Chicago Vacation Rentals
Search over 1 million properties and 550 airlines worldwide
Save 10% or more on select stays with Expedia Rewards
Most hotels are fully refundable. Because flexibility matters.
Check prices on Vacation Homes in Chicago
Browse Select Chicago Vacation Homes
Forest Park, IL
Situated in Forest Park, this vacation home is 1 mi (1.7 km) from Frank Lloyd Wright Home and Studio and within 6 mi (10 km) of Brookfield Zoo and Garfield Park ...
4.9/5 Exceptional! (17 reviews)
Coming home
"After living in the Oak Park/Forest Park area for 18 years, a friend and I moved to different parts of the country. We reconnected this weekend, and we had a lovely, comfortable home to reunite!"
Reviewed on Nov. 15, 2021
Get rates
Situated in Oak Park, this vacation home is 1.4 mi (2.2 km) from Frank Lloyd Wright Home and Studio and within 6 mi (10 km) of United Center and Humboldt Park. ...
5/5 Exceptional! (8 reviews)
Great experience in Oak Park area!
"Ali was a very helpful host, accurate listing and directions for checking in and out. Everything was clean and organized, good decor. Parking spot was a bit cramped because of garbage can being right next to spot. Otherwise a good experience"
Reviewed on Nov. 19, 2021
Hoffman Estates, IL
Situated in a rural location, this romantic vacation home is within 3 mi (5 km) of Schaumburg Medieval Times, Advocate Health Care, and Bridges of Poplar Creek ...
5/5 Exceptional! (2 reviews)
A memorable weekend!
"Lovely and warm home decorated beautifully. The homeowners thought of everything to make you feel at home even down to providing robes and slippers for the hot tub. We were blessed to of met the owners and we will surely be back. Gracias J&E!"
Reviewed on Nov. 17, 2021
Get rates
You could be seeing lower prices
With member prices, you could save 10% or more right now on thousands of properties.
Situated in the suburbs, this vacation home is 2.3 mi (3.7 km) from Ravisloe Country Club and within 6 mi (10 km) of Coyote Run Golf Course and Midwest Carvers ...
5/5 Exceptional! (1 review)
The Best place on earth!
"This house was perfect! Everything needed was supplied! Clean and with great stuff! I Loved my host and his attention was great! Quick responses and daily check in’s. I will surly return!"
Reviewed on Nov. 5, 2021
Get rates
This family-friendly Worth vacation home is located in a rural location, within 2 mi (3 km) of Water's Edge Golf Club and Lake Katherine Nature Center. Chicago ...
Hoffman Estates, IL
Located in Hoffman Estates, this family-friendly vacation home is 1.9 mi (3.1 km) from NOW Arena, and within 6 mi (10 km) of Santa's Village and Grand Victoria ...
4.9/5 Exceptional! (7 reviews)
Mecum car auction
"The house was perfect and communication with the owner was great"
Reviewed on Oct. 24, 2021
Lake Zurich, IL
Situated in Lake Zurich, this vacation home is within 6 mi (10 km) of Lakeview Beach and Dock, Bristol Trails Park, and Oak Ridge Marsh Nature Park. Breezewald ...
3/5 (2 reviews)
Beyond disappointed
"Honestly this house was full of bugs, the air conditioning didn’t work. While the property is very nice, the house is a bit run down. Things that bothered me the most. The owner has control of all the features, AC, Cable TV, etc.... The AC never worked properly and the house never got cooler than ..."
Reviewed on Jul. 4, 2020
Get rates
Mundelein, IL
Located in Mundelein, this family-friendly vacation home is 2.7 mi (4.3 km) from Lakeview Beach and Dock, and within 6 mi (10 km) of Lake County Fairgrounds ...
4.9/5 Exceptional! (29 reviews)
Cozy gome
"Was in a great location and accessible. Didn’t use the restroom in the basement, but upstairs one was really nice. Fridge is just located behind a door right outside the kitchen as u head down to the basement. Was clean and comfortable."
Reviewed on Nov. 6, 2021
Get rates
Berwyn, IL
Set in the center of Berwyn, this family-friendly vacation home is 3 mi (4.9 km) from Brookfield Zoo, and within 6 mi (10 km) of Douglas Park and Frank Lloyd ...
Get rates
Evanston, IL
Located in the heart of Evanston, this vacation home is 1.1 mi (1.8 km) from Northwestern University and 1.4 mi (2.3 km) from Lake Michigan. Ryan Field and Baha'i ...
Get rates
Glendale Heights, IL
Situated in Glendale Heights, this vacation home is within 2 mi (3 km) of Adventist GlenOaks Hospital, AMITA Health Medical Center, and Mediplus USA. Wheaton ...
Get rates
Located in Oak Park, this family-friendly vacation home is 0.3 mi (0.5 km) from Frank Lloyd Wright Home and Studio, and within 6 mi (10 km) of Garfield Park ...
Get rates
Oak Park, IL
Located in Oak Park, this family-friendly vacation home is 1.4 mi (2.2 km) from Frank Lloyd Wright Home and Studio, and within 6 mi (10 km) of Garfield Park ...
