Chicago Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 13 - Dec 14
Tomorrow
Dec 14 - Dec 15
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Chicago vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1007)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is NT$3,686
NT$5,242 total
includes taxes & fees
Dec 21 - Dec 22
Sentral Michigan Avenue
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is NT$4,211
NT$4,944 total
includes taxes & fees
Dec 14 - Dec 15
Chicago luxury home suites
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (399)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
Business center
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is NT$28,776
NT$40,335 total
includes taxes & fees
Dec 18 - Dec 19
ENVITAE Hotel 4 Bedroom Luxury Apartments
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Always dependable for a comfortable stay. "
jennifer 3-night trip
Posted 21 hours ago
Palmer House a Hilton Hotel

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Chicago
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

Look no further and take a look at our great range of rental properties in Chicago!

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Field Museum of Natural History, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and entertainment choices. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many vacation rentals are there in Chicago?

With 923 Expedia vacation rentals, you're sure to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Lake Michigan are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Michigan Avenue and Wrigley Field.

What are vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.