Highland Park & Highwood

Highland Park and Highwood are the North Shore’s most lived-in pair: Highland Park has Ravinia Festival, the Chicago Symphony’s outdoor summer home, a real downtown on Central Avenue and a long lakefront with ravines and beaches, while Highwood, squeezed between it and the old Fort Sheridan, packs more restaurants per block than any town on the shore, a legacy of its Italian immigrant families and the soldiers they fed. Highland Park is affluent and residential; Highwood is small, dense and working-class by North Shore standards. Fort Sheridan’s officers’ quarters are now houses.

Where it is

On the map, Highland Park runs from Glencoe north to Lake Forest between the lake and the Skokie River, with Highwood a small wedge inside it along Sheridan Road and Green Bay Road north of downtown. Metra’s Union Pacific North line stops at Ravinia Park (concert days), Ravinia, Highland Park, Highwood and Fort Sheridan, about 50 minutes to Ogilvie. Sheridan Road and Green Bay Road run north-south, and Route 41 and the Edens Spur connect to the expressways west. Driving to the Loop takes 45 minutes to an hour.

What to know if you’re moving here

Highland Park is Lake County, which matters for taxes, and Highwood is its own small world.

• Housing is single-family homes and condos in Highland Park and small houses and apartments in Highwood, built from the 1900s on, with typical prices of roughly $400,000 to $3 million as a broad editorial estimate as of September 2026.
• Parking is driveways in Highland Park and a mix of street and municipal lots in Highwood’s downtown.
• Public schools are North Shore School District 112 for both towns and Township High School District 113 (Highland Park High School).
• Both towns are in Lake County, where property tax rates and assessment practices differ from Cook County next door.
• Ravinia season, June through September, brings concert traffic to the south end of Highland Park several nights a week.
• The drawback is a long commute: 50 minutes on Metra and often more by car.

What to do if you’re visiting

Ravinia in summer and Highwood’s restaurant strip year-round are the reasons to come, and the Metra stops serve both.

• Ravinia Festival on Green Bay Road runs June through September, with lawn tickets and a Metra stop that opens only on concert days.
• Highwood’s oldest table is at The Del Rio Restaurant on Green Bay Road, where the Pigati family has served Bolognese-style Italian dinners since 1923, while a few blocks over the double-decker pizza at Buffo’s Restaurant on Sheridan Road has drawn crowds since 1977.
• Beer and tacos at Steep Ravine Brewing Company, the Roger Williams Avenue brewery formerly called Ravinia Brewing, are a short walk from the Ravinia Metra stop.
• Rosewood Beach in Highland Park has a modern beach house and a ravine walk down from Sheridan Road.
• Downtown Highland Park along Central Avenue has a 1977 hot dog stand turned grill, Michael’s Grill & Salad Bar, and a bookstore in a two-story house, Matchmaker Bookshop, both on Second Street.
• Galleries with free admission and a fall Recycled Art Sale make The Art Center Highland Park on Sheridan Road the stop for art, and Fort Sheridan’s parade ground and lakefront trail, now a forest preserve, are open for walking.