JR Five Hundred Pixels

Like NYC's High Line, Chicago's 606 is a similar urban-cool elevated path along an old train track. Bike or stroll past factories, smokestacks, clattering L trains and locals' backyard affairs for 2.7 miles between Wicker Park and Logan Square. It's a fascinating trek through Chicago's socioeconomic strata: moneyed at the east, becoming more industrial and immigrant to the west.

The trail parallels Bloomingdale Ave (the border between Wicker Park and Bucktown), with access points every quarter mile. The entrance at Churchill Field (1825 N Damen Ave) is a handy, sculpture-laden place to ascend. For those wanting to cycle, there's a Divvy bike-share station a few blocks from the trail's eastern end at the corner of N Marshfield Ave and W Cortland St.