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Search results; Over 1,000 homes in Chicago

Apartment in Chicago
Cabin 102 at 747 Lofts
Studio, 1 bed, 1 private bathroom
9–14 Aug
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4.77 out of 5 average rating, 115 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
27 Sept – 2 Oct
4.91 out of 5 average rating, 58 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest suite in Chicago
2BR/1.5 Bath in Logan Square
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.95 out of 5 average rating, 59 reviews
Guest favourite
Flat in Chicago
Upscale High-Rise Apt · Rooftop Pool + Views
1 bedroom, 1 double bed
27 Sept – 2 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed
19–24 Sept
4.94 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds
9–14 Aug
4.77 out of 5 average rating, 568 reviews
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
9–14 Aug
4.93 out of 5 average rating, 233 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 186 reviews
Top guest favourite
Apartment in Chicago
Bright, new 2BR in the heart of East Lakeview
2 bedrooms, 3 beds
23–28 Aug
4.99 out of 5 average rating, 128 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
16–21 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
26–31 Jul
4.99 out of 5 average rating, 348 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 54 reviews