Highland Park Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NT$5,067 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Highland Park Vacation Packages

Highland Park Hotel Deals

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$5,530 per night from Jul 26 to Jul 27
NT$5,530
NT$6,492 total
Jul 26 - Jul 27
includes taxes & fees
8/10 Very Good! (2,048 reviews)
"Convenient to airport after flight got cancelled not once but twice ."

Reviewed on 2025/7/2

Hilton Chicago O'Hare Airport
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$54 per night from Jul 6 to Jul 7
NT$54
NT$4,135 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Great location and decent rooms. I had a strange experience in that two days in to my four day stay management ( dressed in plain, casual clothes of shorts and tshirt) came to my door and told me I wasn’t supposed to be in my room; that my room was supposed to be vacant. I would have questioned wether ..."

Reviewed on 2025/7/2

The Chicago Hotel Collection Ambassador Gold Coast
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 NT$4,772 per night from Aug 5 to Aug 6
NT$4,772
NT$5,440 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (1,700 reviews)
"I like it because I get to relax"

Reviewed on 2025/7/4

Hyatt Regency O'Hare Chicago
See all 2,484 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

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

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

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.