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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Downtown Chicago
Modern 3BR with Private Rooftop & Free Parking
3 bedrooms, 7 beds, 2.5 private bathrooms
17–22 Sept
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4.92 out of 5 average rating, 186 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds
25–30 Oct
4.98 out of 5 average rating, 253 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
6–11 Sept
New place to stay
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Flat in Ravenswood
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 65 reviews
Guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Room in Lincoln Park
Quaint Cozy Vintage for two in Lincoln Park
1 queen bed
28 Oct – 2 Nov
4.9 out of 5 average rating, 67 reviews
Top guest favourite
Flat in Downtown Chicago
Highrise Hideout (Fitness Center • Sauna)
2 bedrooms, 3 beds
6–11 Sept
4.92 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 27 reviews
Superhost
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 70 reviews
Top guest favourite
Apartment in Ravenswood
Lincoln Square Gem!
2 bedrooms, 2 queen beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 505 reviews
Flat in West Side
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds
6–11 Sept
New place to stay