
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
Guest favourite

Private room in Chicago
4.85 out of 5 average rating, 54 reviewsA3-Next to the Train & Downtown
Guest favourite

Private room in Belmont Cragin
4.92 out of 5 average rating, 24 reviewsPrivate RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan

Private room in Englewood
New place to stayComfortable Private 1 bedroom
Guest favourite

Private room in Woodlawn
5 out of 5 average rating, 30 reviewsPrivate bath Hyde Park UChicago x2
Guest favourite

Private room in North Park
4.86 out of 5 average rating, 35 reviewsSimple, Private Bedroom (North Park)
Guest favourite

Private room in North Park
4.98 out of 5 average rating, 49 reviewsLovely master bedroom with private bath
Superhost

Private room in Chicago
4.85 out of 5 average rating, 41 reviews23rd Pl 4U
Guest favourite

Private room in Melrose Park
4.96 out of 5 average rating, 94 reviews4 miles to Airport, King bed, 45 in TV
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
- Ski-in/ski-out rentals Chicago
- Rentals with an accessible-height bed Chicago
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- Rentals with pools Chicago
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- Villa rentals Chicago
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- Serviced apartment rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with lake access Chicago
- House rentals Chicago
- Townhouse rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating 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
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
- Food and drink Chicago
- Sightseeing Chicago
- Sports activities Chicago
- Art and culture Chicago
- Nature and outdoors Chicago
- Tours Chicago
- Things to do Cook County
- Food and drink Cook County
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- Things to do Illinois
- Art and culture Illinois
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- Sightseeing Illinois
- Things to do United States
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