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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
,
4.97 out of 5 average rating, 37 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
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 906 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
16–21 Jul
4.97 out of 5 average rating, 89 reviews
Place to stay in Chicago
Self check in 24h near downtown Chicago p2
1 bedroom, 1 queen bed, 2 bathrooms
8–13 Aug
New place to stay
Superhost
Flat in Chicago
Renovated 2BR in Prime L. | Sleeps 6 |Pet Friendly
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
New place to stay
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Chicago
Elegant Modern-Luxury Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 247 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 349 reviews
Guest favourite
Flat in Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
2 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
4.93 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 260 reviews
Top 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, 119 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
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
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 65 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 13 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
Top guest favourite
Flat in Chicago
The Logan Greystone
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.98 out of 5 average rating, 66 reviews