The 606 / Bloomingdale Trail

The 606 is a 2.7-mile elevated rail-trail built on a former industrial railroad line through four of Chicago's trendiest neighbourhoods — Wicker Park, Bucktown, Humboldt Park, and Logan Square. Named after Chicago's zip code prefix, the trail opened in 2015 and has become one of the most popular running, cycling, and people-watching routes in the city, a Midwest High Line that puts you 17 feet above street level with unobstructed views of the neighbourhood below.

The trail follows the former Bloomingdale Line, a freight railroad that was elevated in 1913 and abandoned in 2001. The conversion preserved the industrial character — concrete pillars, steel bridges, occasional stretches of original rail — while adding native plantings, lighting, public art installations, and access ramps at regular intervals. Running or cycling the full length takes you from the boutiques of Wicker Park through increasingly residential blocks to the wide boulevards and Puerto Rican heritage of Humboldt Park.

The neighbourhoods along the trail are some of Chicago's most dynamic — Wicker Park for vintage shopping and cocktail bars, Bucktown for restaurants and galleries, Logan Square for the craft beer and independent music scene. The trail connects them all in a linear park that feels like a neighbourhood rather than a tourist attraction. Come at sunset for the best light and the most runners.