Photo by Meghan hernandez

Search Holiday Rentals in Highland Park

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
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Top Holiday 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, (361)
"Great place to stay. Loved it!"
Level Chicago – Old Town
The Gem Museum Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized 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 5.677.780 ₫
6.499.751 ₫ total
includes taxes & fees
29 Oct - 30 Oct
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 2.377.350 ₫
4.111.523 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Wrigleyville Suites
Ground Floor Studios in Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster

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. "
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 3.567.610 ₫
6.220.733 ₫ total
includes taxes & fees
9 Oct - 10 Oct
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 3.894.730 ₫
7.018.961 ₫ total
includes taxes & fees
2 Nov - 3 Nov
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

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

10/10 Excellent
"The staff was very professional and helpful with inquiries. Would stay there again."
Shawn 4-night trip
Posted 14 hours ago
Hampton Inn Chicago-O'Hare International Airport

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.