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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Chicago holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ฿3,717
฿5,287 total
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (650)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (389)
"Would certainly stay again. The business center was an unexpected bonus, along with the great view. "
Canada
Mark
Kasa South Loop Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
7.4 out of 10, Good, (3)
"Do not book. This is a scam you will be asking to zelle a several hundred dollar security deposit after paying in full and before check in. You’ll receive sketchy FaceTime audio calls and messages from several different numbers requesting this. "
United States
Brooke
The price is ฿3,400
฿3,991 total
includes taxes & fees
18 Dec - 19 Dec
Chicago luxury home suites
Property entrance
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (225)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ฿3,655
฿4,290 total
includes taxes & fees
18 Dec - 19 Dec
Wrigleyville Suites
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

Stylish Apartment near Chicago Downtown
2.0 star property
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
Art Villa
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
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.
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Top Chicago Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Friendly/Helpful staff made for a great welcome! "
Lisa 2-night trip
Posted 4 hours ago
Crowne Plaza Chicago West Loop by IHG

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 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 923 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.