Highland Park Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Save up to NT$5,067 when you book a flight and hotel together*
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Find the Best Highland Park Vacation Packages

Highland Park Hotel Deals

Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$3,274 per night from Aug 26 to Aug 27
NT$3,274
NT$4,741 total
Aug 26 - Aug 27
includes taxes & fees
8.8/10 Excellent! (1,323 reviews)
"Good"

Reviewed on 2025/8/22

Claridge House
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$4,650 per night from Sep 19 to Sep 20
NT$4,650
NT$5,459 total
Sep 19 - Sep 20
includes taxes & fees
8.4/10 Very Good! (1,130 reviews)
"It was very nice!!!!"

Reviewed on 2025/8/25

Marriott Chicago O'Hare
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$5,480 per night from Sep 19 to Sep 20
NT$5,480
NT$6,433 total
Sep 19 - Sep 20
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
Passing Thru
"Nice quiet and convenient hotel and room. Excellent staff."

Reviewed on 2025/8/24

Hilton Chicago O'Hare Airport
See all 2,477 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.

Discover the most popular places to visit in Highland Park

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

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.

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