
Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Superhost

Private room in Chicago
4.86 out of 5 average rating, 44 reviews23rd Pl 2D
Guest favourite

Private room in West Rogers Park
4.95 out of 5 average rating, 193 reviewsWelcoming Evanston Home
Guest favourite

Private room in East Rogers Park
4.95 out of 5 average rating, 43 reviewsPrivate Room in Rogers Park
Superhost

Private room in Evanston
4.83 out of 5 average rating, 92 reviewsFull Room|Near NU, Lakefront & Downtown Evanston!
Top guest favourite

Private room in Glen Ellyn
5 out of 5 average rating, 11 reviewsCozy Bedroom in House - 10 min from Metra
Guest favourite

Private room in East Side
4.87 out of 5 average rating, 15 reviewsQuiet and relaxing kind bed
Superhost

Private room in Skokie
4.9 out of 5 average rating, 41 reviewsCozy Private Room
Guest favourite

Private room in North Park
4.97 out of 5 average rating, 39 reviewsLovely master bedroom with private bath
Quick stats about vacation rentals in Chicago
Total rentals
11K properties
Total number of reviews
542K reviews
Family-friendly rentals
5.2K properties are a good fit for families
Pet-friendly rentals
3.6K properties allow pets
Rentals with a pool
1.2K properties have a pool
Rentals with dedicated workspaces
6.9K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Vacation rentals
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- Fitness-friendly rentals Chicago
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- Bed and breakfasts Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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- Art and culture Chicago
- Nature and outdoors Chicago
- Tours Chicago
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