Day 1, March 26: Setting off on holiday with a midday flight offers the advantage of not having to get up early, but in my case at least it also provides me with more time to worry about things. Given that I was travelling alone, I didn’t have to bother anyone else with my concerns, but there were still multiple instances of checking details and sitting in the apartment wondering what I’d forgotten. As it happened, I had missed one tiny detail, but luckily it wasn’t the passport (the only utterly vital item these days).

Courtesy of a much appreciated lift to the airport, my luggage I were deposited in Dublin Airport’s shiny new Terminal 2 with minimal fuss. It was here that I discovered that one niggling detail when I looked at the departures board and failed to find my flight where I expected to: It was actually leaving half an hour earlier. Fortunately, I tend to be overcautious when it comes to giving myself time for appointments, and Terminal 2 wasn’t particularly buzzing that Saturday. The downturn is good for some things, I suppose.

I rattled through the baggage drop and security with no particular problems, but it was a different story when coming up against U.S. security. I’m not sure why the Americans who man these security desks feel that smiling or making someone feel at ease is an unworthy waste of their time, or why they think that slowing things down and making travellers to their country wait a few extra minutes for the privilege is a good thing, but it doesn’t make the process any more fun for those undergoing it. Still, that was the only trouble I faced, so I suppose I can count myself lucky. I was straight onto the plane after reaching the gate and after a short delay I was airborne once more, heading across the Atlantic in the company of three inflight movies and a decent book.

The weather was good for most of the trip across, though Atlantic crossings don’t normally give you much to see. The fact that most of Canada and a good chunk of the northern U.S. were still snowbound did raise concerns that I’d booked my trip a few weeks early, but the snowline was reached just before the crossing of Lake Michigan began, and before long the plane touched down in a chilly but sunny O’Hare airport. Big though it is, it’s easy to navigate, and despite some hassles with ticket machines that are too aloof to offer change, I was soon on the Blue Line train straight into Chicago itself, passing by an eclectic mix of suburban and industrial architecture.

Getting off the train at Clark, I emerged into the City of Big Shoulders. The name seems pretty apt – despite all of the skyscrapers that immediately surround me, there’s still a sense of space and light overhead, with much more elbow room for the soaring edifices than in New York. My destination lies only a few blocks away, on the banks of the river, just south of the latest addition to the skyline: the Trump Tower. Hotel 71 is far from being the most elegant Chicago high-rise, but in terms of location it’s hard to beat, and having paid a little extra for a river view, I got a spectacular look at the city from the 28th floor.

Unpacked, I headed out north across the river. My body was telling me that it was later than it was, but I did my best to stave off jetlag for a while. After some roaming west of Michigan Avenue, I found myself in Fado, an Irish bar. I suppose that counted as acclimatising myself. I only stay for the one drink, noting the basketball on the television that was to prove to be ubiquitous over the rest of my stay. After that, it was on to the Rockit Bar & Grill, a slightly more trendy and upmarket spot, where I got to enjoy beer, good food and some conversation with locals. However, the combination of alcohol and a long day of travelling precluded too late a night, and I’m back at the hotel, catching one last drink at the hotel bar before heading gratefully to bed.

Day 2, March 27: A restless night and a 3,000-mile dislocation combined to see me rise earlier than I might have on a holiday closer to home. Showering and shaving did restore some degree of humanity (thankfully I was hangover free), but as it was a Sunday morning, I was up before most of the city when I went out wandering around the North Loop, just south of the river. There was too much to see right off the bat, so it felt right just to roam at first and take in a city that was just waking up to a clear, bright and very chilly morning.

Bacon and eggs served as a breakfast after I crossed the river, and I swing west to the Magnificent Mile in search of crowds. It’s only around 10am at this point and they’re thin on the ground. It felt a little strange to be seeing the city at this unusual hour, empty and half-awake, but it wasn’t too bad an introduction. I definitely enjoyed the stroll north along Michigan Avenue all the way to the John Hancock Tower, which dominates the northern half of the city centre, with its vast, tapering bulk, decorated with massive x-frames.

I’d been advised that one of the best ways to get a high-rise view of the city was to head to the restaurant and bar on the 95th and 96th floors of the Hancock Tower, so that’s what I tried to do. However, after negotiating a confused queue and a worryingly rickety lift, I found that the bar wasn’t due to open until 11. Regardless, I sneaked up there with a couple of others interested in the view and took the chance to look down on the city – it’s certainly a great view, but the bar in particular is hampered by the massive x-frames on the side of the building, which get in the way of the best vistas.

Rather than waiting until it all opened up (the prices up there are sky-high too) I headed back down to street level, where I availed of a relative’s largesse in the form of a ticket for the Chicago Trolley Tour, which took up the next hour and a half and circled around most of the city center, bounded by the lake and the river on east and west and the Hancock Tower and Soldier Field on north and south. It’s a hop-on, hop-off tour, but I rode it all the way round, enjoying the guide’s encyclopaedic knowledge of his city and obvious pride in its history and especially its famed architecture (something I was to become very familiar with in the days to come).

Hopping off where I’d started from, I made use of a token to pick up a free chocolate bar from the Hershey’s store nearby (the first reminder on the trip that American chocolate is almost inedible), then struck out east, heading for the lake and Lakeshore Drive. The plan was to walk to Navy Pier and continue further south, but the closer I got to the lake, the more bitter the wind got. I was very glad to have packed my gloves and hat – one of the few brave souls I spotted out running that afternoon had a nice pair of socks protecting his hands.

For all that it was cold, it was beautiful out in the sunshine, and reaching Navy Pier gave me my best chance yet to look back and enjoy the skyline. To get to the end of the pier, I had to negotiate a Greek cultural event and slowly growing crowds, and on the way I happened to find the Chicago Shakespeare Theater, which was showing the Druid Theatre Company’s production of Martin McDonagh’s The Cripple of Inishmaan – the last showing of which was that day. Seeing as I’d missed it in Dublin, I changed my plans and grabbed a ticket. In the hour or so I had before the show, I walked to the end of the pier for the full chill-wind-and-sunshine experience, then located a Garretts Popcorn store on the pier for my free (courtesy of a Trolley Tour voucher) sample bag of the Chicago Mix – cheese and caramel in a surprisingly addictive combination.

My review of the play itself can be found elsewhere, but suffice it to say that it’s well worth catching if you can manage it. It might even have been better for the experience of seeing it among a foreign crowd who aren’t necessarily used to such a scabrous view of cliched Irishness. There was still plenty of sun when I emerged from the theatre, so I followed the Chicago Riverwalk back to Hotel 71, again enjoying the fact that I had the place more or less to myself, apart from a few other walkers and joggers.

Already in the first day, I’d seen the towers of the city from above, from below and from a distance. That boded well. Still, I’d done a lot of walking and after an hour back in the hotel room resting my feet, I headed out again, crossing the river in search of cinematic entertainement. That I found in the form of Relentless, which I enjoyed in peace after a meal of gnocchi at P.J. Craig’s bar next door. I just couldn’t bring myself to go for the full American experience of the massive tub of popcorn and gallon of coke. What I could manage was a quiet drink at the hotel bar and some conversation with the friendly staff, and once I was more or less sure that jetlag was no longer a problem, it was time for bed.