Living in Saskatchewan comes with a particular problem if you love to travel: getting anywhere can be expensive.
Saskatoon is a relatively small city in a sparsely populated province, which means our options are limited. If you want to travel internationally, there’s a very good chance your first flight isn’t really taking you toward your destination. It’s taking you somewhere with more flights. Toronto. Calgary. Vancouver. Minneapolis. Denver. Then your trip can actually begin.
Earlier this summer, while casually browsing Google Flights (as I am wont to do) I started noticing something strange. Every once in a while, flights leaving Saskatoon within the next 24 hours were incredibly cheap. Not cheap by Saskatchewan standards. Actually cheap.
That gave me an idea. What if, instead of choosing somewhere to go and then trying to find an affordable flight, I did the exact opposite? What if I waited until the last possible moment, found the cheapest international flight available, and let the airfare decide where I was going?
There would be two rules. First, it had to be the cheapest round-trip fare I could find. No cheating with a $200 flight somewhere followed by a $1,700 flight home. Second, the journey had to be under 20 hours each way. I was willing to make some questionable decisions in the name of travel, but there had to be a limit somewhere.

My friend Spencer agreed to join me. He had five days free at the end of August, so we picked the dates and then did something that goes against pretty much every instinct I have when planning a trip: nothing.
In the weeks leading up to it, I kept checking what would happen if we left that day. Nassau appeared. London. Mexico City. One day, inexplicably, Singapore. But as the actual departure date got closer, one destination kept appearing near the top: Reykjavík.
Iceland had always been somewhere I wanted to visit, so this seemed almost suspiciously perfect. We’d probably have three or four days once travel time was removed. Not enough to see much of the country, but enough for Reykjavík, a road trip, some waterfalls and the inevitable experience of being financially humbled by lunch.
I started to assume Iceland was happening.
Then booking day arrived and the cheap flights disappeared.
The fares out of Saskatoon had been creeping upward for weeks. Trips that had once been appearing for around $500 round trip became $800, then $1,000, then $1,200. By the time we actually needed to book, some were pushing $1,500.
This experiment was becoming significantly less fun.
Then I remembered Regina. It’s about a two-and-a-half-hour drive from Saskatoon, but it has something Saskatoon currently doesn’t: United Airlines service to the United States. That opened up an entirely different network of flights.

I changed the departure airport.
The prices dropped.
And there it was: Dublin.
For a little over $1,000 round trip, we could fly from Regina to Denver, Denver to Chicago, then overnight from Chicago to Dublin. It was not exactly a direct route, but that was hardly the point. We were going to Ireland.
We would leave Regina around 9:30 the next morning, roughly 19 hours after booking the tickets, and arrive in Dublin at 9:50 a.m. the following day. We’d spend about three days in Ireland and then come home.
Perfect.
We packed, finished as much work as we could and, around 10:30 that night, Spencer picked me up in Saskatoon. We drove to Regina, arrived at my mom and stepdad’s place around 1 a.m., slept for a few hours and headed to the airport in the morning.
For a while, everything went suspiciously well.
We made it to Denver. Then our flight to Chicago was delayed. Then delayed again. Our comfortable two-hour connection in Chicago became an hour, then half an hour, then about ten minutes.
We started looking for alternatives. Could United send us through Newark instead? Was there another way to Dublin that night? Could we somehow convince the laws of time and space to cooperate?
No luck.

Eventually, we boarded our original flight to Chicago. There was still a tiny chance that if we took off immediately and made up some time in the air, we could sprint through O’Hare and catch the Dublin flight.
And of course, as luck would have it, we did not take off immediately.
A storm was moving through Denver and departures were stopped. So we sat on the tarmac. And sat. By the time our plane finally took off, we had been sitting there for more than two hours.
Our flight to Ireland had left Chicago before we had even left Colorado.
There is something particularly funny about booking a trip less than 24 hours before departure and then almost immediately losing 24 hours of it.
While we were stuck on the plane, I was messaging United support trying to figure out what happened next. They could put us on the same Chicago-to-Dublin flight the following evening, which solved one problem and created another. When your entire trip is only supposed to include about 72 hours in Ireland, losing 24 of them is fairly significant.
So I asked if, since we were arriving a day late because of the delay, they could also move our flight home back by a day.
I fully expected the answer to be no.
Instead, they did it.
Suddenly, we weren’t losing a day in Ireland. We were gaining a day in Chicago.
United provided us with a hotel outside the airport, and we finally got there close to 1 a.m. The next morning, we woke up with almost an entire day in a city neither of us had planned to visit.
So we went sightseeing.

We headed downtown to Millennium Park because obviously, if you accidentally end up with one day in Chicago, you have to see the Bean. We walked to Buckingham Fountain and along Lake Michigan, wandered beside the Chicago River, stopped for a cider and looked up at the former Sears Tower. At some point, I also bought what may have been the most expensive frozen lemonade ever slushed.
It was actually a great day.
Then we headed back to O’Hare, boarded our second attempt at a flight to Ireland and, this time, left the ground.
We arrived in Dublin the next morning.
I won’t turn this into a minute-by-minute account of Ireland because, strangely enough, the part of this trip I keep thinking about is everything that happened around it. But the 72 hours we did have there were packed.







We wandered around Dublin, ate in pubs and had some truly excellent meals, including a lamb shank and mash I am still thinking about. We drank Guinness at the Guinness Storehouse, toured Trinity College and saw the Book of Kells, went out to Temple Bar and took a day trip across the country to Galway and the Cliffs of Moher.
It was exactly the kind of quick introduction to Ireland I had hoped for.
And then, almost immediately, it was time to leave.
The trip home took us from Dublin to Washington, then Denver, then Regina, followed by the two-and-a-half-hour drive back to Saskatoon. We finally pulled into the city around 2 a.m.
All told, we had been gone for six days. We had spent roughly 72 hours in Ireland.
Which raises the obvious question: was that worth it?
Even the border officers seemed unsure.
“You went to Ireland for three days?”
Yes.
“And now you’re coming home?”
Yes.
I understand why some people would look at the itinerary and think it sounds ridiculous. We spent a huge amount of time in transit. We crossed the Atlantic twice. We drove between Saskatoon and Regina twice. We missed a flight, got stuck overnight in Chicago and probably spent almost as much time moving between places as we did actually being in Ireland.
But I’d do it again.

What I liked about this trip was that we gave up almost all control over what it was supposed to look like. A few weeks earlier, we had no idea what country we were going to. Nineteen hours before departure, we learned it was Ireland. Halfway there, we learned Chicago was apparently part of the itinerary too.
There was no perfectly optimized schedule, no months of planning and no attempt to see absolutely everything. We just went.
And somehow, in six days, we got an unexpected day in Chicago, three days in Ireland, a trip across the country to the Cliffs of Moher, nights in Dublin pubs, a lot of airport food, several increasingly complicated conversations with United Airlines, and one of those trips that became memorable partly because it kept refusing to go according to plan.
Would I recommend flying from Saskatchewan to Ireland for only 72 hours? Probably not as the most efficient use of your time.
Would I do it again?
Absolutely.
Because sometimes the opportunity is worth more than the perfect itinerary.
And sometimes the trip you didn’t plan properly ends up being the one you talk about for years.