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Search results; Over 1,000 homes in Chicago

Guest favourite
Loft in Chicago
OHC Gorgeous Huge Studio Apt Steps to Blue Line
Studio, 3 beds, 1 private bathroom
29 Aug – 3 Sept
,
4.9 out of 5 average rating, 403 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, 128 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds
7–12 Sept
New place to stay
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
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
Superhost
Guest house in Chicago
Horner Park Coach House
1 bedroom, 1 bed
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 3 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
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
14–19 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 20 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
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
14–19 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 18 reviews
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
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
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 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