A pebbly beach with waves at sunset.

Highland Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Highland Park vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Sept 23 - Sept 26

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very good (2,855 reviews)
    "Good experience in the middle of downtown."
    Reviewed July 20, 2026
    Roundtrip Toronto (YTO) - Chicago (ORD)
    YTZ - MDWNonstop MDW - YTZNonstop
    CA $1,241
    CA $831
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Aug 26 - Aug 31

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (533 reviews)
    Roundtrip Toronto (YTO) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YYZNonstop
    CA $2,214
    CA $1,485
    per traveller
    found 2 days ago
    Level Chicago Fulton Market
  • Sept 23 - Sept 26

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (4,761 reviews)
    Roundtrip Toronto (YTO) - Chicago (ORD)
    YTZ - MDWNonstop MDW - YTZNonstop
    CA $1,525
    CA $1,029
    per traveller
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Sept 23 - Sept 26

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,606 reviews)
    Roundtrip Toronto (YTO) - Chicago (ORD)
    YTZ - MDWNonstop MDW - YTZNonstop
    CA $2,040
    CA $1,404
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Sept 4 - Sept 7

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (504 reviews)
    "Good"
    Reviewed July 20, 2026
    Roundtrip Toronto (YTO) - Chicago (ORD)
    YYZ - ORDNonstop ORD - YTZNonstop
    CA $1,747
    CA $1,228
    per traveller
    found 1 day ago
    Level Chicago – Old Town

What to do in Highland Park

Highland Park Hotel Deals

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.

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 $831 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.