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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Uptown
Cozy loft in Chicago's Uptown
1 bedroom, 2 beds, 1 private bathroom
4–9 Jul
,
4.97 out of 5 average rating, 331 reviews
Home in Humboldt Park
Newly Renovated Home 4BD/3BTH with garage!
4 bedrooms5 beds, 3 bathrooms,
28 Jun – 3 Jul
New place to stay
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms8 beds, 3 bathrooms,
23–28 Aug
4.91 out of 5 average rating, 117 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms3 beds, 1.5 bathrooms,
12–17 Oct
4.95 out of 5 average rating, 113 reviews
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms3 beds, 1 bathroom,
26–31 Jul
Flat in Logan Square
Retro Logan Square Retreat • Blue Line
1 bedroom1 bunk bed, 1 bathroom,
4–9 Jul
New place to stay
Guest favourite
Room in Norwood Park
Private Room in Norwood Park
1 bed1 bathroom,
14–19 Jun
4.97 out of 5 average rating, 36 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms2 bathrooms,
30 Aug – 4 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms3 beds, 2 bathrooms,
7–12 Jun
4.94 out of 5 average rating, 65 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom1 queen bed, 1 bathroom,
30 Aug – 4 Sept
4.97 out of 5 average rating, 894 reviews
Superhost
Flat in West Side
Luxe 4BR Brick & Stone by Douglass Park + Med Dist
4 bedrooms4 beds, 2 bathrooms,
7–12 Jun
Guest favourite
Apartment in North Side
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
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms3 beds, 1 bathroom,
14–19 Jun
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms3 beds, 2.5 bathrooms,
17–22 Aug
4.98 out of 5 average rating, 56 reviews
Flat in West Rogers Park
West Ridge 2BR Retreat with Laundry | Near Loyola
2 bedrooms2 beds, 2 bathrooms,
21–26 Jun
New place to stay
Home in South Side
Steps to Lake & Beach! Multi-Level Oakland Haven
4 bedrooms5 beds, 4.5 bathrooms,
29 Jun – 4 Jul
New place to stay
Home in North Side
5BR Logan Sq | Sleeps 10 | Outdoor, Parking, Games
5 bedrooms5 queen beds, 2 bathrooms,
7–12 Jun
New place to stay
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms4 beds, 2 bathrooms,
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms2 queen beds, 1 bathroom,
15–20 Nov
4.99 out of 5 average rating, 937 reviews