Highland Park Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Flight + Hotel Deals in Highland Park
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
€1,460
per person
19 Nov - 23 Nov
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on 12 Oct 2026
Hotel Riu Plaza Chicago
Downtown Chicago
€1,079
per person
19 Nov - 23 Nov
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Cet hôtel est tout simplement parfait. Tout est d'une propreté irréprochable, le buffet du matin compris dans le prix de la chambre est exceptionnel et varie tous les jours, Et que dire de l'emplacement, tout simplement idéal, au coeur de Chicago, au coin de selon moi la plus belle rue de Chicago le Michigan Avenue, à deux pas de la Chicago River. Je vous conseille fortement de faire le tour de bateau Architecture sur la rivière, c'est vraiment intéressant et ça va donnes une vue complètement différente de la ville. Chicago a été un énorme coup de cœur pour moi. Le seul bémol est que si vous y allez en vacances, mois ce fut pour affaire, prévoyez un budget car c'est assez dispendieux.
Reviewed on 12 Oct 2026
Top hotels in Highland Park
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€152
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,481 reviews)
"Good location"
Reviewed on 12 Oct 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€239
7 Nov - 8 Nov
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
€163
23 Oct - 24 Oct
includes taxes & fees
9/10 Wonderful! (3,255 reviews)
"Airport shuttle was nice."
Reviewed on 12 Oct 2026
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.
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.
Ravinia Pavilion
9.6/10 (7 reviews)
Ravinia Pavilion hosts classical, jazz, and pop performances in a park-like setting. Enjoy concerts from covered seats or bring a gourmet picnic for the expansive lawn experience.
What to do in Highland Park
Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
Frequently asked questions
How much does a Highland Park holiday package cost?
You'll find cheap prices from €849 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?
- 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.
- 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.
- 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.
- 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.
