filters

Search results; Over 1,000 homes in Chicago

Photo 1 of 29
Top guest favourite
Home in Chicago
Cozy garden apartment historic Jackson Bvld.
1 bedroom, 1 bed, 1 shared bathroom
19–24 Oct
,
4.98 out of 5 average rating, 384 reviews
Photo 1 of 15
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
8–13 Nov
4.9 out of 5 average rating, 126 reviews
Photo 1 of 28
Guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jan
4.95 out of 5 average rating, 318 reviews
Photo 1 of 29
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 36 reviews
Photo 1 of 29
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 112 reviews
Photo 1 of 12
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 135 reviews
Photo 1 of 6
Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 7 reviews
Photo 1 of 9
Top guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.92 out of 5 average rating, 545 reviews
Photo 1 of 29
Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 263 reviews
Photo 1 of 22
Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
Photo 1 of 6
Top guest favourite
Room in Oak Park
Antique Filled Home
1 bed, 1 bathroom
1–6 Dec
4.94 out of 5 average rating, 448 reviews
Photo 1 of 29
Top guest favourite
Flat in Chicago
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds, 1 bathroom
3–8 Jan
4.98 out of 5 average rating, 260 reviews
Photo 1 of 20
Superhost
Flat in Chicago
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 18
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.95 out of 5 average rating, 76 reviews
Photo 1 of 20
Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 178 reviews
Photo 1 of 6
Guest favourite
Room in Chicago
Quaint Cozy Vintage for two in Lincoln Park
1 queen bed, 1 bathroom
9–14 Nov
4.9 out of 5 average rating, 69 reviews
Photo 1 of 21
Top guest favourite
Apartment in Chicago
Two Bedroom w Porch in Wicker Park
2 bedrooms, 2 beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 123 reviews