Streeterville may be most known as the gateway to Navy Pier, but the story of its namesake “Captain” George Wellington Streeter is a controversial one woven with accounts of false property deeds, open gun battles and years of eviction suits. It began in 1886 when Streeter’s ship was lodged in a sandbar after a storm, after which he invited building contractors to continue piling waste around it — a practice that had begun when Lake Michigan was used as a dump during the cleanup that followed the Great Chicago Fire of 1871. He claimed this newly created marshland as his own and it wasn’t until decades later that the courts could finally rule against him.
You’ll find a statue of “Cap” standing on this formerly contested site as a reference to its early history, but even more colorful than this eccentric character is the neighborhood’s main attraction: Navy Pier. A playland filled with amusement rides, gift shops, and eateries, its docks are lined with sightseeing boats and bicycles. In addition to sweeping lakefront views, Navy Pier is home to its own beer garden and evening fireworks in the summer, as well as year-round favorites, Chicago Children’s Museum and Chicago Shakespeare Theater.
Beyond the Pier, there’s much to do in Streeterville. The neighborhood boasts a range of dining options, from four-star French cuisine to pub fare. Entertainment can be had in the form of outdoor recreation at Ohio Street Beach or art appreciation at the Museum of Contemporary Art.