Highland Park Holidays from £876

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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
This was our second stay here. We were particularly impressed by the staff and customer service. It’s the kind we get in 5stars hotels overseas in the Middle East or SouthEast Asia. Impeccable. A special shout out to Pablo Criado for his warm and enthusiastic welcome and making sure that we had a great stay! I am now a fan and will only stay at Trump Chicago when in Chicago downtown.

Reviewed on 5 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.

Reviewed on 1 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Thank you LondonHouse!! Definitely top notch for my first visit to Chicago!

Reviewed on 5 Jul 2025

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

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 £164 per night from 26 Jul to 27 Jul
£164
26 Jul - 27 Jul
includes taxes & fees
8/10 Very Good! (2,049 reviews)
"Convenient to airport after flight got cancelled not once but twice ."

Reviewed on 2 Jul 2025

Hilton Chicago O'Hare Airport
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 £122 per night from 8 Jul to 9 Jul
£122
8 Jul - 9 Jul
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Great location and decent rooms. I had a strange experience in that two days in to my four day stay management ( dressed in plain, casual clothes of shorts and tshirt) came to my door and told me I wasn’t supposed to be in my room; that my room was supposed to be vacant. I would have questioned wether ..."

Reviewed on 2 Jul 2025

The Chicago Hotel Collection Ambassador Gold Coast
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 £134 per night from 5 Aug to 6 Aug
£134
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (1,701 reviews)
"I like it because I get to relax"

Reviewed on 4 Jul 2025

Hyatt Regency O'Hare Chicago
See all 2,498 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Highland Park

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Highland Park

Frequently asked questions

How much does a Highland Park travel package cost?
The most affordable Highland Park travel package is £876, 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.