
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

Private room in Evanston
4.83 out of 5 average rating, 92 reviewsFull Room|Near NU, Lakefront & Downtown Evanston!
Top guest favourite

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

Private room in South Loop
5 out of 5 average rating, 123 reviewsUrban Oasis Pilsen - guest room in townhouse
Superhost

Private room in Skokie
4.9 out of 5 average rating, 41 reviewsCozy Private Room
Top guest favourite

Private room in Hyde Park
4.91 out of 5 average rating, 243 reviewsFresh and Sunny Bed & Bath by UofC
Guest favourite

Private room in Pilsen
4.87 out of 5 average rating, 195 reviewsBOHEMIAN LODGE #1 (clean & affordable travel)
Guest favourite

Private room in Oak Park
5 out of 5 average rating, 11 reviewsDT Oak Park LUXE Private BR C | Queen Bed Sleeps 2
Superhost

Private room in Heart of Italy
4.84 out of 5 average rating, 38 reviews23rd Pl 4U
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
- Fitness-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Loft rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with a sauna Chicago
- Rentals with a washing machine and dryer Chicago
- Townhouse rentals Chicago
- Ski-in/ski-out rentals Chicago
- Villa rentals Chicago
- Family-friendly rentals Chicago
- Private suite rentals Chicago
- Flat rentals Chicago
- Rentals with a balcony Chicago
- Bed and breakfasts Chicago
- Beachfront rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with pools Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a patio Chicago
- Rentals with lake access Chicago
- House rentals Chicago
- Waterfront rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with beach access Chicago
- Lakehouse rentals Chicago
- Rentals with an accessible-height bed Chicago
- Mansion rentals Chicago
- Yurt Rentals United States
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- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
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- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
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- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
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- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- 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
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
- Food and drink Chicago
- Art and culture Chicago
- Sightseeing Chicago
- Tours Chicago
- Nature and outdoors Chicago
- Things to do Cook County
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- Things to do Illinois
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- Things to do United States
- Food and drink United States
- Tours United States
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- Nature and outdoors United States