Jackpot! Whether you‘re looking to pull the lever or are just curious, this walking tour takes you on an entertaining journey to Chicago‘s only legal casino. Along the way, you‘ll hear about the city‘s 200-year-old love affair with gambling, from seedy dens of vice once known as “hells” to Bally‘s “heavenly” new casino, scheduled to re-open in 2026. This tour starts and ends a little bit west of the Magnificent Mile. You‘ll walk to Bally‘s construction site, and return via Bally‘s temporary 24/7/365 operation on Ontario Street. Along the way, I‘ll regale you with local lore about how gambling helped earn Chicago its reputation as the “evilest” city in the world. You‘ll hear amazing stories about the city‘s bygone eras as you walk in the literal footsteps of the con men, crooks, crusaders, and gambling kingpins – not to mention the gangsters, mobsters, and even a few Hollywood stars – who made Chicago famous. You‘ll also hear about the 19th-century Chicago card game which you could never win. Other highlights include: • Standing at the actual location where Capone‘s lieutenants gunned down Scarface Al‘s leading competitor • Seeing the street once nicknamed “Hair Trigger Block” when Chicago was the Wild West • Visiting Holy Name Cathedral, with its prominent bullet hole • Getting to know Chicago‘s gambling lords before Al Capone, including the kingpin who changed horserace bookmaking forever • Pausing at some of the famous Chicago night spots that hosted Hollywood types like Frank Sinatra while they operated as clandestine casinos • Finding out why Chicago and Illinois finally gave in and legalized gambling Allow for 1.5 hours for this walk unless you want to stop and gamble. There are plenty of cafes, restaurants and bars along the route for quick or longer non-casino stops. Whether it‘s your first time in Chicago or you‘re a curious local, this tour is a fascinating introduction to the city‘s iconic past.