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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,049, price is now CA $760 per person
CA $760
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Very nice rooms. Smaller casino but nice. No late night food options.

Reviewed on Jul 9, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,834, price is now CA $1,264 per person
CA $1,264
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Room was clean and large, staff were helpful and polite. Would definitely stay again!

Reviewed on Jul 10, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.

Reviewed on Jul 9, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 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 $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,727 reviews)
"Great place in a great location. Restaurant and breakfast buffet were excellent."

Reviewed on Jul 10, 2026

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 $324 per night from Aug 9 to Aug 10
CA $324
CA $381 total
Aug 9 - Aug 10
includes taxes & fees
Hilton Chicago O'Hare Airport
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 CA $239 per night from Aug 3 to Aug 4
CA $239
CA $273 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,810 reviews)
"Amazing Location"

Reviewed on Jul 9, 2026

Hyatt Regency O'Hare Chicago
See all 2,573 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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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 $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and 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 $760 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.