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

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chicago holiday 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, (1,409 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is Rp2.300.921
Rp2.701.050 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (86 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is Rp2.749.528
Rp4.344.215 total
includes taxes & fees
22 Nov - 23 Nov
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, (50 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is Rp2.686.216
Rp3.153.347 total
includes taxes & fees
10 Nov - 11 Nov
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, (559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is Rp3.109.572
Rp4.096.583 total
includes taxes & fees
23 Nov - 24 Nov
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Pros Location location location. Walking distance to everything Brrakfast available. Next door to Gotham bagels! Staff is kind Housekeeping is every three days. Room is outdated but works, Shower is very narrow, a/c is loud."
Kenji 3-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia.co.id! 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 933 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 Soldier Field 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.