
Holiday houses 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
4.93 out of 5 average rating, 42 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Guest favourite

Apartment in West Town
4.85 out of 5 average rating, 131 reviewsCondo with private terrace, free WIFI and parking
Guest favourite

Home in Chicago
5 out of 5 average rating, 7 reviewsBirthday?Anniversary?Showers?3500 sq ft, sleeps 16
Guest favourite

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

Apartment in Jefferson Park
4.64 out of 5 average rating, 28 reviewsCity Gem: Stylish 3BR for Urban Explorers
Top Guest favourite

Home in Lombard
5 out of 5 average rating, 27 reviewsSpacious Home in Chicago Suburbs
Superhost

Apartment in Merrillville
4.83 out of 5 average rating, 89 reviewsLovely 2 Bed Room Apartment, all to yourself
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
- Holland Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Haven Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Rentals with an accessible height bed Chicago
- Rentals with a fireplace Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Townhouse rentals Chicago
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- Condo rentals Chicago
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- Luxury rentals Chicago
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- Rentals with a washing machine and dryer Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Villa rentals Chicago
- Bed and breakfasts Chicago
- Rentals with beach access Chicago
- Smoking-friendly rentals Chicago
- Rentals with pools Chicago
- Waterfront rentals Chicago
- Lakehouse rentals Chicago
- Rentals with lake access Chicago
- Mansion rentals Chicago
- House rentals Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Oak Street Beach
- Humboldt Park
- Guaranteed Rate Field
- Six Flags Great America
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Museum of Science and Industry
- Wicker Park
- Flossmoor Golf Club
- Garfield Park Conservatory
- Chicago History Museum
- Illinois Beach State Park
- Washington Park Zoo
- Brookfield Zoo
- Chicago Cultural Center
- Things to do Chicago
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