Highland Park Vacations from $388

Book a Hotel + Flight or Car together to unlock savings

Photo by Meghan hernandez
Choose one or more items to build your trip:

Your Highland Park Vacation

Save time and energy on your travel planning with a Highland Park vacation package. One of the best neighborhoods to stay in this captivating city is Riverwoods, which is good for nature and a lot more. If sightseeing is part of the plan during your trip to Highland Park, check out major attractions like Chicago Botanic Garden, Ravinia Pavilion and Lake Forest College. Whoever you're going away with and whether your budget is big or small, your dream Highland Park vacation is just clicks away with Expedia.

The Latest Highland Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 31 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
Well kept, great location and friendly staff!

Reviewed on May 31, 2024

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,432 reviews)
Perfect. The minus points I found out were a little bit far from the metro station and water in the pool is not good enough.

Reviewed on May 31, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Very nice staff except for the guy at the front desk with the hair braided back very rude. I pray I never encounter him again I come to the Trump all the time and this was my first encounter with him very unwelcoming and dry.

Reviewed on Jun 4, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Highland Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
29,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Marriott Theatre, North Shore Center for the Performing Arts and Kohl Childrens Museum

Highland Park Hotel Deals

Claridge House
Claridge House
4 out of 5
1244 N Dearborn Parkway, Chicago, IL
The price is $124 per night from Jul 1 to Jul 2
$124
$175 total
includes taxes & fees
Jul 1 - Jul 2
8.2/10 Very Good! (1,114 reviews)
"Great hotel!"

Reviewed on May 31, 2024

Claridge House
Best Western At O'Hare
Best Western At O'Hare
2.5 out of 5
10300 W Higgins Road, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is $110 per night from Jun 30 to Jul 1
$110
$125 total
includes taxes & fees
Jun 30 - Jul 1
7.2/10 Good! (1,880 reviews)
"Dirty carpet. Dead bedbug found."

Reviewed on Jun 5, 2024

Best Western At O'Hare
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 $159 per night from Jul 1 to Jul 2
$159
$187 total
includes taxes & fees
Jul 1 - Jul 2
8.2/10 Very Good! (1,011 reviews)
"My children, and I stayed here recently, and this hotel is absolutely gorgeous!! & was very clean! The shrimp from their restaurant was delicious along with the quesadillas!"

Reviewed on Jun 2, 2024

Marriott Chicago O'Hare
See all 2,348 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Highland Park vacation package cost?
From just $388, 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(2,128 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(347 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 McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Highland Park

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
94% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Highland Park

Other vacations you might like

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