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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
The Urban Oasis | Outdoor Lounge • Sleeps 10+
4 bedrooms, 7 beds, 2.5 private bathrooms
26–31 Jul
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4.93 out of 5 average rating, 169 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
15–20 Nov
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
23–28 Jul
4.97 out of 5 average rating, 96 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 121 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
15–20 Aug
New place to stay
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, 13 reviews
Place to stay in Chicago
Self check in 24h near downtown Chicago p2
1 bedroom, 1 queen bed
13–18 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
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
19–24 Jul
New place to stay
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds
10–15 Aug
4.94 out of 5 average rating, 16 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, 16 reviews
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
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
Flat in Chicago
Apartment near McCormick w/ gym & workspace
1 bedroom, 2 beds
15–20 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
The Nest | Luxe Garden Unit Near Downtown
2 bedrooms, 2 beds
10–15 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 67 reviews