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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Chicago
BnB on Grace Street - Modern 2-Bedroom Guest Suite
2 bedrooms, 3 beds, 1 private bathroom
24–29 Oct
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4.93 out of 5 average rating, 238 reviews
Superhost
Flat in Chicago
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
3 bedrooms, 3 beds
16–21 Aug
New place to stay
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
9–14 Aug
4.91 out of 5 average rating, 117 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds
17–22 Aug
New place to stay
Flat in Chicago
Spacious, Charming, Top Floor, Steps to Wrigley
3 bedrooms, 4 beds
16–21 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
11–16 Nov
4.96 out of 5 average rating, 305 reviews
Place to stay in Chicago
Charming Room in Historic Ukrainian Village!
1 bedroom, 1 queen bed
6–11 Sept
New place to stay
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Flat in Chicago
An elegant Chicago Northside Getaway
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 375 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
23–28 Aug
New place to stay
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Chicago
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