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Search results; Over 1,000 homes in Chicago

Superhost
Apartment in West Side
Spacious 5-BR Apt next to transit Free Parking
5 bedrooms, 5 beds, 1.5 shared bathrooms
18–23 Oct
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4.89 out of 5 average rating, 114 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 85 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in South Side
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
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 233 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 18 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4.98 out of 5 average rating, 40 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Jul
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
4.95 out of 5 average rating, 107 reviews, 3 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Superhost
Flat in Downtown Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
New place to stay, 3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Flat in Rogers Park Township
2BR/1BA Apt w/ Modern Amenities Rogers Park
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug