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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Wrigleyville
Can't Beat This 2min Walk to Wrigley!
2 bedrooms, 5 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.81 out of 5 average rating, 279 reviews
Top guest favourite
Flat in Bridgeport
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
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
3–8 Jul
4.95 out of 5 average rating, 41 reviews
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Chicago Loop
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
Flat in West Side
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
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 19 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Apartment in West Side
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
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in West Side
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 140 reviews
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
4 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 51 reviews
Guest favourite
Flat in South Side
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
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 17 reviews