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.

Browse Select Chicago Vacation Homes

Updated Forest Park 3 BR Bungalow
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
Updated Forest Park 3 BR Bungalow
✅Stylish 2BDR, ✅For Families ✅ Parking, ✅Laundry, Great for comfy long stays.
The price is CA $207 per night from Dec 26 to Dec 26
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

✅Stylish 2BDR, ✅For Families ✅ Parking, ✅Laundry, Great for comfy long stays.
"The Estates" 2 Comfy Rooms in our Home, Hot Tub/Office Space & More
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
"The Estates" 2 Comfy Rooms in our Home, Hot Tub/Office Space & More
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
NEW! Spacious Family Glenwood Estates Home w/ Pool
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
NEW! Spacious Family Glenwood Estates Home w/ Pool
The Comfy King Ranch /King Bed/Fast WiFi/Free Pkg
The price is CA $211 per night from Nov 30 to Nov 30
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 ...
The Comfy King Ranch /King Bed/Fast WiFi/Free Pkg
House in Hoffman Woods - KILLER views + 1GB WIFI
The price is CA $510 per night from Dec 6 to Dec 6
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

House in Hoffman Woods - KILLER views + 1GB WIFI
Beautiful Eco Friendly Tudor Castle on 1 acre
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
Beautiful Eco Friendly Tudor Castle on 1 acre
Quaint Bungalow, near Great Lakes Naval Base
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
Quaint Bungalow, near Great Lakes Naval Base
5 Star Large Plush Home 4 Bedroom
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
5 Star Large Plush Home 4 Bedroom
Sunny 2 Bedroom in Charming Evanston
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
Sunny 2 Bedroom in Charming Evanston
NEW! Glendale Heights Home w/ Office & Backyard!
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
NEW! Glendale Heights Home w/ Office & Backyard!
NEW! Classic Oak Park Home, 11 Mi to Dtwn Chicago!
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
NEW! Classic Oak Park Home, 11 Mi to Dtwn Chicago!
Vintage Greystone in historic Oak Park,
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
Vintage Greystone in historic Oak Park,
2 Bdr House ★ WiFi ★ Ideal refuge during the crisis
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
2 Bdr House ★ WiFi ★ Ideal refuge during the crisis
SPECIAL OFFER - STUNNING,SPA SEXY SUITE EASY COMMUTE PRIVATE FREE pgk  greatdeal
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
SPECIAL OFFER - STUNNING,SPA SEXY SUITE EASY COMMUTE PRIVATE FREE pgk greatdeal
Modern Luxury 3 bd Home min from NU & Lake Mich
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
Modern Luxury 3 bd Home min from NU & Lake Mich
Duplex Down
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
Duplex Down
Classy and Sophisticated Townhome in quiet area
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
Classy and Sophisticated Townhome in quiet area
Warm and Cheerful 3 Bedroom Winnetka Townhouse
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
Warm and Cheerful 3 Bedroom Winnetka Townhouse
Single family house... 1 mile to downtown Glen Ellyn
Don't see what you're looking for?
See all available properties in Chicago
View all properties
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

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St, Chicago, IL
The price is CA $137 per night from Dec 5 to Dec 5
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

DoubleTree by Hilton Chicago - Magnificent Mile
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL
The price is CA $108 per night from Dec 16 to Dec 16
3.9/5 Very Good! (3,392 reviews)
"Loved location and facility. Very nice and comfortable"

Reviewed on Nov. 27, 2021

The Whitehall Hotel
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive, Chicago, IL
The price is CA $134 per night from Dec 19 to Dec 19
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

LondonHouse Chicago, Curio Collection by Hilton
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