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Search results; Over 1,000 homes in Chicago

Top guest favourite
Loft in Chicago
Tea Studio in Wicker Park Spring Factory
2 bedrooms, 2 beds, 2 private bathrooms
23–28 Oct
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4.96 out of 5 average rating, 307 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 167 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 28 reviews
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 146 reviews
Flat in Chicago
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds, 3.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 137 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews