Highland Park Holidays from £795
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Your Highland Park Holiday
Planning your next big adventure is a piece of cake with a Highland Park holiday package. The neighbourhood of Riverwoods, which is great for nature, makes a superb base to uncover the marvels of this unique city. If sightseeing is part of the plan during your trip to Highland Park, check out well-known attractions like Chicago Botanic Garden, Lake Forest College and Northbrook Sports Complex. Whoever you're escaping with and whatever you plan to spend, your dream Highland Park holiday is just clicks away with Expedia.
Top Highland Park Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£1,780
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.
Reviewed on 8 Aug 2026
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, Kohl Childrens Museum and North Shore Centre for the Performing Arts |
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
£126
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (1,957 reviews)
"nice environment"
Reviewed on 8 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£190
30 Aug - 31 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
£143
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (2,966 reviews)
"We got a double bed room which was great and spacious but it doesn’t have a kitchen type amenities."
Reviewed on 8 Aug 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
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
Frequently asked questions
How much does a Highland Park travel package cost?
The most affordable Highland Park travel package is £795, so your dream trip can become a reality — without spending a fortune. Bundle flights, hotels, car rentals and more to tailor make a package that suits you.
If I'm not able to travel, can I cancel my Highland Park travel package?
You can cancel your Highland Park booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
How do I get a cheap travel package to Highland Park?
If you love bargains, combine your bookings into a Highland Park travel package. Whether you need hotels, flights, rental cars or tours, you can book them all in one place. You'll have endless choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 properties worldwide to choose from. Fly with who you want, stay wherever you like and save a packet — now that's the perfect escape!
Does Expedia offer Book Now, Pay Later Highland Park holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book an incredible getaway without draining your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your trip. Check out these flexible payment options:
- Pay monthly holidays: Klarna offers easy monthly payment plans that suit all budgets, so you can escape on that well-earned holiday now.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
- Low deposit holidays: Hitting the "book now" button is much easier with this payment option. Simply put down a small deposit on your booking and then start packing your bags.
Where should I stay in Highland Park?
You'll want to stay where the action is. Many visitors like to book hotels in the vicinity of popular sights, like Chicago Botanic Garden, Highland Park Country Club and Ravinia Pavilion.
What are the top hotels in Highland Park?
Get your escape off to a fantastic start by staying at Hyatt Regency Chicago. It's one of most popular properties in Highland Park. Another cosy option is The Godfrey Hotel Chicago.
How far in advance should I book my Highland Park holiday?
You'll be rewarded with the widest variety and the cheapest prices by booking your holiday to Highland Park early. Air carriers generally advertise flight tickets around 12 months before departure, so start locking things in ASAP. Having said that, Expedia is committed to providing you with the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Highland Park travel package include?
It comes down to what you're looking for. If you're travelling solo, you might decide to bundle hotels and flights. Taking the whole crew to Highland Park? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking a Highland Park travel package?
A travel package can be cheaper than individually booking everything you need for your adventure. For example, combine your flights, hotels and rental cars and score big savings. Whatever type of holiday you have in mind, there's bound to be a package that suits your budget.
Can I choose my airline with a Highland Park Expedia travel package?
Yes, you're in control. We offer more than 550 partner airlines throughout the world, so you can tailor your Highland Park escape according to your travel preferences.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
