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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Urban Chic Apartment by the Magnificent Mile
2 bedrooms, 2 beds, 1 private bathroom
26–31 Oct
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4.94 out of 5 average rating, 289 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 77 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jul
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Jul
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 140 reviews, 1 single bed, 1 bathroom
19–24 Sept
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 337 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
Guest favourite
Flat in Evanston
NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU
4.94 out of 5 average rating, 163 reviews, 3 bedrooms, 1 bathroom
24–29 Jul
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Guest favourite
Room in Chicago
Private Room in Norwood Park
4.98 out of 5 average rating, 43 reviews, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Guest favourite
Room in Niles
Private Furnished Bedroom in Chicago Surburb
4.82 out of 5 average rating, 89 reviews, 1 king bed, 1 bathroom
6–11 Jul
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept