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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


Level Chicago – Old Town
Reviewed on Nov 25, 2025

Level Chicago Fulton Market
Reviewed on Nov 25, 2025


Pendry Chicago
Reviewed on Nov 26, 2025
Discover the most popular places to visit in Highwood

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.

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

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 Bulls Basketball Game at United Center

Wendella's 90-min Chicago River Architecture Tour
Highwood Hotel Deals

Hilton Chicago O'Hare Airport
Nice stay staff is very accommodating and friendly.
Reviewed on Nov 27, 2025

Hyatt Regency O'Hare Chicago
The room was clean and comfortable. Breakfast was amazing!
Reviewed on Nov 24, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
The room was nice, the staff was pleasant, attentive, and helpful. As a handicapped person the hotel has plenty of ramps.
Reviewed on Nov 26, 2025
Find the Best Highwood Vacation Packages
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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