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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
1 bedroom, 2 beds, 1 private bathroom
9–14 Nov
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4.97 out of 5 average rating, 341 reviews
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 384 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.86 out of 5 average rating, 14 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 474 reviews
Guest favourite
Apartment in Chicago
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
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 70 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 915 reviews
Top guest favourite
Flat in Chicago
Modern 1 BR Near the L, Beach - Bright and Sunny!
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Chicago
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
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds, 1 bathroom
23–28 Oct
4.98 out of 5 average rating, 415 reviews
Guest favourite
Guest house in Villa Park
Eclectic Coach House Apartment
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 163 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 193 reviews
Top guest favourite
Flat in Oak Park
Modern+Spacious W/King Bed, Walk to Town-Park Free
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 245 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 103 reviews