filters

Search results; Over 1,000 homes in Chicago

Photo 1 of 29
Guest favourite
Flat in The Loop
1BR South Loop Loft I SuperHost + Top Rated!
1 bedroom, 3 beds, 1 private bathroom
14–20 Dec
,
4.89 out of 5 average rating, 308 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 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 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 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 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 Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
2–7 Jan
4.94 out of 5 average rating, 263 reviews
Photo 1 of 18
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 76 reviews
Photo 1 of 29
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 112 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 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 29
Superhost
Flat in Downtown Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
1–6 Nov
New place to stay
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 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 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 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, 136 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 20
Superhost
Flat in West Side
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 10
Top guest favourite
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 2 beds
11–16 Nov
5.0 out of 5 average rating, 14 reviews