
Highwood Vacations from $238
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Your Highwood Vacation
Book a custom vacation package to Highwood and get ready to experience this incredible city how you like. Consider staying in the neighborhood of Riverwoods, which is good for nature and tons more. A trip to Highwood is an excellent opportunity to take in the sights. Be sure to look around renowned attractions like Chicago Botanic Garden, Lake Forest College and Marriott Theatre. No matter your travel plans or the size of your budget, putting together a tailored Highwood vacation is a breeze with Expedia.
The Latest Highwood vacation packages

Hilton Grand Vacations Club Chicago Magnificent Mile
Reviewed on Oct 4, 2025

Hotel Riu Plaza Chicago
Reviewed on Oct 8, 2025

Pendry Chicago
Reviewed on Oct 7, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 6, 2025

Park Hyatt Chicago
Reviewed on Oct 2, 2025
Discover the most popular places to visit in Highwood

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

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood

Skydeck - Willis Tower Admission

Chicago: Navy Pier Centennial Wheel Ticket
Highwood Hotel Deals

Hyatt Regency O'Hare Chicago
Reviewed on Oct 7, 2025

Marriott Chicago O'Hare
Reviewed on Oct 3, 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Reviewed on Oct 4, 2025
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 |
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