
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
Get the amount of space that is right for you.
Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Superhost

Private room in Hyde Park
4.83 out of 5 average rating, 35 reviewsHydeParkB, UC, Chinatown, NavyPier, freeparking
Guest favourite

Private room in Norwood Park
4.84 out of 5 average rating, 69 reviewsA comfortable home in Windy City

Private room in Chicago
4.73 out of 5 average rating, 40 reviewsBees Knees - Room 3
Guest favourite

Private room in Woodlawn
5 out of 5 average rating, 18 reviewsPrivate bath Hyde Park UChicago x2
Guest favourite

Private room in East Rogers Park
4.96 out of 5 average rating, 26 reviewsLoft Style Private Apt 4 (1 Room- 420 Friendly)
Guest favourite

Private room in South Shore
4.84 out of 5 average rating, 49 reviewsYellow Room - South Shore Bungalow
Top guest favourite

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

Private room in East Side
4.83 out of 5 average rating, 6 reviewsConfortable and affordable
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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- Rentals with beach access Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- 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
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Flossmoor Golf Club
- Things to do Chicago
- Food and drink Chicago
- Tours Chicago
- Sightseeing Chicago
- Art and culture Chicago
- Nature and outdoors Chicago
- Things to do Cook County
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- Things to do Illinois
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- Nature and outdoors Illinois
- Food and drink Illinois
- Tours Illinois
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Nature and outdoors United States
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- Entertainment United States