Time Out says
Stretching from Hollywood Avenue on the north to 71st Street to the south, the 18-mile-long Lakefront Trail is a great way to experience the Chicago lakefront. It also serves as a reminder for residents of why our city, edged by sparkling blue water, is a pretty nice place to live. Whether you walk, run, blade or bike, be alert and cautious: Some cyclists fly down the path by as if competing in the Tour de France, while other pedestrians saunter along, oblivious to the flow of traffic. There are a number of beaches accessible along the trail. Especially worth visiting is the scenic, less-crowded south-shore portion.