Slot Machines for Bars in Woodlawn, Chicago

History

Dutch farmers were Woodlawn's first residents in the 1850s, and the Illinois Central opened a station at Junction Avenue, now 63rd Street, in 1862. Chicago annexed the area in 1889. Jackson Park's selection for the 1893 World's Columbian Exposition brought 20,000 new residents and entrepreneurs, and developers pushed the elevated east along 63rd Street and put up large apartments and tourist hotels. Irish ironworker John Daley opened a lunch room on East 63rd in 1892, and by the 1920s the blocks around the Cottage Grove el stop held theaters, dance halls and cabarets, the Tivoli and the Trianon Ballroom among them.

In 1959 churches, block clubs and business owners invited Saul Alinsky's organizers in, which led to The Woodlawn Organization. The population peaked at 81,279 in 1960, when 89 percent of residents were African American, and fell to 27,086 by 2000. In the early 1990s community leaders began courting private developers, new businesses and a bank.

The area today

The Obama Presidential Center opened to the public in June 2026 at 6001 S. Stony Island Avenue in Jackson Park. Its campus grounds are open to anyone without a museum ticket, from 6 a.m. to 9 p.m. daily, with outdoor space, dining, shopping and a Chicago Public Library branch. One branch of the Green Line ends at Cottage Grove station, 800 E. 63rd Street, where the Nos. 4 and 63 buses connect. Daley's moved in 2019 into a new building right at that terminal, a little over a mile west of the Center, in a neighborhood where new buildings had been rare.

Bars and restaurants here

If you run a room on Cottage Grove, you work the blocks around the el stop: a family restaurant that serves dinner early with the overnight hospital shift in mind, a ballroom licensed for entertainment, and a neighborhood spot farther south near 66th. On Stony Island the licensed rooms are inside the Obama Presidential Center. Along 60th Street they sit on the University of Chicago campus, and in Jackson Park the golf course and a lakefront beach spot hold licenses of their own. Corner taverns are few here; the scene runs to kitchens, venues and campus rooms. At least one establishment here has applied with the state for video gaming.