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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
iKlektik House Chicago/BlueJay
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
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4.92 out of 5 average rating, 258 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Jul
Superhost
Home in Chicago
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
6 bedrooms, 11 beds, 3 bathrooms
26–31 Jul
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
4.88 out of 5 average rating, 434 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Chicago
Big house in the BEST Location!
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Sept
Place to stay in Chicago
Guest room in Dunning, Chicago IL
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Sept
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 48 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct
Top guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Superhost
Flat in Chicago
Renovated 2BR in Prime L. | Sleeps 6 |Pet Friendly
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul