Chicago Vacation Rentals

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Oct 23 - Oct 24
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Vacation Rentals in Chicago

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (962)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is NT$4,122
NT$5,741 total
includes taxes & fees
Nov 10 - Nov 11
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, (370)
"Friendly staff and great amenities "
United States
Bryan
The price is NT$6,271
NT$8,048 total
includes taxes & fees
Nov 11 - Nov 12
Level Chicago – Old Town
Business center
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (174)
"This place has everything for a multi-night stay."
United States
Dane
Kasa River North Chicago
Fridge, microwave, oven, stovetop
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
The price is NT$30,740
NT$36,086 total
includes taxes & fees
Nov 3 - Nov 4
Chicago luxury home suites
Superior Apartment, City View | Living area | 75-inch Smart TV with digital channels, Netflix, streaming services
4BR Corporate Suite Central and Modern
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (4)
"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$4,317
NT$11,526 total
includes taxes & fees
Oct 29 - Oct 30
4BR Corporate Suite Central and Modern
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, (54)
"Place was in a great location close to good restaurants "
United States
Charles
The price is NT$3,632
NT$4,264 total
includes taxes & fees
Nov 5 - Nov 6
Sonder by Marriott Bonvoy The Opal Apartments River North
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, (243)
"Great stay. "
United States
Teresa
The price is NT$4,144
NT$4,864 total
includes taxes & fees
Nov 13 - Nov 14
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great place to stay in the city!!! The room was super nice with an amazing city view and the end was just perfect !!! Housekeeping staff was outstanding and it was in a very downtown convenient area to walk and find everything around !!! Would come back for sure 10000%"
andrea 6-night trip
Posted 12 hours ago
Hilton Chicago/Magnificent Mile Suites

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 Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed theater scene. 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 1125 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 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 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.