Highwood, IL Area Guide

Highwood's story is rooted in its position on the highest ground between Chicago and Milwaukee, a distinction that gave the city its name when early settler Thomas Curley proposed "High Woods" to describe the tree-covered ridge. The arrival of the Chicago North Shore and Milwaukee Railroad in 1851 put Highwood on the map as a regional transit hub, a role the community still plays today through the Metra Union Pacific North Line station just steps from downtown. The former Fort Sheridan military base, decommissioned in 1993, now lives on as a National Historic Landmark district just north of the city, where preserved brick buildings and open grounds have been adapted into residences and forest preserve land.

Highwood has earned a reputation as one of the most restaurant-dense communities on the North Shore. Green Bay Road and Waukegan Avenue form the heart of this culinary scene, lined with casual eateries and neighborhood bars that draw both locals and visitors. Mexican cuisine is equally prominent, with spots serving everything from tacos to the area's beloved Mexican-style hot dogs. Happy hour regulars and weekend diners alike enjoy a relaxed, convivial atmosphere that feels more like a city neighborhood than a small suburb.

Highwood's own Metra station on the Union Pacific North Line puts downtown Chicago within easy reach, with trains running south to Ogilvie Transportation Center and north to Kenosha, Wisconsin. The Fort Sheridan station is just over a mile away, adding a second nearby option. For drivers, Sheridan Road and Green Bay Road handle most local traffic, while Interstate 94 is accessible to the west and US Route 41 runs nearby for regional travel. Chicago O'Hare is roughly 34 minutes by car. At just one square mile, the city is compact enough that many daily errands are walkable, and Pace suburban bus service connects residents to neighboring North Shore communities. Rideshare options are readily available throughout the area.

Highwood sits between two natural anchors that give residents easy access to the outdoors despite the city's compact footprint. The Fort Sheridan Forest Preserve, just a five-minute drive north, offers wooded trails, natural areas, and views of the historic military architecture that once defined the site. To the east, the Openlands Lakeshore Preserve is less than a mile away and provides direct access to Lake Michigan, where visitors can hike, swim, and enjoy beachside picnics. Prairie Wolf Slough and Heller Nature Center are both within a ten-minute drive, offering wetland scenery and nature education programs for those who enjoy exploring local ecosystems.

Highwood offers a more accessible entry point to North Shore living compared to its immediate neighbors. Average rent for a one-bedroom apartment is $1,992 per month, with studios averaging $1,886 and two-bedrooms at $2,391. Those figures sit above the Illinois statewide average, reflecting the area's North Shore location, but fall notably below nearby Highland Park, Lake Forest, and Deerfield. Rents have remained relatively stable year over year, with modest movement across unit sizes.

Highwood's compact commercial core along Green Bay Road and Waukegan Avenue brings together a mix of independent retailers, local businesses, and everyday conveniences within easy walking distance for most residents. The city's small-town scale makes browsing feel relaxed and personal rather than sprawling. Shopping clusters along Washington Avenue and stretches of Sheridan Road round out the local retail scene with additional small storefronts and service-oriented shops. Residents looking for larger retail destinations, department stores, or big-box options have convenient access to nearby Highland Park and Lake Forest, and Westfield Hawthorn in Vernon Hills is within a short drive for a full mall experience.

Highwood delivers an outsized dining and nightlife scene from just one square mile on Chicago's North Shore, with Italian-American and Mexican restaurants lining Green Bay Road and a Metra station offering a direct rail link to downtown Chicago. Bookended by the Fort Sheridan Forest Preserve and close to Lake Michigan, the city also stands out as the most affordable rental option among its North Shore neighbors.