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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.92 out of 5 average rating, 74 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Room in Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds
6–11 Sept
New place to stay
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
6–11 Sept
New place to stay
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 522 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
7–12 Sept
4.88 out of 5 average rating, 146 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, 32 reviews
Flat in Chicago
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds
6–11 Sept
New place to stay
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds
25–30 Oct
4.96 out of 5 average rating, 137 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews