Chicago Vacation Rentals

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Check prices for these dates

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

Our top choices for Chicago vacation rentals

Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,106 reviews)
"The kitchen was great and check-in was easy."
United States
Marshal
The price is NT$3,511
NT$5,062 total
includes taxes & fees
Mar 18 - Mar 19
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (443 reviews)
"Great value, friendly staff"
United States
Marcus
The price is NT$6,904
NT$8,895 total
includes taxes & fees
Apr 17 - Apr 18
Level Chicago – Old Town
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
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 NT$5,100
NT$8,994 total
includes taxes & fees
Mar 25 - Mar 26
Kasa River North Chicago
Living area

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.2 out of 10, Wonderful, (29 reviews)
"Very nice place to stay at. "
United States
ANDRO
The price is NT$3,170
NT$3,721 total
includes taxes & fees
Mar 18 - Mar 19
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 4 hours ago
Swissotel - 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
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  • 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 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 vacation rentals are there in Chicago?

With 945 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 Wrigley Field.

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.