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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Whole Flat in Private Club. Walk to L, Dining & Shows
1 bedroom, 1 bed, 1 shared bathroom
10–15 Aug
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4.91 out of 5 average rating, 591 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 81 reviews
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
3 bedrooms, 3 beds, 2 bathrooms
4–9 Jul
New place to stay
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
4.95 out of 5 average rating, 107 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
New place to stay
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds, 1 bathroom
4–9 Jul
New place to stay
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 64 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Place to stay in Chicago
The Native Garden at the City's Edge
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
4–9 Jul
4.95 out of 5 average rating, 41 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Apartment in Chicago
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 101 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews