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Search results; Over 1,000 homes in Chicago

Superhost
Hotel room in Wicker Park
Romantic King Room in Boutique Wicker Park B&B
1 bedroom, 1 bed, 2 private bathrooms
23–28 Oct
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4.82 out of 5 average rating, 28 reviews
Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
Room in Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
7–12 Sept
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, 130 reviews
Room in Bridgeport
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
22–27 Aug
New place to stay
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
20–25 Aug
4.89 out of 5 average rating, 136 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, 29 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
Superhost
Flat in Uptown
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Home in West Town
6BR Humboldt Park Home | Speakeasy + Hot Tub
7 bedrooms, 12 beds
29 Aug – 3 Sept
New place to stay
Top guest favourite
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 1 bed
19–24 Oct
5.0 out of 5 average rating, 5 reviews
Flat in Lake View
Greek Consulate Historical Blg | Lincoln Park - 1
6 bedrooms, 7 beds
18–23 Aug
New place to stay
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 22 reviews
Superhost
Flat in Chicago Loop
The Horizon | 3BR PH, 63rd Fl, Top Sky Deck
3 bedrooms, 4 beds
20–25 Aug
New place to stay
Flat in Logan Square
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds
18–23 Aug
New place to stay
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 reviews
Home in Edgewater
House in Chicago
4 bedrooms, 5 beds
19–24 Aug
5.0 out of 5 average rating, 4 reviews