
Highwood Vacation Packages
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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.
Top Highwood Vacation Deals

Level Chicago Fulton Market
Reviewed on Feb 9, 2026

La Banque Hotel
Reviewed on Jan 26, 2026


Aloft Chicago Downtown River North
Reviewed on Feb 8, 2026

The Emily Hotel
Reviewed on Feb 10, 2026
Highwood Hotel Deals

Hilton Chicago O'Hare Airport
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV
Reviewed on Feb 9, 2026

Marriott Chicago O'Hare
Clean room and staff was excellent
Reviewed on Feb 12, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
The friendliness of the staff.
Reviewed on Feb 9, 2026
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











