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Search results; Over 1,000 homes in Chicago

Top guest favourite
Bungalow in Chicago
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 158 reviews
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 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 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 Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Guest favourite
Apartment in Chicago
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
Top guest favourite
Room in Chicago
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
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 13 reviews
Townhouse in Chicago
Walk to United Center 9 mins-Downtown FreeParking
3 bedrooms, 3 beds, 3 bathrooms
5–10 Jul
4.71 out of 5 average rating, 7 reviews
Guest favourite
Flat in Chicago
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
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 81 reviews
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds, 1 bathroom
26 Jun – 1 Jul
New place to stay
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 123 reviews
Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Jun – 3 Jul
4.99 out of 5 average rating, 299 reviews
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jun
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 116 reviews