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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
Spectacular 2BR Penthouse in the Loop | Roof Deck
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.81 out of 5 average rating, 351 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
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 129 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
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
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
15–20 Aug
New place to stay
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 Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 15 reviews
Flat in Chicago
Bright & Cozy 1 Bdrm • Free Parking
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.57 out of 5 average rating, 58 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 35 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
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 79 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
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 18 reviews