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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Wrigleyville
Can't Beat This 2min Walk to Wrigley!
2 bedrooms, 5 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.81 out of 5 average rating, 288 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
1 bathroom
14–19 Oct
Featured hotel
Room in Downtown Chicago
Deluxe king non smoking
1 king bed, 1 bathroom
6–11 Sept
4.91 out of 5 average rating, 11 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 32 reviews
Guest favourite
Flat in West Side
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
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
28 Nov – 3 Dec
4.96 out of 5 average rating, 83 reviews
Guest favourite
Flat in West Town
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds, 2 bathrooms
1–6 Nov
4.9 out of 5 average rating, 300 reviews
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
22–27 Oct
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Apartment in Wicker Park
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, 168 reviews
Top guest favourite
Flat in Lake View
An elegant Chicago Northside Getaway
3 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 377 reviews
Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews