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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Wrigleyville Inn. Historic Greystone, Free Parking
3 bedrooms, 3 beds, 2 private bathrooms
4–9 Oct
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4.99 out of 5 average rating, 118 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds, 6 bathrooms
29 Aug – 3 Sept
4.8 out of 5 average rating, 10 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds, 2 bathrooms
22–27 Aug
New place to stay
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
New place to stay
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 141 reviews
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
4.94 out of 5 average rating, 66 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 183 reviews
Guest favourite
Apartment in Chicago
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
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 74 reviews
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
4.97 out of 5 average rating, 161 reviews
Guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds, 3.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 22 reviews