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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Top Holiday Rentals in Highland Park

Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (369)
"Friendly staff and great amenities "
United States
Bryan
The price is ฿5,752
฿7,485 total
includes taxes & fees
10 Nov - 11 Nov
Level Chicago – Old Town
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher
The Gem Museum Suites
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (91)
"Super nice hotel and staff "
United States
EMILY
The price is ฿6,362
฿7,283 total
includes taxes & fees
18 Nov - 19 Nov
The Gem Museum Suites
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is ฿2,039
฿4,036 total
includes taxes & fees
22 Oct - 23 Oct
Wrigleyville Suites
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is ฿2,909
฿5,692 total
includes taxes & fees
23 Oct - 24 Oct
River West, Third Floor Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (20)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
Apartment, Private Bathroom | Terrace/patio
At Home in Oak Park
At Home in Oak Park
3.5 star property
9.4 out of 10, Exceptional, (8)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
The price is ฿4,806
฿8,662 total
includes taxes & fees
4 Nov - 5 Nov
At Home in Oak Park
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior
Historic Oak Park Residence
Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
The price is ฿4,534
฿8,808 total
includes taxes & fees
4 Nov - 5 Nov
Historic Oak Park Residence
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior
Historic Oak Park Home
Historic Oak Park Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ฿4,534
฿8,808 total
includes taxes & fees
4 Nov - 5 Nov
Historic Oak Park Home
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Nice"
grecia 1-night trip
Posted 1 day ago
Hyatt Regency O'Hare Chicago

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:

  • View our selection of featured holiday rentals in Highland Park
  • Use the map to find apartments and other holiday homes in the Highland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland Park while they last

Look no further and take a look at our great range of rental properties in Highland Park!

Frequently asked questions

Are there holiday rentals in Highland Park?

Yes, we give you a choice of holiday rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. The shops and live music are just a few reasons why travellers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

How many holiday rentals are there in Highland Park?

With 5 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Highland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Park. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.