Highland Park Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
- Rest easyPlan, book, and manage your trip all in one place
Your Highland Park Vacation
Planning your next big adventure is a piece of cake with a Highland Park vacation package. The neighborhood 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 vacation is just clicks away with Expedia.
Top Highland Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,265
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations.
Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay.
The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service.
This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨
Reviewed on Sep 18, 2026
Ready to book your vacation to Highland Park?
Highland Park Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $213
CA $253 total
Sep 30 - Oct 1
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
CA $260
CA $297 total
Oct 4 - Oct 5
includes taxes & fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
CA $251
CA $294 total
Oct 17 - Oct 18
includes taxes & fees
8.6/10 Excellent! (1,394 reviews)
"Everything was great!"
Reviewed on Sep 17, 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 is just one of the places to see in Highland Park, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Ravinia Pavilion
9.6/10 (7 reviews)
You can make plans for a show at Ravinia Pavilion during your stay in Highland Park. Wander around the area's picturesque gardens or experience its great live music.
What to do in Highland Park
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Frequently asked questions
How much does a Highland Park vacation package cost?
You can pick up a vacation package to this popular destination from CA $674 on Expedia. But how much your vacation to Highland Park costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Highland Park?
If you're looking to book a cheap Highland Park vacation package, consider planning a trip in December, January and February. You'll generally find better rates on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Highland Park?
With about 2 days, you'll have enough time to visit popular neighbourhoods such as Riverwoods and Bannockburn during your Highland Park vacation. Remember to also add Highland Park Country Club and Conway Farms Golf Club to your must-do list. Searching for more adventures? Consider exploring outside of Highland Park on day trips and tours.
Is it worth booking a vacation package to Highland Park?
Whether you want to visit top sights such as Chicago Botanic Garden and Ravinia Pavilion on your Highland Park vacation, or coming for its excellent shopping, golfing and dining, there's something for everyone here. With so much to experience, you'll soon discover why so many people think Highland Park is a good vacation destination.
How to find the best Highland Park package deals?
Start your search for a Highland Park package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Highland Park package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Highland Park escape underway.
Is it cheaper to book a Highland Park vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Highland Park vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Highland Park?
If you're considering a spontaneous Highland Park vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Highland Park?
- Choose your travel dates: The things you'd like to do in Highland Park and your favourite season can help you decide when to travel.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Highland Park.
- Decide your trip length: Think about how much time you want to spend exploring Highland Park. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the perfect Highland Park vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
