Absolutely stunning and offers fantastic walk areas in visibility of Chicago skyline Chicago’s Lakefront Trails welcome residents and visitors from around the City. On any given day activity along the pedestrian and bike trails includes people commuting to work, training for marathons, caregivers with children in strollers, tourists on rental bikes, and people taking a leisurely stroll. Chicago’s scenic Lakefront Trail is an 18-mile paved path that follows the Lake Michigan shoreline on the city’s eastern edge.