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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Top Holiday Rentals in Chicago

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (974)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ฿4,357
฿6,069 total
includes taxes & fees
25 Nov - 26 Nov
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (605)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (375)
"Great place to stay. Loved it!"
United States
Peter
The price is ฿6,911
฿8,840 total
includes taxes & fees
10 Nov - 11 Nov
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (399)
"Quite and low key spot"
United States
Shunica
The price is ฿3,287
฿3,858 total
includes taxes & fees
17 Nov - 18 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (251)
"Great stay. "
United States
Teresa
The price is ฿4,126
฿4,843 total
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (708)
"Location was nice."
United States
Juliet
The price is ฿4,126
฿4,843 total
includes taxes & fees
10 Nov - 11 Nov
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (370)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (217)
"This hotel is a 10 out of 10 for me! The hotel room was clean and the location was great. When I come back next year I’m definitely coming back here "
United States
Amonee
The Neighborhood Hotel-Little Italy
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (56)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
United States
Swastika
The price is ฿3,839
฿4,507 total
includes taxes & fees
11 Nov - 12 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (187)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is ฿3,563
฿4,183 total
includes taxes & fees
23 Nov - 24 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites
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 ฿5,030
฿5,905 total
includes taxes & fees
7 Nov - 8 Nov
Wrigleyville Suites
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"I enjoyed my stay! Thanks!"
United States
Jonathan
The price is ฿3,839
฿4,507 total
includes taxes & fees
17 Nov - 18 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is ฿8,091
฿12,855 total
includes taxes & fees
9 Nov - 10 Nov
Stylish Apartment near Chicago Downtown
Interior
Art Villa
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is ฿17,514
฿33,491 total
includes taxes & fees
20 Nov - 21 Nov
Art Villa
Free WiFi
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is ฿32,494
฿38,145 total
includes taxes & fees
7 Nov - 8 Nov
Chicago luxury home suites
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (21)
"This property is excellent!"
United States
Philip
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

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 Six Flags Great America, 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 acclaimed theatre scene. 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 1140 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 Grant Park 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 Navy Pier.

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.