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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
4 bedrooms, 7 beds, 3 private bathrooms
7–12 Aug
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4.92 out of 5 average rating, 196 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
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
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
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
15–20 Aug
New place to stay
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 122 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
16–21 Aug
Guest favourite
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
1 bedroom, 1 queen bed
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
20–25 Sept
4.95 out of 5 average rating, 19 reviews
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
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
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
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
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
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
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
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