Slot Machines for Bars in Wicker Park, Chicago

History

Charles and Joel Wicker, wholesale grocers who settled in Chicago in 1839, laid out a subdivision here and in 1870 gave the City a four-acre triangle for a public park. The City fenced it against cows and dug a small lake, and the blocks around it filled with middle- and upper-class homes.

The houses went up in the decades after the Great Chicago Fire. Germans and Scandinavians built first, and brewery owners put up Victorian mansions on Hoyne Avenue, which earned the name Beer Baron Row. Poles followed in such numbers that the district was called the Polish Gold Coast, and the blocks around the Polish Triangle, where Division meets Milwaukee and Ashland, held hundreds of Polish-American businesses.

By 1970 Latinos were 39 percent of residents and the neighborhood held the city's second largest Puerto Rican concentration. The Flat Iron Building at Milwaukee and North filled with artists' studios, artists settled in through the 1980s, and by the 1990s the six corners drew galleries, shops and music clubs. Rising rents later pushed most of them out. The district's houses, built from 1870 to 1930, became a Chicago Landmark district in 1991.

The area today

The park is still the center, a triangle on Damen Avenue with a fieldhouse the Park District rebuilt in 1985. Just north, Milwaukee, North and Damen cross at the six corners under the Damen Blue Line station, built in 1895, rehabilitated in 2014, and called by Ald. Joe Moreno a vital link to the Wicker Park and Bucktown neighborhoods. The Flat Iron Arts Building holds that corner, studios upstairs and bars at street level. The old rail embankment on Bloomingdale Avenue is now the 606 trail, shared with Bucktown and Humboldt Park. Milwaukee runs southeast to the Polish Triangle at Division and Ashland, where a few Polish businesses hold on. In 2025 the alderman and the Wicker Park Bucktown Chamber of Commerce began closing Milwaukee from the six corners to Ashland to traffic on Sunday afternoons so people could shop, eat and drink in the street.

Bars and restaurants here

If your room is on Milwaukee between the six corners and Division, you know the pattern: a weeknight crowd off the Blue Line and down from the apartments over the storefronts, then weekend nights when the strip fills from both ends and people drift from a cocktail bar to a music room to a late kitchen. North Avenue takes the spillover east and west from the corner, Damen runs quieter rooms up toward Bucktown, and Division Street has its own stretch of restaurants and patios west from the Polish Triangle. The rooms are old storefronts with back patios and walk-ups above, and the owners who last are the ones the regulars know by name.