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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
21–26 Aug
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4.96 out of 5 average rating, 158 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
5–10 Jul
4.93 out of 5 average rating, 336 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
26–31 Jul
5.0 out of 5 average rating, 9 reviews
Flat in Chicago
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds
26–31 Jul
New place to stay
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
4–9 Sept
New place to stay
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed
23–28 Oct
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
21–26 Sept
4.99 out of 5 average rating, 124 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
New place to stay
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Jul
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 110 reviews
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Superhost
Home in Schaumburg
Chicagoland-Schaumburg/ORD 3BR Ranch Home, sleeps7
3 bedrooms, 4 beds
26–31 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms, 3 beds
26–31 Jul
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews