Last updated: 11:00 PM ET, Fri July 24 2015

Opinion Home | Far-Sighted Field Notes

  • Rosalind Cummings-Yeates | July 24, 2015 11:00 PM ET

    Gangster's Paradise: 5 Ways To Recapture Chi-town's Mobster History

    Gangster's Paradise: 5 Ways To Recapture Chi-town's Mobster History

    It doesn't really matter that much of Chicago's infamous gangster history occurred nearly 100 years ago, the Windy City will forever be associated with Alphonse Capone and his nefarious peers. Beyond the sheen of Gold Coast boutiques and the lure of top chef restaurants, you'll still find landmarks, attractions and speakeasies associated with much darker times. Here are five ways to dive into Chicago's gangster past:

    Hitch a Ride on Untouchable Tours

    I've experienced many, many tours around the world but none as kooky and fun as this interactive introduction to Chicago's prohibition era crimesters. Hop aboard a black school bus and allow Southside and Johnny Three Knives, decked out in fedoras, spats and suspenders, to guide you through a maze of historical mayhem. With Chicago accents as thick as deep-dish pizza, the guides will make sure you have a kitschy and memorable time. Untouchable Tours has been around for over 25 years, and the two-hour tours regularly sell out so advance reservations are recommended.

    Pay Your Respects At The Biograph Theatre

    Opened in 1914 and a popular movie house until 2004, this historic Lincoln Park cinema arena is now home to the acclaimed Victory Gardens Theatre but the building draws crowds for much more than live productions. In 1934, it was here that John Dillinger donned a straw hat and pin-striped suit to view what would be his last movie. The FBI gunned Dillinger down as he exited the theater and neared the alleyway. As the notorious Public Enemy No. 1, Dillinger's death left a mark on the building, which is listed on the National Register of Historic Places and designated as a Chicago landmark. You can visit the theater at 2433 N. Lincoln Ave, where. Locals say his ghost still haunts the adjoining alleyway.

    Hole Up At The Green Mill

    Opened in 1907, and the longest-running jazz venue in the country, the Green Mill is a must-visit even if you aren't interested in gangland chronicles. But if you are, this nightspot will not disappoint. Noted as a prohibition-era gangster hangout, Jack “Machine Gun” McGurn, a suspected gunman for the St. Valentine's Day Massacre, was a quarter stakeholder in the club.

    McGurn worked for Al Capone, who loved the place so much that he had a special seat across from the side door and special song, “Rhapsody in Blue,” that the band played whenever he entered. The Green Mill hosted performers that included Billie Holiday, Tommy Dorsey and Benny Goodman. Gritty and dimly lit, most of the era's ambiance remains, from the décor and gangster photos behind the bar, to the trapdoor and hydraulic elevator that were used to smuggle in the booze.

    Knock A Few Back at The Drifter

    Over the last two years, speakeasies have re-developed into a popular Chicago attraction, but none boast the prohibition-era pedigree that The Drifter claims. As an adjoining basement to the city's oldest bar, The Green Door Tavern, The Drifter served as a secret storehouse where bootleggers stored the booze to be transferred upstairs to the Green Door. Nowadays, the room is outfitted in original pieces from the period, including circus paraphernalia, a bullet-riddled Pegasus sign and tarot cards that serve as drink menus. There's also a lineup of vaudeville acts including sword swallowers, contortionists and burlesque dancers.

    Bust Into Tommy Gun's Garage

    There's a 1928 Model A Ford, flappers and slapstick humor involved with this musical comedy performance, but if you enjoy corny fun with your gangster lore, this is the place to be. Tommy Gun's Garage's metal door opens to reveal a gun toting gangster demanding a password. Inside, there's '20s music, dancing, skits and a “gangland feast.” The hour and a half show and dinner requires reservations and a high tolerance for silliness.

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Rosalind Cummings-Yeates Far-Sighted Field Notes

Rosalind Cummings-Yeates Rosalind Cummings-Yeates is a journalist, author and blogger who specializes in travel and culture topics. She loves guiding readers through the richness of various cultures and discovering the essence of a destination. Her travel and culture blog, Farsighted Fly Girl, offers travel insights through the music, food, art and history of various countries and cultures. Join her on the journey at www.Rosalindcummingsyeates.
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