
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

Private room in Englewood
New place to stayComfortable Private 1 bedroom

Hotel room in River North
4.55 out of 5 average rating, 144 reviewsOnsite spa and indoor/outdoor rooftop bar

Private room in Douglas Park
4.57 out of 5 average rating, 258 reviewsFrida 2720 (2F)

Hotel room in Magnificent Mile
4.8 out of 5 average rating, 30 reviewsAdventure Awaits! Close to 360 Chicago! Parking!

Shared hotel room in Near North Side
New place to stayConvenient Stay In The Heart of River North

Private room in Chicago
4.69 out of 5 average rating, 26 reviewsR4 Close to Downtown Small Room

Hotel room in River North
4.59 out of 5 average rating, 657 reviewsPlayful spirit and sustainable practices
Guest favourite

Private room in North Park
4.89 out of 5 average rating, 71 reviewsPrivate Bedroom in Chicago (North Park)
Quick stats about holiday rentals in Chicago
Total rentals
11K properties
Total number of reviews
544K reviews
Family-friendly rentals
5.3K 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
6.8K properties have a dedicated workspace
Destinations to explore
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
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- St. Louis Holiday rentals
- Detroit Holiday rentals
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- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Bed and breakfasts Chicago
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- Rentals with a patio Chicago
- Waterfront rentals Chicago
- Mansion rentals Chicago
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- Flat rentals Chicago
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- Villa rentals Chicago
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Illinois Beach State Park
- Lincoln Park Zoo
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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- Art and culture Chicago
- Tours Chicago
- Nature and outdoors Chicago
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- Things to do Illinois
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