Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Highland Park vacation rentals

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (464 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is NT$5,487
NT$7,226 total
includes taxes & fees
Apr 16 - Apr 17
Level Chicago – Old Town
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (111 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is NT$7,014
NT$8,030 total
includes taxes & fees
Apr 26 - Apr 27
The Gem Museum Suites
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (34 reviews)
"Great location and space ! Will use again "
United States
Vanessa
The price is NT$3,436
NT$4,033 total
includes taxes & fees
Apr 15 - Apr 16
Wrigleyville Suites
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is NT$8,133
NT$12,842 total
includes taxes & fees
Apr 15 - Apr 16
Historic Oak Park Residence
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NT$6,841
NT$11,363 total
includes taxes & fees
Apr 20 - Apr 21
Historic Oak Park Home
Interior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "
United States
Paul
The price is NT$3,841
NT$13,654 total
includes taxes & fees
Apr 23 - Apr 24
River West, Third Floor Chicago by 747 Lofts
Studio | Living area

Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (13 reviews)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is NT$4,260
NT$10,112 total
includes taxes & fees
Apr 17 - Apr 18
Chicago Second Floor Studio by 747 Lofts
Studio | Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (21 reviews)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
United States
Susan
The price is NT$5,400
NT$12,078 total
includes taxes & fees
May 4 - May 5
Ground Floor Studios in Chicago by 747 Lofts
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 Highland Park Hotel Reviews

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

8/10 Good
"The hotel overall was good. The only 2 drawbacks I noticed was the restaurant and the bathroom. The restaurant was limited in what they offer, was too pricey for what they offer, and some of the fruit in the breakfast buffet was not so fresh. The bathroom was clean, but the layout wasn't good. The TP was well behind you. Which in itself is not a big deal. But if you have a bad back, it can difficult to grab some from the roll. There was no venting fan. So the mirrors took forever to unfog. Also, the door only opened to a 90° angle. A couple of times I got done brushing my teeth, turned to leave, and bumped into the end of the door. None of the bathroom items are a big deal. But if you're someone who is on the bigger side, is a bit handicapped, or needs to get ready in a hurry, there may be better options. "
Christopher 4-night trip
Posted 1 hour ago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Find out more about Highland Park

Search for holiday rentals in Highland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Park using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Highland Park?

Yes, there are vacation rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more secluded option if you want a quieter place to stay. The shops and live music are just a few reasons why travelers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

How many vacation rentals are there in Highland Park?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Highland Park stay.

What can I see and do in Highland Park?

Enjoy the outdoors at Lake Michigan and Chicago Botanic Garden, or simply take in cultural attractions like Ravinia Park and Ravinia Pavilion. Other popular places to visit in the area include Naval Base Great Lakes and Wrigley Field.

What are vacation rentals like in Highland Park?

Vacation rentals are privately owned properties you can stay in for several days or more in Highland Park. Vacation rentals feature amenities like kitchens and laundry facilities 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 privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.