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

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 7 - Jun. 10
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on Apr. 14, 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
Jun. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 1 - Jul. 6
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on Apr. 15, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Every single person working at this facility was extremely polite and welcoming. I’ve stayed in so many hotels across the world and I have to say this was the best experience I’ve ever had staying at a hotel. Ordered food at 3am and it was fantastic. My cloths got folded in the short period of time my wife and I left the room and came back to a spotless room. Overall amazing experience. Will be staying here every time I come to Chicago.

Reviewed on Apr. 16, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 5 - Jul. 8
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
YOGA AND POOL AND ELEGANT LUNCH AREA PLUS LOVE MY SUITE !!!!

Reviewed on Apr. 17, 2024

Prices and availability subject to change. Additional terms may apply.

Highland Park Hotel Deals

Ambassador Chicago, part of JdV by Hyatt
Ambassador Chicago, part of JdV by Hyatt
4 out of 5
1301 N State Pkwy, Chicago, IL
Fully refundable
The price is CA $186 per night from Apr. 23 to Apr. 24
CA $186
CA $246 total
includes taxes & fees
Apr 23 - Apr 24
8.6/10 Excellent! (1,004 reviews)
"Every staff member went above and beyond"

Reviewed on Apr. 18, 2024

Ambassador Chicago, part of JdV by Hyatt
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 $253 per night from May 10 to May 11
CA $253
CA $297 total
includes taxes & fees
May 10 - May 11
7.6/10 Good! (1,925 reviews)
"Easy access. Great service."

Reviewed on Apr. 17, 2024

Hilton Chicago O'Hare Airport
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 CA $107 per night from Apr. 25 to Apr. 26
CA $107
CA $122 total
includes taxes & fees
Apr 25 - Apr 26
7.2/10 Good! (1,688 reviews)
"The staff is awesome"

Reviewed on Apr. 16, 2024

Best Western At O'Hare
See all 2,352 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.

Explore other types of vacation packages

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 $708, 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 McCormick Place

McCormick Place

4.5/5(141 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
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 Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
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.