A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chicago vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,391 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is NT$4,652
NT$5,460 total
includes taxes & fees
Nov 23 - Nov 24
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (76 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
The price is NT$5,230
NT$8,149 total
includes taxes & fees
Nov 4 - Nov 5
Kasa Lake Shore Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (48 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is NT$4,839
NT$5,681 total
includes taxes & fees
Oct 29 - Oct 30
Wrigleyville Suites
A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (551 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NT$5,169
NT$6,872 total
includes taxes & fees
Nov 1 - Nov 2
Level Chicago – Old Town
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

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

8/10 Good
"The hotel didn’t meet my expectations for the view, but it definitely had one of the best locations. The location was absolutely unbeatable, with easy walking access to Millennium Park, the Chicago Riverwalk, the Chicago Theatre, Art institute of Chicago and many other downtown attractions. It made exploring the city on foot incredibly convenient and enjoyable. The room was comfortable, and the overall atmosphere had a distinctive character. I especially appreciated being able to reach so many of Chicago’s highlights without having to rely on transportation. My only disappointment was the view, which fell short of what I had hoped for. However, the hotel’s prime location made up for much of that disappointment. Overall, it was a convenient and enjoyable place to stay for a few days in Chicago. I would recommend it to travelers who prioritize location and easy access to the city’s main attractions over a spectacular room view."
Myung 3-night trip
Posted 5 hours ago
Sports Illustrated Resorts Chicago

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!

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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 933 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 Soldier Field 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.