filters

Search results; Over 1,000 homes in Chicago

Photo 1 of 26
Top guest favourite
Guest suite in Ravenswood
Private Lincoln Square one bed+bath studio apt.
1 bedroom, 1 bed, 1 private bathroom
16–21 Nov
,
4.99 out of 5 average rating, 442 reviews
Photo 1 of 29
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
8–13 Nov
5.0 out of 5 average rating, 36 reviews
Photo 1 of 29
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
8–13 Nov
4.9 out of 5 average rating, 126 reviews
Photo 1 of 28
Guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
18–23 Jan
4.95 out of 5 average rating, 318 reviews
Photo 1 of 12
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 135 reviews
Photo 1 of 6
Guest favourite
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed
5–10 Nov
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
1–6 Nov
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 263 reviews
Photo 1 of 26
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 965 reviews
Photo 1 of 15
Flat in West Side
Luxury penthouse with city views
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 23
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 62 reviews
Photo 1 of 9
Top guest favourite
Guest suite in North Side
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed
15–20 Nov
4.92 out of 5 average rating, 545 reviews
Photo 1 of 11
Top guest favourite
Guest suite in Andersonville
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed
15–20 Nov
4.96 out of 5 average rating, 417 reviews
Photo 1 of 13
Top guest favourite
Flat in Lake View
Chic retreat near the best of Lakeview & Wrigley
1 bedroom, 1 queen bed
1–6 Nov
4.93 out of 5 average rating, 196 reviews
Photo 1 of 20
Top guest favourite
Guest suite in Portage Park
Eddy Street Upstairs Apartment
1 bedroom, 1 bed
2–7 Nov
4.94 out of 5 average rating, 178 reviews
Photo 1 of 22
Top guest favourite
Flat in South Side
European Coziness in Bronzeville
3 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
Photo 1 of 21
Top guest favourite
Flat in Edgewater
Andersonville Living
3 bedrooms, 5 beds
2–7 Nov
4.94 out of 5 average rating, 501 reviews
Photo 1 of 29
Top guest favourite
Flat in Logan Square
Your Logan Square Oasis with Lush Outdoor Haven!
2 bedrooms, 2 king beds
1–6 Nov
5.0 out of 5 average rating, 39 reviews
Photo 1 of 29
Top guest favourite
Guest suite in Ravenswood
Private suite in Lincoln Square
1 bedroom, 1 queen bed
18–23 Oct
4.97 out of 5 average rating, 486 reviews