4.5/5 Wonderful! (6 reviews)
Great location, cute apartment
"We enjoyed our time at the apartment. It's located conveniently to all that Oak Park has to offer, and close to the green line and I-290 to get into Chicago. Host left us a very nice welcome amenity, and was responsive to a couple of minor requests we made."
Reviewed on Nov. 1, 2021
Get rates
Libertyville, IL
Situated in Libertyville, this vacation home is within 1 mi (2 km) of MainStreet Libertyville and Advocate Condell Child Day Center. Lambs Farm and Cuneo Mansion ...
4/5 Very Good! (2 reviews)
AC
"It was very hot and humid. One bedroom had no AC. Downstairs unit not cool enough. So one family member had very uncomfortable hot bedroom. More bed pillows needed."
Reviewed on Oct. 14, 2021
Get rates
Located in Austin, this vacation home is 2 mi (3.2 km) from Frank Lloyd Wright Home and Studio and within 6 mi (10 km) of United Center and Humboldt Park. Douglas ...
4.5/5 Wonderful! (4 reviews)
Fun in Chicago
"Had a great visit to Chicago with my wife and three teenage girls. The location was perfect. Easy walk to the "L" Austin station for a straight shot into the Loop. Also very close to Oak Park for restaurants, Frank Lloyd Wright, and other attractions. Apartment was as advertised. The 3 bedroom unit ..."
Reviewed on Apr. 22, 2019
Get rates
Evanston, IL
Situated in Evanston, this vacation home is within 1 mi (2 km) of Ryan Field and Northwestern University. Lake Michigan is 1.6 mi (2.6 km) away. Noyes Station ...
5/5 Exceptional! (1 review)
One of the best rentals ever
"Sarah was amazing, we have stayed at multiple listings in evanston and this was our favorite. Nice, clean, extra little amenities. Charming and lovely. We will definitely be back. Definitely one of the best!!! The personal attention from Sarah was all the difference."
Reviewed on Oct. 18, 2021
Get rates
Evanston, IL
Situated in Evanston, this vacation home is within 3 mi (5 km) of Lake Michigan, Northwestern University, and Loyola University Chicago. Wrigley Field and Lincoln ...
Get rates
Willow Springs, IL
Located in the heart of Willow Springs, this vacation home is within 6 mi (10 km) of Burr Ridge Village Center, SeatGeek Stadium, and Southwest Medical Consultants. ...
5/5 Exceptional! (1 review)
WONDERFUL stay on the outskirts of Chicago
"Tira’s home was excellently accommodated, very clean, and was a great location. The townhome is just down the road from a nice Italian restaurant and driving distance to local restaurants, bars, and coffee houses. The house was just as described with a ton of room including a garage we could use. ..."
Reviewed on Sep. 29, 2021
Get rates
Winnetka, IL
Situated in Winnetka, this vacation home is 0.6 mi (1 km) from Lake Michigan and within 6 mi (10 km) of Northwestern University and Chicago Botanic Garden. Baha'i ...
Get rates
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other property types in Chicago
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St, Chicago, IL
4.2/5 Excellent! (1,705 reviews)
"Loved the comfortable bed. Wish is was free breakfast. Also it was up to date"
Reviewed on Nov. 28, 2021
The Whitehall Hotel
105 E Delaware Pl, Chicago, IL
3.9/5 Very Good! (3,392 reviews)
"Loved location and facility. Very nice and comfortable"
Reviewed on Nov. 27, 2021
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
4.6/5 Wonderful! (2,852 reviews)
"It was a wonderful experience all around staying at this property. Thank you!"
Reviewed on Nov. 26, 2021
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More trip options
- Popular Destinations
- More Accommodation Types in Chicago
- Be inspired: Top Vacation Homes destinations in 2021
- All Accommodation Types
- Expedia's Latest Trends
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
- Aparthotels
- Apartments
- B&B
- Cabin Rentals
- Castles
- Chalets
- Condo Rentals
- Condo Resorts
- Cottages
- Country Houses
- Cruise Ships
- Farmstay
- Guest Houses
- Holiday Park Resorts
- Hostels
- Houseboats
- Inns
- Lodges
- Motels
- Palaces
- Pensions
- Pousadas
- RV Parks
- Ranches
- Residences
- Resorts
- Riads
- Ryokans
- Safari Tentalow
- Townhomes
- Treehouses
- Vacation Homes
- Villas
Hotels
Hotels in SchaumburgHotels near Six Flags Great AmericaLakeview hotelsCheap Hotels in Downtown ChicagoMagnificent Mile hotelsHotels in RosemontHotels near Soldier FieldHotels in MarkhamHotels in NapervilleHotels near United CenterLincoln Park hotelsHotels near McCormick PlaceDowntown Chicago hotelsHotels in WinfieldHotels near Navy PierHotels near Grant ParkHotels in Elk Grove VillageHotels near Michigan AvenueDowntown Chicago 4 Star Star Hotels