The river is a glistening emerald green in the Windy City, Chicago Da Pope Town, and they’ve not even had to resort to their signature St Paddy’s Day dye.
The mile-long Riverwalk is where the locals come to catch the wind on baking hot summer days like today.
On extended liquid lunches, work functions or simply sinking into deckchairs.
And maybe grabbing an ice from Downtown favourite Sweet Home Gelato or join the party at O’Brien’s Riverwalkhttps://www.obriensrestaurant.com Cafe.
An L of a Riverwalk
A green kayak winds its way under one of the ubiquitous steel and concrete bridges which dissect the skyscrapers.
The L, the name for the inner city elevated trains we know from the Blues Brothers and countless other movies, rattles across it.
And the queues form on the jetties for the party boats.
All set to take Chicago newbies, like ourselves, onto the river and through the flow of the Second City’s history.
ing Architecture River Tour to the edge of Lake Michigan.
The two hours breeze by as we learn how Chicago’s modern skyline formed.
Second City vibes
Each building on from the most recent architectural breakthrough, including, er Trump Tower.
The Second City mantle, locals will tell you, is no deference to New York, the only city larger in the whole of the union.
But rather a reference to the Great Fire of 1871, with the skyscraper city we see today, the successor to the original settlement.
It’s not all big city rivalry though which we see for ourselves at The Second City comedy club.
With today’s improv stars tipped to follow in the footsteps of the pioneers.
Towering ambitions
Those who went on to make Saturday Night Live in New York a worldwide hit.
Back on the architecture tour we learn that locals still argue.
That their Sears Tower, or Willis Tower, should still be classified as the highest skyscraper in the US.
Whatever the arguments you will enjoy the best views of the city from the Skyview.
The highest observation tower in America, atop the 1,451ft Tower.
Your ears will probably pop and not just because everyone on the meet and greet line is Irish on their J1er.
O’Leary’s band
We really do get everywhere in this city.
Though not always for the right reasons.
An Irish immigrant Mrs O’Leary gained ignominy as the 1871 fire starter after her cow Daisy booted a pale over.
Setting off a chain of events which saw the majority of the city’s wooden houses torched.
Only the poor woman was falsely maligned because of anti-Irish feeling at the time.
And alas she was not exonerated until nearly 150 years later, long after she herself had kicked the bucket.
While poor innocent Mrs O’Leary’s name was blackened, Alphonse Capone spawned a gangster tourist industry on his back.
Al Capone and Speakeasy Chicago
We see it in the merch stores and bars all over Chicago.
And for research purposes, you understand, we sample cocktails in Pohttps://www.potterschicago.comtter’s Bar.
A prohibition-themed drinking hole in our billet the Palmer House a Hilton Hotel.
Just a 20-minute walk or ten-minute or L ride to the river.
Chicago’s speakeasy history takes an unexpected turn later in our five-day break.
When we explore the city’s neighbourhood, and specifically bohemian Andersonville.
And we are magically transported out of a laundromat into the world of the Chicago Magic Lounge.
Where we are treated to a Chicago-style magic bar show and cocktails.
Including the intriguing How Houdini Died, their take on rum punch.
The Windy City
Chicago, the Second City, The Windy City (on account of its politicians, rather than any gusts off the lake).
It also goes by the moniker City of Broad Shoulders.
Evidenced by how the Chicagoans rebuilt their city to the status it holds today, the original Skyscraper City.
And how its citizens overcame adversity.
Not least it’s LGBTQ+ community.
ChicaGay revisited
It is Pride Month when we visit in June.
Chicagoans are rightly proud that their Pride March is the world’s oldest predating New York’s and Los Angeles’s by a day.
We have come to the community’s hub, the Gayborhood of North Halstead Street.
To a Chicago entertainment institution, Sidetrack, a multi-bar multi-cultural meeting place.
Renowned for its inclusivity, cocktail slushies and drag nights.
We roll out late but refreshed and bouncing for our train journey back into Downtown.
Home run
We mingle with the sports fans trooping out of Wrigley Field, the second oldest baseball park in the US.
And grab a Chicago Hot Dog, greened up with relish and gherkins.
While Chicago deep-dish pizza are staples too for baseball fans.
The stallholders around Wrigley Field are selling T-shirts of the city’s Pope in shades.
Holding a Chicago hot dog and craft beer he might have bought in Murphy’s Bar.
The City of many faces and names has his and our blessing and a new title Chicago Da Pope Town.
Jim flew to Chicago Da Pope Town. with Aer Lingus from Dublin with pre-clearance from €800 and stayed at the Palmer House Hotel from €287 per night.
This article was published in the Irish Daily Mirror on July 26, 2025.