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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in West Side
The Upscale Getaway Near Downtown
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Aug
,
4.93 out of 5 average rating, 294 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
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
5–10 Jul
4.95 out of 5 average rating, 41 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
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in South Side
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
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 113 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
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
Top guest favourite
Flat in West Town
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Ukrainian Village
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 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
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, 12 reviews
Guest favourite
Home in Wrigleyville
*New* Luxury Wrigley Penthouse, Free Parking
3 bedrooms, 6 beds, 2.5 bathrooms
5–10 Jul
4.92 out of 5 average rating, 50 reviews
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
4.97 out of 5 average rating, 155 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Flat in West Side
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews