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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
,
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Place to stay in Berwyn
room in family home
1 bedroom1 bed, 1 bathroom,
1–6 Dec
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed1 bathroom,
14–19 Mar
4.96 out of 5 average rating, 308 reviews
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms2 beds, 1 bathroom,
16–21 Aug
4.99 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms3 beds, 1 bathroom,
5–10 Jul
4.99 out of 5 average rating, 342 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms4 beds, 1 bathroom,
21–26 Sept
4.9 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms5 beds, 1 bathroom,
23–28 Aug
4.92 out of 5 average rating, 245 reviews
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms2 beds, 1 bathroom,
5–10 Aug
4.92 out of 5 average rating, 49 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms2 beds, 2 bathrooms,
5–10 Jul
4.95 out of 5 average rating, 155 reviews
Guest favourite
Flat in Chicago
4 Bedroom Penthouse Loft in Heart of Wicker Park
4 bedrooms6 beds, 2 bathrooms,
21–26 Jun
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom1 bed, 1 bathroom,
24–29 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Apartment in Chicago
Brand New Luxury space + roof deck!
3 bedrooms5 beds, 2 bathrooms,
14–19 Jun
4.93 out of 5 average rating, 61 reviews
Top guest favourite
Place to stay in Chicago
Private, dog-friendly room near downtown Chicago
1 bedroom1 sofa bed, 1 bathroom,
29 Jun – 4 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Chicago
The Cozy Suite
2 bedrooms4 beds, 1 bathroom,
5–10 Jul
4.86 out of 5 average rating, 42 reviews
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms3 beds, 2 bathrooms,
21–26 Jun
4.94 out of 5 average rating, 66 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms2 bathrooms,
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
The Logan Greystone
3 bedrooms3 beds, 1 bathroom,
30 Aug – 4 Sept
4.98 out of 5 average rating, 61 reviews
Guest favourite
Flat in Chicago
Comfy 2BR-2BTH | Steps to The Bean & Michigan Ave
2 bedrooms3 beds, 2 bathrooms,
19–24 Jul
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Chicago
Stylish Gold Coast 3BR Apt | Walk to Grocery&Cafes
3 bedrooms4 beds, 2 bathrooms,
6–11 Jul
4.98 out of 5 average rating, 47 reviews