
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
Superhost

Home in West Lawn
4.94 out of 5 average rating, 36 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Guest favourite

Flat in West Town
4.85 out of 5 average rating, 127 reviewsCondo with private terrace, free WIFI and parking
Superhost

Home in Schaumburg
4.8 out of 5 average rating, 81 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House
Top guest favourite

Flat in Albany Park
4.95 out of 5 average rating, 41 reviewsElegant 4Bedroom with Free Parking in Albany Park
Superhost

Flat in Jefferson Park
4.75 out of 5 average rating, 20 reviewsCity Gem: Stylish 3BR for Urban Explorers
Top guest favourite

Home in Lombard
5 out of 5 average rating, 23 reviewsSpacious Home in Chicago Suburbs
Superhost

Flat in Merrillville
4.83 out of 5 average rating, 87 reviewsLovely 2 Bed Room Apartment, all to yourself
Top guest favourite

Home in Chicago
5 out of 5 average rating, 19 reviewsComfy Home Away From Home
Quick stats about holiday rentals in Chicago
Total rentals
11K properties
Total number of reviews
534K 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
7K 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
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Rentals with an accessible-height bed Chicago
- Family-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with lake access Chicago
- Loft rentals Chicago
- Rentals with a balcony Chicago
- House rentals Chicago
- Rentals with beach access Chicago
- Bed and breakfasts Chicago
- Rentals with a washing machine and dryer Chicago
- Mansion rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a patio Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Fitness-friendly rentals Chicago
- Waterfront rentals Chicago
- Rentals with pools Chicago
- Townhouse rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Lakehouse rentals Chicago
- Rentals with a fireplace Chicago
- Private suite rentals Chicago
- Rentals with a sauna Chicago
- Flat rentals Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Frank Lloyd Wright Home and Studio
- Shedd Aquarium
- The Field Museum
- 875 North Michigan Avenue
- Illinois Beach State Park
- Woodlands Course at Whittaker
- Guaranteed Rate Field
- Skydeck Chicago
- Olympia Fields Country Club
- Odyssey Fun World
- Raging Waves Waterpark
- Flossmoor Golf Club
- Bengtson's Pumpkin Farm and Fall Fest
- Splash Station
- Deep River Waterpark
- Washington Park Zoo
- The Beverly Country Club
- Four Lakes Alpine Snowsports
- Frederick C. Robie House
- Museum of Science and Industry
- Things to do Chicago
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