Highwood Vacations from $501

Book a Hotel + Flight or Car together to unlock savings

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Your Highwood Vacation

Book a custom vacation package to Highwood and get ready to experience this interesting city on your own terms. Think about spending some time in the neighborhood of Riverwoods, which is good for nature and more. If your trip to Highwood includes a little sightseeing, hit up popular attractions like Chicago Botanic Garden, Ravinia Pavilion and Lake Forest College. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Highwood vacation plans into motion!

The Latest Highwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 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
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (2,193 reviews)
Everyone was very helpful and nice, rooms were clean.

Reviewed on May 15, 2024

Highwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
5,400
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Genesee Theater, Marriott Theatre and North Shore Center for the Performing Arts

Highwood Hotel Deals

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 May 21 to May 22
$110
$125 total
includes taxes & fees
May 21 - May 22
7.2/10 Good! (1,797 reviews)
"Close to Airport"

Reviewed on May 14, 2024

Best Western At O'Hare
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
3 out of 5
6810 Mannheim Rd, Rosemont, IL
Fully refundable
The price is $131 per night from Jun 9 to Jun 10
$131
$154 total
includes taxes & fees
Jun 9 - Jun 10
8.2/10 Very Good! (2,274 reviews)
"Great atay"

Reviewed on May 13, 2024

Hyatt Place Chicago/O'Hare Airport
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 $169 per night from May 23 to May 24
$169
$198 total
includes taxes & fees
May 23 - May 24
8.2/10 Very Good! (1,001 reviews)
"The staff were so helpful and friendly, makes me want to come back. Great customer service."

Reviewed on May 13, 2024

Marriott Chicago O'Hare
See all 1,229 properties in Highwood
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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Highwood vacation package cost?
The most affordable Highwood package is $501, so your dream escape can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to customize a package that matches your travel style.
How do I get a cheap travel package to Highwood?
Crafting your own Highwood vacation package with Expedia is an easy way to save. We offer more than 550 airlines and 1,000,000 properties all over the world. With such an awesome range to choose from, you’ll have no hassles putting together your ideal adventure.
Where should I stay in Highwood?
With loads to discover in Highwood, it’d be handy for you to book a hotel close to its attractions. Lake Forest College, Highland Park Country Club and Highland Park Ambulatory Care Center are some interesting ones to add to your must-see list.
How far in advance should I book my Highwood vacation?
It’s always wise to book early. Airlines usually advertise flight tickets up to a year prior to departure, and this is a fantastic opportunity to score some of the lowest prices. Boss just told you to use up your vacation time in a few weeks? Don’t fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Highwood travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Highwood package that’s perfect for you. Vacationing for a while? Give some thought to a hotel, flight and rental car bundle. If you can only squeeze in a quick getaway, a flight and hotel deal may suit you better. Experiences can also be added after you’ve booked. Our travel packages make it a breeze to save and plan.
What should I know before booking a Highwood travel package?
You can save big by bundling your airfares, hotels and rental cars. Once you’ve made your booking, you can add on sightseeing tours or experiences. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Highwood Expedia vacation package?
Yes, you can. Expedia has access to more than 550 airline partners across the globe, so choose the carrier that best suits your travel preferences.
If I'm not able to travel, can I cancel my Highwood vacation package?
If your vacation plans in Highwood have changed, it’s comforting to know that you can cancel or amend your booking. If you booked within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. For more information, visit our Customer Service Portal.

Discover the most popular places to visit in Highwood

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 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
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

What to do in Highwood

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$229
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
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Highwood

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