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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
The Chicago River House – GIANT wall projector!
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Sept
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4.96 out of 5 average rating, 207 reviews
Room in Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
18–23 Aug
4.9 out of 5 average rating, 130 reviews
Guest favourite
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
17–22 Aug
4.71 out of 5 average rating, 17 reviews
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
16–21 Aug
New place to stay
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
1–6 Jan
4.95 out of 5 average rating, 127 reviews
Room in Bridgeport
Bridgeport Chicago near everything affordable.-5
1 double bed
6–11 Sept
New place to stay
Top guest favourite
Flat in Bridgeport
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
17–22 Aug
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in West Town
Luxury Penthouse Collection PH2 - Fulton Market
1 bedroom, 2 beds
7–13 Sept
New place to stay
Superhost
Flat in Chicago Loop
The Horizon | 3BR PH, 63rd Fl, Top Sky Deck
3 bedrooms, 4 beds
18–23 Aug
New place to stay
Superhost
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 1 bed
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Irving Park
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct