
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, 110 reviewsLovely Garden Studio in Chicago
Guest favourite

Flat in Chicago
5 out of 5 average rating, 7 reviewsSunny Penthouse - Oakwood Beach
Superhost

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

Flat in West Loop
4.94 out of 5 average rating, 80 reviewsFulton House #1 (2bd/ 1ba)
Top guest favourite

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

Hotel room in Rosemont
4.9 out of 5 average rating, 312 reviewsRelaxing Standard Room l Free Airport Shuttle
Superhost

Private room in Chicago
4.81 out of 5 average rating, 58 reviewsCottage Crafts Room - Free Parking, 1 block to CTA
Guest favourite

Flat in River North
4.87 out of 5 average rating, 52 reviewsRiver North | Private Balcony With In&Out Parking
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 ChicagoĀ Holiday rentals
- MilwaukeeĀ Holiday rentals
- Lake GenevaĀ Holiday rentals
- West SideĀ Holiday rentals
- North SideĀ Holiday rentals
- South BendĀ Holiday rentals
- South HavenĀ Holiday rentals
- HollandĀ Holiday rentals
- SaugatuckĀ Holiday rentals
- South SideĀ Holiday rentals
- Lake Michigan BeachĀ Holiday rentals
- EvanstonĀ Holiday rentals
- Fitness-friendly rentalsĀ Chicago
- Rentals with a cinemaĀ Chicago
- Rentals with outdoor seatingĀ Chicago
- Hotel rentalsĀ Chicago
- Pet-friendly rentalsĀ Chicago
- Flat rentalsĀ Chicago
- Mansion rentalsĀ Chicago
- Rentals with an EV chargerĀ Chicago
- Private suite rentalsĀ Chicago
- Rentals with a saunaĀ Chicago
- Townhouse rentalsĀ Chicago
- Rentals with beach accessĀ Chicago
- Loft rentalsĀ Chicago
- Beachfront rentalsĀ Chicago
- Ski-in/ski-out rentalsĀ Chicago
- Waterfront rentalsĀ Chicago
- Rentals with poolsĀ Chicago
- Villa rentalsĀ Chicago
- House rentalsĀ Chicago
- Lakehouse rentalsĀ Chicago
- Rentals with a patioĀ Chicago
- Rentals with breakfastĀ Chicago
- Rentals with a firepitĀ Chicago
- Family-friendly rentalsĀ Chicago
- Apartment rentalsĀ Chicago
- Rentals with a hot tubĀ Chicago
- Rentals with an accessible-height bedĀ Chicago
- Smoking-friendly rentalsĀ Chicago
- Rentals with a fireplaceĀ Chicago
- Rentals with a washing machine and dryerĀ Chicago
- Rentals with lake accessĀ Chicago
- Bed and breakfastsĀ Chicago
- Rentals with a balconyĀ Chicago
- Yurt RentalsĀ United States
- Yurt RentalsĀ United Kingdom
- Castle RentalsĀ United States
- HouseboatsĀ United States
- Holiday CaravansĀ United Kingdom
- Private Island RentalsĀ United States
- Farm HousesĀ United States
- Farm CottagesĀ United Kingdom
- Cabin RentalsĀ Australia
- Luxury CabinsĀ United Kingdom
- Luxury CabinsĀ United States
- Holiday ChaletsĀ United Kingdom
- Cottage RentalsĀ United States
- Holiday CottagesĀ United Kingdom
- Mansion RentalsĀ United States
- Villa RentalsĀ United Kingdom
- Holiday BungalowsĀ United Kingdom
- Bungalow RentalsĀ United States
- Condo RentalsĀ United States
- Holiday ApartmentsĀ Australia
- Holiday HousesĀ United States
- Holiday HousesĀ United Kingdom
- Private Holiday RentalsĀ United Kingdom
- Big House RentalsĀ United States
- Big CottagesĀ Australia
- Large VillasĀ United Kingdom
- House Rentals with a PoolĀ United States
- Cabin Rentals with a PoolĀ United States
- Villas with a PoolĀ United Kingdom
- Apartments with a Hot TubĀ United States
- Holiday Cottages with a Hot TubĀ United Kingdom
- Beach CabinsĀ United States
- Beach CondosĀ United States
- Beachfront RentalsĀ United States
- Beach HousesĀ United Kingdom
- Beach VillasĀ United Kingdom
- Coastal CottagesĀ United Kingdom
- Pet-Friendly Vacation RentalsĀ United States
- Pet-Friendly Beach RentalsĀ United States
- Pet-Friendly Cabin RentalsĀ United States
- Dog-Friendly CottagesĀ United Kingdom
- Luxury Dog-Friendly CottagesĀ 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 doĀ Chicago
- Food and drinkĀ Chicago
- SightseeingĀ Chicago
- Art and cultureĀ Chicago
- Nature and outdoorsĀ Chicago
- ToursĀ Chicago
- Things to doĀ Cook County
- Food and drinkĀ Cook County
- Art and cultureĀ Cook County
- ToursĀ Cook County
- SightseeingĀ Cook County
- Things to doĀ Illinois
- Nature and outdoorsĀ Illinois
- ToursĀ Illinois
- Art and cultureĀ Illinois
- SightseeingĀ Illinois
- Food and drinkĀ Illinois
- Things to doĀ United States
- SightseeingĀ United States
- EntertainmentĀ United States
- Sports activitiesĀ United States
- Art and cultureĀ United States
- ToursĀ United States
- Nature and outdoorsĀ United States
- WellnessĀ United States
- Food and drinkĀ United States