America's Best Urban Running Trails

Lakefront Trail, Chicago

Chicago is a city with an awesome and towering skyline—and this 18.5-mile path along the shore of Lake Michigan gives you ample opportunities to appreciate it. Start at the Navy Pier, then turn south along the paved lakeside trail. You’ll pass Buckingham Fountain, the Shedd Aquarium and Soldier Field, home to the Chicago Bears. When you turn around for the return trip, you’ll be treated to a fabulous view of the city’s skyscrapers, including the Aon Center, the John Hancock Center and the Willis Tower (currently the tallest building in the United States). The trail north of the Navy Pier will lead you to Oak Street Beach, a good place to rest after your run.