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Search results; Over 1,000 homes in Chicago

Apartment in Lincoln Park
Modern Luxury In Old Town - Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Aug
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4.76 out of 5 average rating, 274 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, 126 reviews
Guest favourite
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.87 out of 5 average rating, 15 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 165 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 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
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
6–11 Sept
New place to stay
Guest favourite
Room in Norwood Park
Private Bedroom By O’hare (Norwood Park)
1 bed, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 11 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
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Flat in Logan Square
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 17 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
Guest favourite
Flat in Downtown Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 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 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, 17 reviews
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 4 reviews