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

Home in West Lawn
4.92 out of 5 average rating, 39 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Guest favourite

Flat in West Town
4.85 out of 5 average rating, 130 reviewsCondo with private terrace, free WIFI and parking
Guest favourite

Flat in Albany Park
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
Superhost

Flat in Jefferson Park
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
Superhost

Apartment in East Rogers Park
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
Superhost

Home in Wood Dale
5 out of 5 average rating, 4 reviewsHome in the Woods!
Superhost

Home in Gary
4.91 out of 5 average rating, 74 reviewsLaurna Dune
Top guest favourite

Home in Chicago
5 out of 5 average rating, 21 reviewsComfy Home Away From Home
Quick stats about holiday 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 Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- Holland Holiday rentals
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- South Haven Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Rentals with a fireplace Chicago
- Lakehouse rentals Chicago
- Loft rentals Chicago
- Rentals with lake access Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
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- Private suite rentals Chicago
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- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with a patio Chicago
- Rentals with pools Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Guest house rentals Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- Museum of Science and Industry
- 875 North Michigan Avenue
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- Wicker Park
- Flossmoor Golf Club
- Garfield Park Conservatory
- Skokie Country Club
- Brookfield Zoo
- Willis Tower
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Washington Park Zoo
- Things to do Chicago
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- Art and culture Chicago
- Entertainment Chicago
- Wellness Chicago
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- Sightseeing Chicago
- Things to do Cook County
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- Things to do Illinois
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