Originally part of the Edgewater neighborhood, the area now known as Uptown was developed as a summer playground for members of Chicago's elite class in the late 19th century, due in large part to its close proximity to Lake Michigan. But the area's desirable location soon began to attract permanent residents in addition to those looking for a warm weather getaway. In the early 1900s, all of the city's northbound trains traveling from downtown ended in the Uptown area, and the neighborhood became a popular entertainment destination.

Uptown history includes a huge nod to film as the neighborhood was also the country's movie capital at one point. Between 1907 and 1918, Essany Studios (the historic building is still located on Argyle Street) made more than 2,000 silent movies. Charlie Chaplin, Gloria Swanson, Wallace Beery and Francis X. Bushman were frequent visitors at the studio. By 1918, though, the movie industry moved west, driven away by the often-wintry Chicago weather to the sunny climate of Los Angeles.

Still, in the 1920s, Uptown was the city's fastest growing area. The neighborhood became independent of Edgewater due to a construction and economic boom, and was promoted as Chicago's version of New York City's Manhattan island—packed with glitz, glamour and excitement. Even the street at Uptown's commercial center was crowned 'Broadway.'

Large apartments and hotels were erected to accommodate the growing influx of single adults. Often new to the city, they met up at the neighborhood's many bars, restaurants, dance halls and theaters. In fact, Uptown soon became the north side's leading retail and entertainment district with places like The Rainbo, a popular outdoor music garden, the Arcadia Ballroom and the 5100 Club, a hip comedy nightclub.

The entertainment district's popularity waned throughout the second half of 20th century, but over the past few years it has been experiencing a revival. New restaurants, bars and shops are opening every year, tucked in among the district's historic surviving members like the Aragon Ballroom and the Green Mill Lounge, which is famous for being a favorite spot of Al Capone.

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