Highland Park Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
Jul. 19 - Jul. 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
One of the best hotels Ive ever been to and such a clean and beautiful city

Reviewed on Jun. 17, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 24 - Aug. 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
Good stay at the W, staff was very nice and organized. Would stay there again for sure.

Reviewed on Jun. 17, 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 19 - Aug. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
Amazing property in terms of location and amenities

Reviewed on Jun. 17, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 19 - Aug. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon

Reviewed on Jun. 17, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 24 - Aug. 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (983 reviews)
I would just improve the attention in the breakfast restaurant due to a bad experience. The rest was excellent

Reviewed on Jun. 2, 2024

Highland Park Hotel Deals

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 $218 per night from Jul. 2 to Jul. 3
CA $218
CA $256 total
includes taxes & fees
Jul 2 - Jul 3
8/10 Very Good! (1,008 reviews)
"Rooms were small and we had an issue with the deadbolt to start off. They fixed it quickly. But pull was run down and an probably use a update"

Reviewed on Jun. 16, 2024

Marriott Chicago O'Hare
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
Fully refundable
The price is CA $191 per night from Jul. 1 to Jul. 2
CA $191
CA $248 total
includes taxes & fees
Jul 1 - Jul 2
9/10 Wonderful! (1,005 reviews)
"The room had a dinky little espresso machine but no coffee. Ordering coffee to the room was insanely expensive. $5 just for ordering cream with the coffee. Really disappointing how they gouge you for coffee. Everything else was fantastic."

Reviewed on Jun. 16, 2024

Thompson Chicago, by Hyatt
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is CA $259 per night from Jul. 2 to Jul. 3
CA $259
CA $295 total
includes taxes & fees
Jul 2 - Jul 3
9.2/10 Wonderful! (1,593 reviews)
"Shuttle bus to airport is very convenient"

Reviewed on Jun. 18, 2024

Loews Chicago O'Hare Hotel
See all 2,331 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

Family Vacations

Frequently asked questions

How much does a Highland Park vacation package cost?
From just CA $838, you can custom build your Highland Park vacation package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Highland Park?
Secure flights that fit your schedule, add a hotel room to your booking and watch the savings grow with a Highland Park vacation package. It’s that easy! From flights and hotels to rental cars and activities, Expedia is where your cheap vacation begins. And with over 550 airlines and 1,000,000 properties across the globe to select from, you’ll never be short of choice.
Where should I stay in Highland Park?
You’ll want to stay where the action is. Many visitors like to book hotels around popular sights, like Chicago Botanic Garden, Ravinia Pavilion and Ravinia Park.
What are the top hotels in Highland Park?
Whether you’re planning to stay for just one night or a week in Highland Park, you’ll get a great night’s sleep at Courtyard by Marriott Chicago Highland Park/Northbrook. This option is popular with many travelers.
How far in advance should I book my Highland Park vacation?
Smart travelers will likely want to reserve their seats as early as possible. You can generally start comparing international airfares on Expedia up to 12 months before your flight. If you’ve left booking to the last minute, fear not. Discounted prices sometimes occur just weeks before departure dates.
What does an Expedia Highland Park travel package include?
Select from any combination of rental cars, flights and hotels. Once you’ve made your booking, you can add activities and experiences. Want to pick your fare class? That’s also easy to do. The choice is yours when it comes to organizing your ideal Highland Park getaway.
What should I know before booking a Highland Park travel package?
You’ll score excellent savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything together just makes things easier. So why waste your time or money? Whether you’re putting together an upscale romantic escape or a low-cost family break, browse our package deals today.
Can I choose my airline with a Highland Park Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Simply choose the airline you want and create the perfect Highland Park escape.
If I'm not able to travel, can I cancel my Highland Park vacation package?
If your travel plans in Highland Park have been upended, it’s good to know that you can amend or cancel your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may impose fees. For more details, check our Customer Service Portal.

Discover the most popular places to visit in Highland Park

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Highland Park

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $255
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $121
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Highland Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.