Photo by Meghan hernandez

Highland Park Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Highland Park

Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (357)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town
The Gem Museum Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is NT$6,593
NT$7,547 total
includes taxes & fees
Sep 29 - Sep 30
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is NT$2,637
NT$4,622 total
includes taxes & fees
Sep 29 - Sep 30
Wrigleyville Suites
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is NT$2,579
NT$7,705 total
includes taxes & fees
Oct 2 - Oct 3
Ground Floor Studios in Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster

River West, Third Floor Chicago by 747 Lofts

2.0 star property
9.0 out of 10, Wonderful, (16)
"Overall solid property, I will return."
The price is NT$4,802
NT$8,097 total
includes taxes & fees
Oct 9 - Oct 10
River West, Third Floor Chicago by 747 Lofts
At Home in Oak Park
Apartment, Private Bathroom | Terrace/patio

At Home in Oak Park

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
The price is NT$5,795
NT$9,594 total
includes taxes & fees
Oct 26 - Oct 27
At Home in Oak Park
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Park Hotel Reviews

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Staff was great, food & drinks are too."
Caris 2-night trip
Posted 23 hours ago
Hyatt Regency O'Hare Chicago

Find out more about Highland Park

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 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 6 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.