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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Lincoln Park
Spacious Luxury Townhouse - Old Town
3 bedrooms, 3 beds, 2.5 private bathrooms
21–26 Aug
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4.83 out of 5 average rating, 282 reviews
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
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
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
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
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
16–21 Aug
Guest favourite
Apartment in Bronzeville
Ultimate Group Experience Entire Building Chicago
4.8 out of 5 average rating, 10 reviews, 9 bedrooms, 15 beds, 6 bathrooms
29 Aug – 3 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 Ukrainian Village
Stylish & Spacious Multi-Level Apt in Wicker Park
4.96 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Flat in West Rogers Park
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Downtown Chicago
Modern 3BR Apartment Near North Ave Shops
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
4.88 out of 5 average rating, 433 reviews, 2 bedrooms, 3 beds, 1 bathroom
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, 18 beds, 3.5 bathrooms
2–7 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
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 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
16–21 Aug
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug