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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Edgewater
Where you want to BE! Stylish, Comfy, Luxe
3 bedrooms, 6 beds, 1 private bathroom
7–12 Jul
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5.0 out of 5 average rating, 64 reviews
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
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 17 beds, 3.5 bathrooms
3–8 Jul
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 80 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jul
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
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 1 bathroom
21–26 Jul
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in South Side
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
Flat in West Rogers Park
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Guest favourite
Flat in West Side
Cozy Urban View Retreat Near Downtown - Sleeps 7
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 1 bathroom
13–18 Jul
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
5–10 Jul
Superhost
Flat in South Loop
Paradise Lounge South loop 3br W/ Balcony
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
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
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul