 average rating, 169 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
16–21 Jul
4.97 out of 5 average rating, 92 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 65 reviews
Superhost
Flat in Chicago
Renovated 2BR in Prime L. | Sleeps 6 |Pet Friendly
2 bedrooms, 3 beds
20–25 Jul
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
23–28 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3 bedrooms, 3 queen beds
9–14 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
4.7 out of 5 average rating, 10 reviews
Place to stay in Chicago
J33. Next to downtown private room in shared apt
1 bedroom, 1 bed
19–24 Jul
New place to stay
Top guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews