Deals on vacations and trips to Highland Park

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Highland Park flight + hotel vacation packages

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Chicago Marriott Downtown Magnificent Mile
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
JW Marriott Chicago
Fairmont Chicago at Millennium Park Gold Experience
Level Chicago - River North

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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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Frequently asked questions

How much are vacation packages to Highland Park?
With vacation packages available for only $348, there’s no need to wipe out your bank balance for your getaway to Highland Park. Travelocity is here to help. Bundle your hotels, flights and experiences into a convenient package and land exciting discounts. The more you book, the greater the savings.
How long should my Highland Park vacation be?
Around 2 nights is the average amount of time visitors spend in Highland Park. But the perfect trip length all comes down to how many magical memories you want to make. Why not allow a few extra days and discover some hidden treasures?
Where can I get the best vacation package deals for Highland Park?
Travelocity is here to help you find a Highland Park package deal. With as many as 400 airlines and 1,000,000 properties across the world, there’s no doubt you’ll be able to put together the perfect itinerary.
Why should I purchase my Highland Park vacation bundle via Travelocity?
Because we believe in crafting one-of-a-kind vacation experiences. From hotels and flights to car rentals and activities, our packages make traveling a breeze. Our customer support is on hand 24/7 to make sure you’ll never wander alone. We also have an amazing Price Match Guarantee, so you can lock in your vacation knowing you’ve scored the best deal possible. If you find a lower price, we’ll match it!
Will I save money on my Highland Park car rental if I book it with a hotel or flight?
Certainly — combine your hotel, car and flight into a Highland Park vacation package and you’ll save a tidy sum. With so much to see and do in Highland Park, having your own wheels will make exploring a breeze. Once you’re in the driver’s seat, crank up the tunes and find your way to Milwaukee Art Museum, a famous sight approximately 60 mi from Highland Park.
What is the best time of year to go to Highland Park?
Going in the quietest months of the year, February, March and December, has its upsides — think more affordable hotels and flights and less bumping elbows with masses of tourists. But there’s a real appeal to the destination during the busiest season. More events will be on and more attractions will be open in May, June and July. If you’re on a budget, generally offers the lowest hotel prices. Expect to pay more for a room in .
Which airport is best for Highland Park?
O’Hare Intl. Airport (ORD) is one of the best airports for Highland Park. It’s situated 15 mi south of the city center. Other options available to you are General Mitchell Intl. Airport (MKE) (55 mi away from central Highland Park) and Midway Intl. Airport (MDW) (25 mi away from central Highland Park).
What is there to do in Highland Park?
While veering off the tourist trail is no doubt rewarding, you shouldn’t miss the big-name attractions that make a destination famous. Ravinia Pavilion and Ravinia Park are a couple of them in Highland Park.
Where should I stay when visiting Highland Park?
If you’re looking for somewhere to spend your nights, check out the Courtyard by Marriott Chicago Highland Park/Northbrook. It’s the top pick for many visitors.