On any given day, you can find a spot that will stun you with its beauty, connect you to the past, and remind you that you’re part of something larger and more complicated than any individual. These are my top four:
18th Street Bridge: Refurbished in 2015, the bridge spanning the South Branch of the Chicago River perches you atop Ping Tom Memorial Park, named for the lifelong Chinatown resident who spearheaded its creation in a neighborhood that lacked its own green space. Stand on the bridge looking north at dusk and you’ll be treated to the city’s lights flickering onto a winding river, historic bridges, and warehouses giving way to skyscrapers — a nod to the city’s long and varied contributions to industry.
Cricket Hill: A 45-foot mound may not be much in the grand scheme of hills, but on the North Side of Chicago (at 4500 N. DuSable Lake Shore Dr.) it’s enough to give you a bird’s-eye view of the lake to the east, Uptown to the west, and a collection of joggers, bikers, soccer players, and gleeful children careening wildly in all directions. Built in the ’40s with displaced dirt from nearby construction, it’s a monument to ingenuity.
The 606: Any spot on this 2.7-mile trail along a former rail line connecting Humboldt Park, Logan Square, Wicker Park, and Bucktown offers a glimpse into Chicago’s intricate, interlocking neighborhoods, its devotion to preserving green spaces, its sweeping landscapes, and its humanity. Don’t miss Graffiti Garden, on the south-facing walls between Kimball and Central Park Avenues. The 606 runs along the Bloomingdale Trail (1800 north) between Ashland and Ridgeway Avenues.
Promontory Point: Designed by landscape architect Alfred Caldwell, this chunk of land (5491 S. DuSable Lake Shore Dr.) within the 600 acres of Burnham Park juts east enough into Lake Michigan to offer sweeping southern views of the skyline. It’s a burst of colors in the fall. Quiet and serene in the winter. Teeming with life in the spring. Welcome lake access in the summer. Year-round, a perfect spot to watch a sunrise.