Highland Park Holidays & Package Deals

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Highland Park Holiday

Our pick of the best Highland Park Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

NZ$372

13 Oct - 14 Oct

includes taxes & fees

8/10 Very good! (2,291 reviews)

"Great location"

Reviewed on 21 Sept 2026

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

NZ$370

4 Oct - 5 Oct

includes taxes & fees

Marriott Chicago O'Hare

8535 West Higgins Road Chicago IL

Fully refundableReserve now, pay when you stay

NZ$367

16 Oct - 17 Oct

includes taxes & fees

8.6/10 Excellent! (1,399 reviews)

"Ray was a huge help and excellent customer services. We decided to take our first short baecation together and this was perfect! To new found love!Good job Ray!!! We will return."

Reviewed on 20 Sept 2026

See all 2,585 properties in Highland 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.

Stay near popular Highland Park attractions

Ravinia Park

8.4/10 (5 reviews)

Ravinia Park hosts North America's oldest outdoor music festival in a picturesque setting. Enjoy performances while picnicking on the lawn, with the Chicago Symphony Orchestra often featured during summer evenings.

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Ravinia Pavilion

9.6/10 (7 reviews)

Ravinia Pavilion hosts classical, jazz, and pop performances in a park-like setting. Enjoy concerts from covered seats or bring a gourmet picnic for the expansive lawn experience.

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What to do in Highland Park

360 CHICAGO Observation Deck

NZ$45

per adult

86% of travellers recommend

Art Institute of Chicago

NZ$67

per adult

92% of travellers recommend

Flyover in Chicago

NZ$47

per adult

98% of travellers recommend

See all activities in Highland Park

Frequently asked questions

How much does a Highland Park holiday package cost?

You'll find cheap prices on Expedia for your Highland Park escape. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday to Highland Park costs.

What are the cheapest months to go to Highland Park?

If you'd like to score a cheap Highland Park holiday package, consider visiting in December, January and February. You're likely to find lower rates on hotels and flights during these months — perfect for a budget-friendly getaway.

How many days is enough for Highland Park?

We'd suggest booking a Highland Park holiday for a minimum of 2 days. This will give you plenty of time to visit top sights including Ravinia Park and Highland Park Country Club, as well as explore neighbourhoods like Riverwoods and Bannockburn. You might even be able to make time for a day trip or two from Highland Park.

Is it worth booking a holiday package to Highland Park?

Whether you're looking to check out major sights like Chicago Botanic Garden and Ravinia Pavilion on your Highland Park holiday, or coming for its great shopping, golfing and dining, there's something for everyone here. With so much to experience, you'll soon find out why so many families think Highland Park is a good holiday destination.

How to find the best Highland Park package deals?

Start your search for a Highland Park package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Highland Park package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Highland Park adventure underway.

Is it cheaper to book a Highland Park holiday as a package?

You can enjoy significant savings on your Highland Park escape by booking a personalised holiday package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a holiday package to Highland Park?

Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Highland Park break.

How to plan a trip to Highland Park?

Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Highland Park.
Budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Highland Park.
Decide how long to go for: Now that you know more about Highland Park, you can work out the right length of your holiday. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customised Highland Park holiday package.

Explore a world of travel with Expedia

Highland Park Holiday Rentals

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Highland Park Holidays

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Plan, book, travel with confidence

Better together

Find the right fit

Rest easy