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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,106 reviews)
"The kitchen was great and check-in was easy."
United States
Marshal
The price is ₹9,350
₹13,689 total
includes taxes & fees
19 Mar - 20 Mar
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (443 reviews)
"Great value, friendly staff"
United States
Marcus
The price is ₹12,657
₹17,139 total
includes taxes & fees
5 Apr - 6 Apr
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (186 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
The price is ₹12,815
₹22,641 total
includes taxes & fees
12 Apr - 13 Apr
Kasa River North Chicago
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Very nice place to stay at. "
United States
ANDRO
The price is ₹8,510
₹9,990 total
includes taxes & fees
18 Mar - 19 Mar
Wrigleyville Suites
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

Swissotel - Chicago

Swissotel - Chicago

4/10 Poor
"I was pretty upset as soon as we got there you can’t even walk to get to the door there were so many cars parked in the front super tight to get in. Once checking in there were 2 open people talking and I walked up to one of them and told me to wait for some other guys who was already helping someone . I didn’t understood why those two didn’t help. We waited a while until some lady acknowledge us. My 4 year old was getting impatient. We brought a swimming stuff as I was telling my 4 year old we will go to the pool now, the lady said there is no pool. This is false advertisement. I was looking for hotel only for my 3 years old as we were staying there for st Patrick day weekend. The beds were super small you can’t fit 2 people. I slept in one so did my husband we went to target to get an Air mattress for my 4 year old. We were suppose to be checking in Friday- Sunday . We left early By Saturday we were uncomfortable and frustrated. "
juan 2-night trip
Posted 1 hour ago
Swissotel - Chicago

Find out more about Chicago

Holiday Rentals in Chicago

Search for holiday rentals in Chicago on Expedia.co.uk! 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 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 945 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 Wrigley Field.

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.