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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Chicago
New Bright & Airy Entire Unit in Logan
1 bedroom, 1 bed, 1 private bathroom
29 Aug – 3 Sept
,
4.91 out of 5 average rating, 197 reviews
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
12–17 Aug
4.9 out of 5 average rating, 124 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 165 reviews
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 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, 415 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
Superhost
Flat in Oak Park
Bright Boho Haven free parking
1 bedroom, 1 king bed
6–11 Sept
4.82 out of 5 average rating, 114 reviews
Top guest favourite
Room in Chicago
West Beverly’s Gem-Private bedroom #1
1 queen bed
24–29 Aug
4.95 out of 5 average rating, 99 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 55 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, 103 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
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
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds
1–6 Nov
4.94 out of 5 average rating, 474 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
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
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
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, 34 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
Top guest favourite
Home in Lombard
Modern Boho house in Lombard 7 min to Metra
2 bedrooms, 3 beds
16–21 Aug
4.99 out of 5 average rating, 151 reviews