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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Spacious 2 Bedroom in the heart of Lakeview!
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
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4.99 out of 5 average rating, 159 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
7–12 Aug
New place to stay
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds
17–22 Oct
4.98 out of 5 average rating, 412 reviews
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
19–24 Sept
5.0 out of 5 average rating, 6 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
Superhost
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, 164 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
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
24–29 Oct
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds
20–25 Sept
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
16–21 Aug
4.93 out of 5 average rating, 344 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed
4–9 Oct
4.95 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Forest Park
Cheerful Remodel Prime Location
1 bedroom, 1 queen bed
1–6 Nov
4.92 out of 5 average rating, 148 reviews
Guest favourite
Flat in Oak Park
Bright Boho Haven free parking
1 bedroom, 1 king bed
11–16 Sept
4.83 out of 5 average rating, 112 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Townhouse in Oak Park
A Pleasant Stay in Oak Park
2 bedrooms, 2 beds
9–14 Nov
4.99 out of 5 average rating, 75 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 11 reviews