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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
NEW luxury Old Town 1-Bedroom condo
1 bedroom, 1 bed, 1 shared bathroom
19–24 Sept
,
4.94 out of 5 average rating, 145 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
16–21 Aug
4.9 out of 5 average rating, 127 reviews
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed
25–30 Oct
4.93 out of 5 average rating, 59 reviews
Top guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds
23–28 Oct
4.98 out of 5 average rating, 417 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
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 14 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds
7–12 Sept
New place to stay
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds
1–6 Nov
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 56 reviews
Superhost
Flat in Oak Park
Bright Boho Haven free parking
1 bedroom, 1 king bed
30 Aug – 4 Sept
4.83 out of 5 average rating, 115 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
11–16 Nov
4.96 out of 5 average rating, 309 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
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, 26 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
15–20 Aug
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 385 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
1–6 Nov
4.97 out of 5 average rating, 35 reviews