Highland Park Holidays

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Top hotels in Highland Park

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 HK$1,407 per night from 8 Aug to 9 Aug
HK$1,407
HK$1,652 total
8 Aug - 9 Aug
includes taxes & fees
8/10 Very Good! (2,079 reviews)
Convenient location
"Excellent option when traveling from ORD. Convenient location with direct access to the airport terminal. Good facilities."

Reviewed on 13 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 HK$1,194 per night from 21 Jul to 22 Jul
HK$1,194
HK$1,361 total
21 Jul - 22 Jul
includes taxes & fees
8.6/10 Excellent! (1,735 reviews)
"Generally a very nice hotel. Escalators to lower level with not working all weekend making it difficult for people with mobility issues."

Reviewed on 15 Jul 2025

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 HK$261 per night from 28 Jul to 29 Jul
HK$261
HK$1,412 total
28 Jul - 29 Jul
includes taxes & fees
8.2/10 Very Good! (1,033 reviews)
Great experience expect the one thing
"Overall, we had a great experience. However, the valet service was quite expensive and the staff could have been more courteous. The self-service parking next door was also a bit confusing to navigate."

Reviewed on 14 Jul 2025

The Chicago Hotel Collection Ambassador Gold Coast
See all 2,511 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.

Popular places to visit

Grant Park

Grant Park

4.5/5(96 reviews)

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
Soldier Field featuring modern architecture, a city and a high-rise building

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Six Flags Great America showing rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Highland Park

River tour boat in Chicago

Architecture River Tour

HK$383
per adult
94% of travellers recommend
Architecture River Tour
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

HK$235
per adult
84% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

HK$1,115
per adult
92% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
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.