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Check prices for these dates

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Top Holiday Rentals in Chicago

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, (574)
"Very great place to stay!"
United States
Edwin
Kasa Magnificent Mile Chicago
Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (961)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ฿4,439
฿6,174 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (369)
"Friendly staff and great amenities "
United States
Bryan
The price is ฿5,752
฿7,485 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, (385)
"Great stay!"
United States
Joe
The price is ฿3,601
฿4,227 total
includes taxes & fees
4 Nov - 5 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, (241)
"Great stay. "
United States
Teresa
The price is ฿4,439
฿5,210 total
includes taxes & fees
6 Nov - 7 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, (691)
"Location was nice."
United States
Juliet
The price is ฿4,159
฿4,883 total
includes taxes & fees
3 Nov - 4 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, (364)
"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, (211)
"Perfect location and area was wonderful."
United States
Thomas
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, (53)
"Place was in a great location close to good restaurants "
United States
Charles
The price is ฿4,159
฿4,883 total
includes taxes & fees
16 Nov - 17 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
United States
Dane
The price is ฿8,046
฿12,530 total
includes taxes & fees
26 Oct - 27 Oct
Kasa River North Chicago
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, (185)
"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 ฿3,880
฿4,555 total
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is ฿2,039
฿4,036 total
includes taxes & fees
21 Oct - 22 Oct
Wrigleyville Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is ฿6,536
฿11,335 total
includes taxes & fees
21 Oct - 22 Oct
Stylish Apartment near Chicago Downtown
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)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
The price is ฿5,222
฿6,130 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Property amenity
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
3.5 star property
7.6 out of 10, Good, (144)
"Very clean and affordable "
United States
Matthew
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio
Art Villa
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is ฿17,702
฿33,850 total
includes taxes & fees
24 Oct - 25 Oct
Art Villa
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, (20)
"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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned."
Stephanie 2-night trip
Posted 19 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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 1125 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.