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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
13–18 Sept
,
4.97 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.87 out of 5 average rating, 15 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jan
4.95 out of 5 average rating, 127 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH2 - Fulton Market
1 bedroom, 2 beds, 1 bathroom
7–13 Sept
New place to stay
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 70 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 25 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
14–19 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago
West Loop 2BR : Skyline Views + Prime Location
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 69 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 385 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
21–26 Nov
4.96 out of 5 average rating, 597 reviews