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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in West Loop
Modern long-term luxury w/ spectacular view!
1 bedroom, 1 bed, 2 private bathrooms
23–28 Sept
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4.96 out of 5 average rating, 50 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
21–26 Oct
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
9–14 Jan
4.96 out of 5 average rating, 83 reviews
Featured hotel
Rooms in Downtown Chicago
Junior two bedroom suite
2 bedrooms
27 Sept – 2 Oct
Top guest favourite
Flat in Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds
26–31 Oct
4.96 out of 5 average rating, 143 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 Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 35 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, 62 reviews
Featured hotel
Room in Downtown Chicago
Deluxe king non smoking
1 king bed
6–11 Sept
4.91 out of 5 average rating, 11 reviews
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
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 961 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
Guest favourite
Room in Downtown Chicago
Deluxe King Room · Juliette Balcony · Sono B&B
1 king bed
3–8 Oct
5.0 out of 5 average rating, 17 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 Wicker Park
【Central】- Eclectic Fun 1BR APT in Wicker Park
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.95 out of 5 average rating, 165 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, 66 reviews
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds
28 Nov – 3 Dec
4.98 out of 5 average rating, 91 reviews
Top 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
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