Highland Park Holidays

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Your Highland Park Holiday

When you organise a holiday package to Highland Park, you can relax and enjoy your getaway knowing that all your travel arrangements are under control. Uncover the many delights of this amazing city from your base in a neighbourhood like Riverwoods, which is good for nature. Every trip to Highland Park needs a well-thought-out itinerary. Fill yours with major attractions like Chicago Botanic Garden, Lake Forest College and Ravinia Park. A couple of quick clicks is all it takes to put together a tailored Highland Park holiday on Expedia.

Highland Park Holiday

Highland Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
29,700
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Marriott Theatre, North Shore Centre for the Performing Arts and Kohl Childrens Museum

Our pick of the best 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 AU$325 per night from 23 Aug to 24 Aug
AU$325
23 Aug - 24 Aug
includes taxes & fees
8/10 Very Good! (2,070 reviews)
US break
"Hotel is well run and organised, very friendly staff and superb facilities. Buffet breakfast excellent with really great staff notably Ali and Mohammed and Emma, aka Da Queen! Really easy access to Metro and onwards to City Centre. Front desk very helpful.Ricardo Delgado sorted out a late check out ..."

Reviewed on 30 Jul. 2025

Hilton Chicago O'Hare Airport
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 AU$238 per night from 21 Aug to 22 Aug
AU$238
21 Aug - 22 Aug
includes taxes & fees
8.6/10 Excellent! (1,802 reviews)
"Very clean and helpful staff"

Reviewed on 31 Jul. 2025

Hyatt Regency O'Hare Chicago
Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$289 per night from 12 Aug to 13 Aug
AU$289
12 Aug - 13 Aug
includes taxes & fees
8.8/10 Excellent! (1,290 reviews)
"The room was nice and the lobby is beautiful! Overall a great experience, staff was very friendly and acco"

Reviewed on 2 Aug. 2025

Claridge House
See all 2,572 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Highland Park

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Highland Park

River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

AU$46
per adult
92% of travellers recommend
Skyline Lake Tour
Chicago White Sox Baseball Game at Guaranteed Rate Field

Chicago White Sox Baseball Game at Guaranteed Rate Field

AU$31
per adult
Chicago White Sox Baseball Game at Guaranteed Rate Field
See all activities in Highland Park

Frequently asked questions

How much does a Highland Park holiday 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 holiday to Highland Park costs.
What are the cheapest months to go to Highland Park?
If you'd like to score a cheap Highland Park holiday 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 holiday 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 neighbourhoods 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 holiday package to Highland Park?
Whether you're looking to check out major sights like Chicago Botanic Garden and Ravinia Pavilion on your Highland Park holiday, 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 holiday 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 holiday as a package?
You can enjoy significant savings on your Highland Park escape by booking a personalised holiday 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 holiday 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 holiday. 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 customised Highland Park holiday package.

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