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Search results; Over 1,000 homes in Chicago

Top guest favourite
Loft in Wicker Park
Modern LOFT Ukrainian Village 2nd floor
Studio, 1 bed, 1 private bathroom
30 Aug – 4 Sept
,
4.95 out of 5 average rating, 162 reviews
Guest favourite
Flat in Chicago Loop
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 Downtown 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 Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jan
4.95 out of 5 average rating, 127 reviews
Top guest favourite
Flat in Bridgeport
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
Flat in Bridgeport
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
Superhost
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 1 bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Room in Belmont Cragin
Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan
1 queen bed, 1.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 55 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 309 reviews
Top guest favourite
Flat in Irving Park
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
Top guest favourite
Flat in West Side
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
Room in South Side
Room w/ Private Bath | Chicago IL
1 queen bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Flat in West Town
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
Flat in West Rogers Park
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