
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

Loft in Chicago
4.99 out of 5 average rating, 111 reviewsLovely Garden Studio in Chicago
Guest favourite

Flat in Chicago
5 out of 5 average rating, 10 reviewsSunny Penthouse - Oakwood Beach
Top guest favourite

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

Flat in The Loop
4.8 out of 5 average rating, 303 reviewsKasa | Studio, Walk to Grant Park | South Loop
Guest favourite

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

Flat in River North
4.95 out of 5 average rating, 92 reviewsMag Mile Retreat: Stunning Views, High-End 2BR

Flat in Avondale
5 out of 5 average rating, 4 reviewsModern Design 3 Bedroom Dandelion Apartment
Superhost

Hotel room in The Loop
4.8 out of 5 average rating, 249 reviewsAll-glass gem by Chicago architect Harry Weese
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
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Villa rentals Chicago
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- Bed and breakfasts 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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