Highland Park Holidays from AU$2,499

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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.

The Latest Highland Park Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$2,874, price is now AU$2,499 per person
AU$2,499
per person
2 Sept - 5 Sept
found 3 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$3,374, price is now AU$2,723 per person
AU$2,723
per person
2 Sept - 5 Sept
found 3 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Property was clean. Upon check in my room had not been properly cleaned however once the front desk was made aware it was corrected. The staff was friendly and helpful.

Reviewed on 21 July 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,445, price is now AU$2,787 per person
AU$2,787
per person
2 Sept - 5 Sept
found 3 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,307, price is now AU$2,772 per person
AU$2,772
per person
2 Sept - 5 Sept
found 3 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent.

Reviewed on 20 July 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$3,810, price is now AU$3,251 per person
AU$3,251
per person
2 Sept - 5 Sept
found 3 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)

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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is AU$308 per night from 6 Aug to 7 Aug
AU$308
6 Aug - 7 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
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 AU$296 per night from 26 July to 27 July
AU$296
26 July - 27 July
includes taxes & fees
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 AU$398 per night from 16 Aug to 17 Aug
AU$398
16 Aug - 17 Aug
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 2,561 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

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.
See properties

What to do in Highland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$39
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

AU$82
per adult
98% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
See all activities in Highland Park

Frequently asked questions

How much does a Highland Park holiday package cost?
You'll find cheap prices from AU$2,499 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.