What did Chicago’s Biograph Theater, Our Lady of Angels School and the Union Stockyards have in common last Saturday? Any guesses?
All were stops on a marvelous tour entitled “Dark Alleys of Chicago” sponsored by the Chicago Genealogical Society. The focus of the outing was to give local history enthusiasts an opportunity to visit the notorious, infamous and macabre sites that make up the dark side of Chicago’s history. You know ~ the ones you’d never see advertised in those slick advertising brochures marketed to traditional Chicago tourists. And who could resist a tour like that ~ especially in the month of October ~ when ghosts, hauntings, murder and mayhem seem to be the order of the day all month long?

The Biograph in 1934 where John Dillinger, “Public Enemy #1″was finally gunned down by the FBI. (Photo courtesy of the FBI)
Well, I couldn’t resist and neither could my longtime friend Linda Kirsininkas whom I have to thank for the present day tour photos featured in today’s post.
Among our stops? Sites of the St.Valentine’s Day Massacre of 1929; the Biograph theater where notorious bank robber John Dillinger was gunned down by authorities in 1934; and The Four Deuces – the speakeasy, brothel and headquarters run by gangster Al Capone in the late 1920s and early 30′s.
Other points of interest?
Stops and drive-bys included Jane Addams Hull House on the UIC campus; sites of the Haymarket rebellion, the Everleigh sisters turn-of-the-century brothel in the old Levee District, and a stop by the old Chicago stockyards, center of the 1919 labor riots ~ all mere bullet points (no pun intended!) on a very short course in Chicago History.

Our Lady of Angels Catholic school during the 1958 fire that cost nearly 100 lives and changed fire safety codes for schools nationwide. (Photo courtesy of Our Lady of Angels website)
We also passed by Our Lady of Angels school where a devastating fire killed nearly 100 children and teachers in the late 1950s; the street corner where Richard Speck, renowned for killing eight student nurses in 1966, was captured by police; and Washington Square Park where serial killer John Wayne Gacy was known to pick up his victims in the 1970s before completing his ghoulish crimes.

