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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
1,800ft² Parking Workspace W/D Full Kitch
2 bedrooms, 4 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.99 out of 5 average rating, 215 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
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
2–7 Nov
4.95 out of 5 average rating, 165 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
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
Flat in Chicago
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
Superhost
Flat in Oak Park
Bright Boho Haven free parking
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.82 out of 5 average rating, 114 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
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
Flat in Oak Park
A Quiet Stay While You Are Away Oak Park
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 205 reviews
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
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 94 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
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
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 164 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 51 reviews