Highland Park Vacation Packages

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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,117, price is now CA $818 per person
CA $818
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,160, price is now CA $2,208 per person
CA $2,208
per person
Dec 28 - Jan 2
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,958, price is now CA $1,430 per person
CA $1,430
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Love it here!!! Been twice this year.

Reviewed on Nov 14, 2026

Ready to book your vacation to Highland Park?

 

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Highland Park Hotel Deals

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 CA $165 per night from Dec 6 to Dec 7
CA $165
CA $197 total
Dec 6 - Dec 7
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
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 CA $261 per night from Dec 12 to Dec 13
CA $261
CA $306 total
Dec 12 - Dec 13
includes taxes & fees
8.6/10 Excellent! (2,599 reviews)
"El acceso al aeropuerto resulta muy conveniente."

Reviewed on Nov 13, 2026

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Nov 28 to Nov 29
CA $204
CA $240 total
Nov 28 - Nov 29
includes taxes & fees
Marriott Chicago O'Hare
See all 2,654 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.
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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.
See properties

What to do in Highland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Highland Park

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 $818 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.