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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
East Lakeview Designer Condo with 2 Bd, 2 Bath
2 bedrooms, 3 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.96 out of 5 average rating, 158 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
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
15–20 Jul
4.97 out of 5 average rating, 89 reviews
Place to stay in Chicago
Self check in 24h near downtown Chicago p2
1 bedroom, 1 queen bed
15–20 Aug
New place to stay
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
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 119 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, 9 reviews
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed
31 Aug – 5 Sept
New place to stay
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds
17–22 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, 64 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
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
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
1 bedroom, 1 king bed
17–22 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen 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
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
13–18 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds
11–16 Jul
4.98 out of 5 average rating, 40 reviews