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Search results; Over 1,000 homes in Chicago

Top guest favourite
Place to stay in Chicago
Historic campus U of C Prof. mansion, top location
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
,
5.0 out of 5 average rating, 100 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
7–12 Jul
4.98 out of 5 average rating, 81 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
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
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
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
Apartment in Chicago
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds, 3 bathrooms
5–10 Jul
New place to stay
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 7 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
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
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 129 reviews
Guest favourite
Apartment in Chicago
12 Min Downtown, Free Parking, Rooftop, Sleeps 11
2 bedrooms, 8 beds, 2 bathrooms
5–10 Jul
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Aug
4.97 out of 5 average rating, 64 reviews
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
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds, 3.5 bathrooms
6–11 Jul
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Guest house in Oak Park
Coachhouse in central OP 4 blk to L
1 bedroom, 2 beds, 1 bathroom
9–14 Sept
4.9 out of 5 average rating, 555 reviews