Questions from the Historic Chicago Walking Bar Tour

Our guides accumulate a lot of knowledge in the course of learning and guiding our Chicago walking tours. Still, we all get questions that stump us from time to time. Being responsible and honest folks, we never fib. Instead, we take the time to do research and discover more about Chicago history. So let’s delve into some Historic Chicago Walking Bar Tour questions!

“Are there any speakeasies still around today?”

Al Capone's Chicago the Green Mill
The Green Mill has been serving booze for over a century, including as a speakeasy during Prohibition. Photo by BriYYZ via flickr.

The most frequent Bar Tour question I field often pops up as we walk away from the fascinating site of Bert Kelly’s Stables. The Stables, a jazz club and speakeasy during Prohibition, didn’t survive until the passage of the 21st Amendment. So folks often ask if there are any speakeasies left. I never really knew, but it turns out a surprising number of speakeasies are still used as bars today. Continuous ownership since Prohibition, on the other hand, is not terribly common.

The Chicago Bar Project has a list of over two dozen bars which were once speakeasies. If a bar was “founded” in 1933, then the odds are it’d been a speakeasy beforehand. That’s the year that the 21st Amendment ended Prohibition and liquor became legal once again. The Berghoff, which studiously stayed within legal limits during Prohibition, has the #1 liquor license in Chicago (as 1893 World’s Fair Walking Tour guests know), but any other Chicago bar that got its license in ‘33 was almost certainly a speakeasy.

Unsurprisingly, some of the oldest bars in Chicago were once speakeasies, like the Green Mill (which we visit on the Jazz, Blues, and Beyond Tour), the Green Door, and the now-departed Schaller’s Pump. It did surprise me to learn, however, just how many little neighborhood bars in Lincoln Park and Old Town, like Burwood Tap, were once speakeasies. These areas are so thoroughly gentrified nowadays that it’s hard to recall they were the scene of much of the gangster violence a century ago.

Capone Conspiracy Theories

Al Capone St. Valentine's Day Massacre
Is this the REAL Al Capone? Probably, yeah.

We get a lot of Bar Tour questions about Capone and the gangsters of Chicago history. Our Private Tour Coordinator Ellen recently fielded a unique one, though. A woman on the tour had heard of conspiracy theories involving the death of Al Capone. The official story is that Public Enemy #1 died of heart failure due to syphilis complications. The legendary mobster apparently had the mental capacity of a 12-year-old due to the infection’s degradation of his brain.

Now, I’m not sure which conspiracies Ellen’s guest had encountered, but some sleuthing on my end turned up a classic. According to this story, Capone was killed in 1929 by his former mentor Johnny Torrio. Torrio then brought Capone’s half-brother from Sicily over to the States and let him be imprisoned by the Feds. This impersonation, not a supposed mental degradation, explains why he never tried to reclaim his spot atop Chicago’s pyramid of gangsters.

A fun story! Almost certainly false, but the thrill of plausibility is what conspiracy theories are all about, right?

“What’s the oldest store on the Mag Mile?”

Every now and then Bar Tour questions come along that you don’t think you’ll ever answer. A year or so ago a guest asked me what the oldest store on the Magnificent Mile was. Friends, I was stumped.

So I took it upon myself to pop into Tiffany’s, which has a corporate history stretching back to the Antebellum Era. I figured such an old and prestigious business was as good a bet as any other. The manager told me Tiffany’s had been selling fine jewelry on North Michigan for over 50 years, but that the oldest continuously-operating store  on the street was Saks Fifth Avenue.

Down the research rabbit-hole I went and, yep, looks like Saks is the answer. Their Chicago location, which was originally located right across the street from the Fourth Presbyterian Church, opened up in 1929. It was their first full-size location outside of New York. For most of their history on the Mag Mile Saks occupied the Art Deco storefronts at 669 North Michigan. So, despite a few moves, this year marks 90 years of operation on the Mag Mile for Saks. That’s crazy!

What’s the story with “Billy Goat” Sianis trying to buy the White Sox?

Billy Goat Tavern Bill Veeck White Sox
The Billy Goat tried to purchase the White Sox? Photo by Amanda Scotese.

Our intrepid Executive Director, Amanda, noticed a letter on the wall of the Billy Goat Tavern regarding their attempt to purchase the Chicago White Sox. Now, a successful restauranteur buying a sports franchise is not the most implausible thing in the world. That is, until one remembers the Goat’s longstanding affiliation with the Cubs. Some historical digging and some conversations at the Billy Goat clarified this mystery.

Bill Veeck was, in his time, a legendary figure in baseball. His father, a Chicago sportswriter, became President of the North Side club when Veeck was still a young man. Indeed, the famous ivy on the outfield walls at Wrigley was Bill Veeck’s idea. In later life, he used the family fortune to purchase several MLB teams, including two stints as owner of the White Sox.

It was during his latter run as owner, which included the famous publicity stunt/fiasco known as Disco Demolition Night, that someone at the Billy Goat had a wise idea. Seems Bill Veeck was a regular at the tavern (see the video with Studs Terkel below), so the Sianis clan had some fun. The Sox were in such poor shape, financially and athletically, that the Sianis clan offered just $20 for the whole franchise. Veeck was a very good sport, of course, as the image attests. Classic Billy Goat story, if you ask me!

– Alex Bean, Content Manager and Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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