Highwood enjoys the good life with a thriving dining scene, festivals, and nightlife that attracts visitors from across the North Shore.

The city is known for its award-winning restaurants, offering everything from Italian to French cuisine. In the summertime, residents enjoy Highwood’s popular Evening Markets, recognized among the best on the North Shore with numerous vendors and a variety of musical acts.

Additional community events include the annual Holiday Lighting Ceremony and Highwood Days, the city’s oldest festival. The city is also home to one of the area’s premier bocce facilities, Highwood Bocce Club.

Aptly named for its high elevation relative to Lake Michigan and its wooded setting, Highwood is located just north of Highland Park. Real estate varies from duplexes and ranches to luxury apartments, condominiums, and single-family homes. The community also includes part of Fort Sheridan, a master-planned residential community and national historic landmark that was originally a U.S. military base.  

The main highway to Highwood is US-41, which connects Chicago to Milwaukee. Commuter rail service includes two Metra train stations offering direct access to downtown Chicago.

Nearby Public Transportation

Union Pacific North

at Highwood Metra, Fort Sheridan Metra

School Districts

Twp Hsd 113

North Shore Sd 112

Elementary Schools

Middle Schools

School information is provided by the National Center for Education Statistics. This information should only be used as a reference and does not warrant or guarantee enrollment. Please contact applicable schools or school districts directly to verify information and enrollment eligibility.

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Average Sales Price


Average Days on Market


Sales Prices vs. List Price


Data represents the average over the past 12 months. All information deemed reliable, but not guaranteed.