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

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$3,804 per night from Nov 10 to Nov 11
NT$3,804
NT$4,523 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very Good! (2,658 reviews)
"Amazing stay, great amenities, breakfast was good had a lot of options. Area was nice and not to far from train services to get to Chicago."

Reviewed on 2026/11/5

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 NT$6,664 per night from Nov 27 to Nov 28
NT$6,664
NT$7,823 total
Nov 27 - Nov 28
includes taxes & fees
8.6/10 Excellent! (2,589 reviews)
"Hotel needs spiffing"

Reviewed on 2026/11/4

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,694 per night from Nov 25 to Nov 26
NT$4,694
NT$5,511 total
Nov 25 - Nov 26
includes taxes & fees
Marriott Chicago O'Hare
See all 2,681 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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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.