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Search results; Over 1,000 homes in Chicago

Superhost
Home in West Side
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 private bathroom
7–12 Sept
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4.93 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jun
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 116 reviews
Superhost
Flat in West Town
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms, 6 beds, 3.5 bathrooms
22–27 Jun
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
30 Jun – 5 Jul
5.0 out of 5 average rating, 14 reviews
Flat in West Side
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Top guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 139 reviews
Flat in Logan Square
Retro Logan Square Retreat • Blue Line
1 bedroom, 1 bunk bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
28 Jun – 3 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms, 3 queen beds, 1 bathroom
3–8 Jul
New place to stay
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds, 1 bathroom
28 Jun – 3 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 50 reviews
Home in Humboldt Park
Newly Renovated Home 4BD/3BTH with garage!
4 bedrooms, 5 beds, 3 bathrooms
4–9 Aug
New place to stay
Guest favourite
Flat in Wicker Park
4 Bedroom Penthouse Loft in Heart of Wicker Park
4 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms, 3 beds, 1 bathroom
26–31 Jul