
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
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Guest favourite

Private room in West Rogers Park
4.94 out of 5 average rating, 196 reviewsWelcoming Evanston Home
Superhost

Private room in River North
4.88 out of 5 average rating, 217 reviewsChicago Speakeasy-Style Loft (Room 2B)
Top guest favourite

Private room in Elmhurst
4.99 out of 5 average rating, 217 reviewsChic Oasis near Downtown Chicago
Guest favourite

Private room in Evanston
4.91 out of 5 average rating, 107 reviewsRoom Mins to Downtown Chicago & Northwestern!
Top guest favourite

Private room in Glen Ellyn
5 out of 5 average rating, 11 reviewsCozy Bedroom in House - 10 min from Metra
Superhost

Private room in Chicago
4.82 out of 5 average rating, 508 reviewsFlorence Room - 3min to CTA, Free Parking, Roomy
Guest favourite

Private room in Norwood Park
4.77 out of 5 average rating, 320 reviewsChicago River Room near USMLE
Guest favourite

Hotel room in The Loop
5 out of 5 average rating, 8 reviewsNewly reno’d king room with sweet city views
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
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with an accessible-height bed Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a sauna Chicago
- Townhouse rentals Chicago
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- Rentals with a washing machine and dryer Chicago
- Rentals with lake access Chicago
- Ski-in/ski-out rentals Chicago
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- Rentals with an EV charger Chicago
- Rentals with a patio Chicago
- Private suite rentals Chicago
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- Villa rentals Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Wicker Park
- Washington Park Zoo
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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- Things to do United States
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