Highland Park Vacations

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    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Highland Park Vacation Packages

Highland Park Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 694 per night from Aug 6 to Aug 7
AEDĀ 694
AEDĀ 791 total
6 Aug - 7 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 675 per night from Jul 19 to Jul 20
AEDĀ 675
AEDĀ 803 total
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very Good! (1,769 reviews)
"The room we had there was dog pee spots all over the carpet and the room smelled. There werenā€™t any light bulbs in the lamps. The hallway smelled like mold and mildew. I will not stay there again ever."

Reviewed on 17 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 1,025 per night from Aug 7 to Aug 8
AEDĀ 1,025
AEDĀ 1,203 total
7 Aug - 8 Aug
includes taxes & fees
8.4/10 Very Good! (2,344 reviews)
"The room was amazingly quiet for being right at the airport. The restaurant was great; the food was very good. We watched the soccer game in the lounge. Great service there as well."

Reviewed on 17 July 2026

Hilton Chicago O'Hare Airport
See all 2,561 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.
See properties

Frequently asked questions

How much does a Highland Park vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Highland Park costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Highland Park?
If you're looking to book a cheap Highland Park vacation package, consider planning a trip in December, January and February. You'll generally find better rates on flights and hotels during these months ā€” perfect for a budget-friendly getaway.
How to find the best Highland Park package deals?
Start your search for a Highland Park package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Highland Park package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Highland Park escape underway.
Is it cheaper to book a Highland Park vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Highland Park vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Highland Park?
If you're considering a spontaneous Highland Park vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Highland Park?

  1. Choose your travel dates: The things you'd like to do in Highland Park and your favorite season can help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Highland Park.
  3. Decide your trip length: Think about how much time you want to spend exploring Highland Park. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the perfect Highland Park vacation package for you.