
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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Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Top guest favourite

Home in Schaumburg
5 out of 5 average rating, 50 reviewsGreat location-King beds-Kids playroom
AdamRating, 5 stars2 weeks ago
Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.
Top guest favourite

Home in Avondale
5 out of 5 average rating, 11 reviewsAlluring Avondale Abode
MichaelRating, 5 stars1 week ago
Bethâs home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.
Superhost

Guest suite in Lincoln Park
4.75 out of 5 average rating, 8 reviewsThe Hidden Beach House
GaryRating, 5 stars1 month ago
I enjoyed my stay here. The accommodations were basic, but the place was very clean and quiet, I found the bed very comfortable, and the location was ideal for 1 to 2 people to base out of while enjoying Old Town. The Brown Line train is just a couple of blocks from the house, which made getting to the Loop very convenient. Caid was very easy to reach with any questions. I would stay here again. One recommendation: if you drive here and need a parking pass, make those arrangements well in advance of your arrival, because they canât be provided at a momentâs notice. I waited until the day before to ask for one and could not get it, so I had to pay $90 to park in a garage.
Guest favourite

Home in Chicago
5 out of 5 average rating, 5 reviewsBirthday?Anniversary?Showers?3500 sq ft, sleeps 16
ArissRating, 5 stars1 week ago
Vinceâs place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future
Guest favourite

Flat in Albany Park
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Flat in Jefferson Park
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars3 weeks ago
Peaceful, felt like home, very spacious and comfortable
Top guest favourite

Home in Lombard
5 out of 5 average rating, 25 reviewsSpacious Home in Chicago Suburbs
JenniferRating, 5 stars1 week ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Superhost

Home in Austin
4.85 out of 5 average rating, 68 reviewsA Comfortable Stay While You are Away in Oak Park
KarenRating, 5 stars1 week ago
The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.
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
- Lake Michigan Beach Holiday rentals
- Holland Holiday rentals
- South Side Holiday rentals
- South Haven Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Private suite rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a sauna Chicago
- Rentals with an accessible-height bed Chicago
- Bed and breakfasts Chicago
- Villa rentals Chicago
- Loft rentals Chicago
- House rentals Chicago
- Mansion rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Guest house rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Townhouse rentals Chicago
- Rentals with a patio Chicago
- Smoking-friendly rentals Chicago
- Flat rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with beach access Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with lake access Chicago
- Lakehouse rentals Chicago
- Rentals with pools Chicago
- Rentals with a balcony Chicago
- Rentals with an EV charger Chicago
- Waterfront rentals Chicago
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- 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
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- The Field Museum
- Lincoln Park Zoo
- Six Flags Great America
- Promontory Point
- Museum of Science and Industry
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Splash Station
- Flossmoor Golf Club
- Villa Olivia
- Raging Waves Waterpark
- Moraine Hills State Park
- Lincoln Park
- Things to do Chicago
- Food and drink Chicago
- Entertainment Chicago
- Art and culture Chicago
- Wellness Chicago
- Tours Chicago
- Sightseeing Chicago
- Things to do Cook County
- Tours Cook County
- Food and drink Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Entertainment Cook County
- Wellness Cook County
- Things to do Illinois
- Wellness Illinois
- Art and culture Illinois
- Food and drink Illinois
- Entertainment Illinois
- Sightseeing Illinois
- Tours Illinois
- Things to do United States
- Sightseeing United States
- Tours United States
- Art and culture United States
- Food and drink United States
- Entertainment United States
- Nature and outdoors United States
- Sports activities United States
- Wellness United States