The Book of Mormon was playing at the Bank of America Theatre. There were still a few hours to show time, yet the lobby was packed to capacity and the excitement was palpable as the gathered masses, myself included, were ticketless for the sold out show and hoping to win the lottery.
Ten pairs of tickets were up for grabs for the bargain price of $25 and it was the only chance of getting to see the much-hyped production by the creators of South Park.
As luck would have it, my name was not called out so Plan B kicked in. We jumped in a taxi to take us out of the city centre to the northern suburb of Lincoln Park to see a very different kind of musical, the Million Dollar Quartet.
The journey, about 15 minutes by taxi from The Loop, takes you out through the stylish northside of Chicago and to the Apollo Theatre on Lincoln Avenue.
With plenty of time to spare before the show, I took a ramble around the area, where every side street looked to be leading somewhere interesting.
Curiosity drew me towards what looked like a statue of the Tin Man from The Wizard of Oz. On closer inspection, it was the very heartless soul, while his fellow Yellow Brick Road-trippers, Dorothy, the Lion and the Scarecrow, were in close proximity, dotted around the aptly named Oz Park.
There is method to the madness, as the book's author, Lyman Frank Baum, was a resident of the Lincoln Park area back in the late 19th century and the park was officially named Oz Park in the 1970s.
The area is full of great restaurants and bars, giving plenty of pre-show eating options. Bar Forza introduced me to Chicago sliders, basically just a plate full of mini-burgers yet very tasty. The ice cold Italian Peroni beer made for the perfect companion for this quick and easy meal.
The show was an absolute revelation. Not much of a plot, the Million Dollar Quartet is just a snapshot from one night at Sun Studio in Memphis when Elvis Presley, Johnny Cash, Carl Perkins and Jerry Lee Lewis happened to be in town on the same night.
It is more of a concert than a play with each of the musicians at a different stage in their career: Elvis at the top of his game; Cash having just exploded on the scene; Perkins looking to bounce back from his Blue Suede Shoes complex and Lewis a cocky unknown upstart with Sun Studio's latest hit record about to announce his arrival.
The music throughout is exceptional as all four artists deliver stellar performances with Jerry Lee Lewis, played by Lance Lipinsky, stealing the show with a flawless rendition of Great Balls of Fire, complete with crazy, backward piano-playing antics and a voice to match.
I had arrived in Chicago from Memphis where I had just taken a tour around the very same studio. It was a show that would have absolutely completed the Memphis leg of my American road-trip but, as it turned out, proved the perfect start to my Chicago sojourn.
The Windy City of Chicago might imply a feeling of ice-cold winter winds blowing off the Great Lakes through this Illinois city.
And while that would be more than apt from November through February, the name actually derives from the amount of hot air that the local politicians generated in their bid to win the 1893 World Fair. However, locals will tell you that you are not a real Chicagoan until you have lived through a winter.
I needn't have worried. It was mid-summer, blue skies and temperatures pushing towards 30 degrees.
Up early and a 10-minute walk from the hotel took me down to the Lake Shore to marvel at the spectacular Lake Michigan that sprawls out beyond and around towards the adjacent city centre.
Joggers, skateboarders, swimmers and cyclists - this was city living at its best and the definition of my ideal city, where you can live between city and sea (or lake).
The Lake Shore stroll took me right into the heart of Chicago in less than half-an-hour, arriving via the famous Navy Pier, which is a 50-acre fun fair with a range of rides, museums, activities, restaurants and shops, boasting a 150-foot Ferris wheel, which offers great city and Lake Michigan views.
First impressions of this magnificent city will have you hooked within minutes as streets of sparkling skyscrapers are dissected by the ever impressive Chicago River.
You might describe the city as a healthier version of New York with more space, cleaner streets and, perhaps, friendlier folk.
If you like Manhattan, then Chicago will have an immediate effect.
The Loop sits in the absolute centre of Chicago and is the hub of the city's commercial activity. It is also home to some of the finest modern architecture, standing tall and proud on the banks of the Chicago River. And the best way to get to view it and learn is to take the Architecture Boat Tour.
The tour takes you on a journey back to the Great Chicago Fire in 1871 when almost four square miles of the city were destroyed and hundreds of inhabitants were killed.
The riverside cruise takes you past Art Deco buildings telling historical stories through hieroglyphics; towering corn cobs; buildings that are designed to reflect the water; others that pay homage to their older neighbours; not forgetting the monumental Sears Tower (or Willis Tower as it is now commercially known), which was the world's tallest building when it was built in 1973.
The gold-roofed tower that houses the Hard Rock Hotel was designed like a bottle of Champagne, while the jewellers' building included a drive-in elevator for delivery vehicles to protect them from robbery. They were also untouchable due to the fact that notorious local gangster Al Capone was allowed to run a speakeasy within.
Architecture legend Frank Lloyd Wright also made a huge contribution to Chicago and there are many walking tours available to appreciate his work throughout the city.
Despite the dominating skyline, the city's breathability is emphasised by the amount of open spaces dotted throughout central Chicago.
Millennium Park is Chicago's premier green space, located within The Loop, with 25 acres to explore and a range of pretty landscapes, more breathtaking architecture and many art instillations.
But first lunch.
The Park Grill sits in the middle of the park and its open-air terrace is the ideal place to take a break from sightseeing and enjoy a bit of people watching at one of Chicago's most popular attractions.
Portion size might be a problem when you come to these parts – a problem for your waistline, perhaps, as you will do very well to finish anything from the menu.
The turkey, bacon and avocado sandwich was as good as any I have ever tasted but I was ultimately defeated, despite the one or three free Coke refills that I worked my way through. Amazingly, however, no matter how full you get, there always seems to be room for ice cream.
The Cloud Gate instillation is the main attraction of Millennium Park and without doubt it is one of the most impressive modern sculptures that I have encountered.
The Bean, as it is locally known, was inspired by liquid mercury and is made up of 168 stainless steel plates with no visible seams and reflects the Chicago skyline, with every angle offering a different view of the city.
And speaking of the amazing Chicago skyline, one of the top tourist tips is to get an aerial view of the city. The best way to experience this bird's-eye panoramic is to visit the observation decks of either the Sears Tower or the John Hancock Center.
The other option (and a more relaxing and enjoyable experience) is to stop for a drink and a light snack in the roof-top bar at The Wit Hotel on State Street, which sits 27 storeys above the city centre – a classy place full of Chicago's pretty people.
The night moved back towards the hotel to meet up with an old friend and current Chicago resident at The Kerryman on North Clark Street. The Guinness was pouring as it might in John B Keane's pub in Listowel.
I had been on the road for 20 days; it felt like home. Next stop Dublin.
Aer Lingus operates direct from Dublin to Chicago twice daily and is currently offering flights from less than €200 each way. www.aerlingus.com.
For more information about Chicago, visit: www.ChooseChicago.com.
In his next article, Ed looks at where to stay in Chicago and outlines his Top 10 Windy City tourist attractions.