It all started with a feral goat that fell off the back of a truck and wandered into a bar. The year was 1934 and Greek immigrant William Sianis took pity on the creature, nursing it back to health.
The two became firm friends and the goat, known as Murphy, was soon a regular fixture at Sianis' bar, which was then called Lincoln Tavern.
Like any self-respecting Chicagoan, Sianis was a massive baseball fan, but when Murphy was ejected from the Chicago Cubs' Wrigley Field Stadium one fateful day in 1945, he was incensed and declared a curse on the team. The Cubs failed to win a World Series for seven decades until it was finally broken in 2016.
Situated under a classic Chicago underpass, the modern-day Billy Goat Tavern, named in honour of Sianis' and Murphy's friendship, oozes history from its walls.
We're here on one of the first stops of a historic bar crawl with Chicago Detours. It's lead by Morgan Lott, a guide whose thorough knowledge of the city is only enhanced by the beer and quartered cheeseburgers a barman has just delivered to our table.
Our group of about a dozen is a mix – some from afar, others from cities in the US, including a group of women from South Carolina with similar haircuts and attire.
Around the corner, we stop outside the site of Bert Kelly's Stables, a renowned jazz club in the early 1900s that was a favourite of Al Capone's.
One night, Capone approached black band leader and clarinettist Johnny Dodds to request a song. The musician feigned ignorance, though in truth he simply considered the jazz standard beneath him and was reticent to oblige. Pulling a crisp $100 bill from his wallet, Capone is said to have torn the note, tucked one half into Dodds' breast pocket and suggested it might be in his best interests if he learned the song before Capone's next visit.
Within a week Capone was back. Approaching Dodds, he pulled his half of the $100 bill from his wallet, prompting Dodds to immediately launch into a fine rendition of Capone's request. "Reflecting on the incident years later, Dodds' son said, 'My father was a man of great principle, but he wasn't an idiot,' " Lott tells us.
Our next stop is the nearby Marriott hotel where we learn more of the city's prohibition history, fittingly of course, over a round of drinks. As we peruse archival photos that tell the story of the temperance movement and key Prohibition moments, Lott peppers us with quiz questions.
The grand prize is nothing more than a salted caramel but it's enough to fire the competitive juices, and when one of the Carolina women emerges victorious, she leaps to her feet, pumping her fists to a cacophony of laughter.
The tour winds up at the InterContinental Hotel on Magnificent Mile, the heart of downtown's shopping district. Built in 1929, it's a wonderful oasis of retro grandeur amid the modern surrounds, like an ornate hall from a period drama.
Drinking wine on the stairwell, we hear outlandish tales of the Shriners, an eccentric fraternity instituted in 1870 and connected to Freemasonry that was influenced by Moroccan iconography. The group once used this venue as a headquarters.With a philosophy rooted in hedonism, they turned the building into a pleasure palace, replete with sword swallowers and belly dancers.
For some, history may seem a dry topic conjuring images of dusty books and drab classrooms. But water it with a few ales, a skilful raconteur and Chicago as a backdrop, and I guarantee, you'll soon think otherwise.
The writer was a guest of Chicago Detours.
Qantas flies several times a week to Los Angeles with connections to Chicago. See qantas.com
The 452-room LondonHouse Chicago is located on the city's river front. See londonhousechicago.com
Chicago Detours offers tours themed around history, architecture, food and drink, from US$36 per person. See chicagodetours.com