Our Lady of Angels Church today. The school building that replaced the one that burned in 1958 is to the left of the church. (Photo by Linda Kirsininkas)
There are colorful (and lengthy) tales to be told for each site visited last weekend. The photos and captions displayed below, though, will offer a glimpse into some of the fabled stories that dot the Dark Alleys of Chicago.
So please, come along and enjoy this virtual tour into Chicago’s past (that is, if you dare!)
- Our motor coach for the day. I have to give our driver a lot of credit for getting this gigantic buggy up and down the streets of Chicago on a busy Saturday afternoon. (By the way, this bus was 4″ taller than the viaduct we had to retreat from to find another route to our next stop!)
- The Four Deuces as it looked back in the 30s when Capone was king in Chicago. (Photo courtesy of deadlyvalentines.com)
- Site of Al Capone’s former headquarters, the Four Deuces Speakeasy at 2222 South Wabash, a now vacant lot that is loosely cordoned off by some warped cyclone fencing. Back in Capone’s day, the first floor held an antique shop; the second floor was the speakeasy; the third floor was where ladies of the evening “entertained” Capone’s guests; and the top floor served as the gangster’s headquarters where he conducted important business of the day. One tourist asked our guide, Craig Pfannkuche, why the lot was still empty after all these years. The answer? It’s still owned by the mob; there are too many title searches to trace to make it worthwhile; and there are a heck of a lot of back taxes to be paid by someone before the city would ever let it be zoned again for re-use! (Once I heard that lot was still owned by the mob, I skedaddled right back through that fence and got off the property. You never know where these folks may lurk!) (Photo by Linda Kirsininkas)
- Headlines and photos of the Chicago Herald Examiner blast news to Chicagoans of the Valentine’s Day Massacre—the most notorious gangster killing of the Prohibition era. The conflict pitted the South side Italian gang led by Al Capone against the North side Irish gang led by Bugsy Moran.
- This arched entrance way to Chicago’s famous Union Stockyards. Designed by renowned Chicago architects Burnham and Root, this is all that’s left of an era in Chicago history that brings to mind such names as Armour, Swift, “bubbly creek” and Upton Sinclair’s book “The Jungle”, an expose of Chicago’s meatpacking industry. (Photo by Linda Kirsininkas)
- A monument just inside the former Chicago Stockyards commemorating the 1919 and 1920 race riots in Chicago. It bears the names of fallen firemen who lost their lives during that riot. (Photo by Linda Kirsininkas)
- This statue at the corner of Randolph and Jefferson streets commemorates the sites of the 1886 Haymarket Massacre, when German anarchists clashed with Chicago Police over worker’s rights. (Photo by Linda Kirsininkas)
- This sketch of Chicago’s Haymarket riot as interpreted by artists at Harper’s Weekly, spread news of the uprising to readers across the nation.
- This 1886 flyer called for a mass meeting of German anarchists. It resulted in the Haymarket riot, a turning point in Chicago’s labor history.
- The Newberry Library ~ a great resource for genealogists! (Photo by Linda Kirsininkas)
- “Dark Alleys” tourists, Pat Biallas and Linda Kirsininkas relax on a park bench in Washington Square Park across from the Newberry Library ~ an area where serial killer John Wayne Gacy is said to have picked up a few of his unfortunate victims in the 1970s.
- The skyline of Chicago as seen from the South Side. (Photo by Linda Kirsininkas)
- This sign, designating our passage over the reconstructed Randolph Street bridge, offers a tip of the hat to former governor, Rod Blagojevich. (Now that’s one dark alley!) Photo by Linda Kirsininkas
- Chicago’s Dan Ryan expressway where it becomes the Kennedy expressway at Randolph Street. (Photo by Linda Kirsininkas)
- The Biograph in 1934 where John Dillinger, “Public Enemy #1) was finally gunned down by the FBI (Photo courtesy of the FBI)
- Chicago’s Biograph Theater as it looks today. (Photo by Linda Kirsininkas)
- Our Lady of Angels Church today. The school building that replaced the one that burned in 1958 is to the left of the church. (Photo by Linda Kirsininkas)
- Our Lady of Angels Catholic School during the 1958 fire that cost nearly 100 lives and changed fire safety codes for schools nationwide. (Photo courtesy of Our Lady of Angels website)
- Organizers of the captivating “Dark Alleys of Chicago” bus tour: Julie Benson, President of the Chicago Genealogical Society; Stephanie Carbonetti, tour organizer and CGS Program Chair; and the inimitable Craig Pfannkuche, storyteller extraordinaire. Thank you folks, for a very memorable and enjoyable day! (Photo by Linda Kirsininkas)
Copyright © 2012 Patricia Desmond Biallas
























Finally, a tour that gets the Gacy cruising ground right!
Thanks for noting it, Adam. My source was CHS tour guide Craig Pfannkuche.
Good story, Pat! Love the photos.too. I went on a tour of such sites given by my bro in law when I was about 12 years old. At that time I was fascinated with the stories of the St Valentine’s Day Massacre and of course, Al Capone. To see where the action took place in the big city was quite the deal for a small town girl from Adrian.
Thanks, Lorene. Sounds like the perfect age for that kind of a thing!
Pat–What an exciting day you had. That would have been a real adventure, especially since you are so deeply into Chicago history. It made me hope that when I did tours of Detroit the people on the tour got some thrills if not remembrances along the way! Thanks for sending. Dorothy
Fun, indeed. And just as the tour title promised ~ enlightening as well!
Pat: You’re having way too much fun for this to be called work! Enjoy the process. This is fascinating stuff! Diane Desmond
Hi Pat, wonderful job with your coverage of this fun tour. I loved it as much as you. btw, I was the attendee who told Craig that my relatives were “extinguished” by the Capone gang. An interesting story indeed. I have so much information about my Sicilian family and their colorful lives. Great job covering this very terrific CHS event.
Thanks, Sam. Glad you enjoyed the post. That tour was quite entertaining, wasn’t it? Can’t wait to hear about future CGS tours of Chicago.