Search Holiday Rentals in Chicago

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
1 Jan - 2 Jan
Tomorrow
2 Jan - 3 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Chicago holiday rentals

Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is Rp2.251.800
Rp2.643.388 total
includes taxes & fees
4 Jan - 5 Jan
Chicago luxury home suites
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1029)
"My favorite place to stay hands-down"
United States
Michele
The price is Rp1.829.104
Rp2.636.701 total
includes taxes & fees
5 Jan - 6 Jan
Sentral Michigan Avenue
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, (408)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
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
9.8 out of 10, Exceptional, (9)
"Good for family, enjoyed the stay"
United States
Karthik
The price is Rp14.951.952
Rp21.057.033 total
includes taxes & fees
5 Jan - 6 Jan
ENVITAE Hotel 4 Bedroom Luxury Apartments
Business centre
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
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

River Hotel

River Hotel

10/10 Excellent
"Not needed"
CARNITTA 1-night trip
Posted 1 day ago
River Hotel

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia.co.id! 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 holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Field Museum of Natural History, or you can select a more secluded option if you're looking for 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 holiday rentals are there in Chicago?

With 926 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.