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
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Chicago holiday rentals

Indoor pool

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,235 reviews)
"Great property and location."
United States
Michael
The price is 3.975.955 ₫
5.439.095 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (512 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is 7.661.537 ₫
9.642.599 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (9 reviews)
"Great location and super clean!"
United States
Erica
The price is 8.230.648 ₫
11.348.582 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Kasa Lake Shore Chicago
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

Omni Chicago Hotel

Omni Chicago Hotel

10/10 Excellent
"Great location"
Melissa 1-night trip
Posted 7 hours ago
Omni Chicago Hotel

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 art 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 928 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 Wrigley Field and Michigan Avenue.

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.