Highland Park Vacations

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Find the Best Highland Park Vacation Packages

Highland Park Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NT$4,611
NT$5,481 total
Aug 11 - Aug 12
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
NT$6,808
NT$7,991 total
Aug 29 - Aug 30
includes taxes & fees
8.4/10 Very Good! (2,373 reviews)
"Comfortable hotel in the airport. Staff is friendly and professional. Restaurant and bar were super congenial. Great place to stay on a quick trip to Chicago or on layover."

Reviewed on 2026/8/6

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
NT$5,459
NT$6,223 total
Aug 30 - Aug 31
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 2,576 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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Frequently asked questions

How much does a Highland Park vacation 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 vacation to Highland Park costs.
What are the cheapest months to go to Highland Park?
If you'd like to score a cheap Highland Park vacation 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 vacation 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 neighborhoods 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 vacation package to Highland Park?
Whether you're looking to check out major sights like Chicago Botanic Garden and Ravinia Pavilion on your Highland Park vacation, 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 vacation 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 vacation as a package?
You can enjoy significant savings on your Highland Park escape by booking a personalized vacation 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 vacation 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?
  1. 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.
  2. 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.
  3. Decide how long to go for: Now that you know more about Highland Park, you can work out the right length of your vacation. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Highland Park vacation package.

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