There is always one important question that comes before every great getaway, and kicks off the adventure itself: “How are we getting there?”

As Editor-in-Chief of datenight, I spend a lot of time discovering experiences worth travelling for; from festivals and annual events to hotel stays, city escapes, and bucket-list adventures across Canada. But before I can plan where I’m eating, what I’m seeing, or which experiences make the itinerary, I have to figure out the logistics first… and it’s a bigger part of the job than you might think.

This summer, I finally checked something off my personal and professional bucket list: experiencing the Calgary Stampede for the first time!

With Calgary being one of our biggest markets and datenight’s Western Canada Editor, Mackenzie, based there, I’ve travelled to the city many times for work meet-ups and winter trips, but the Calgary Stampede is one of those iconic Canadian events I’ve always wanted to experience.

Once my travel dates and stay were confirmed, the next step was figuring out how to get there, which, during Calgary Stampede season, isn’t always the easiest feat… and that’s where I started planning my flight using Skyscanner.

Planning a trip around a major event starts with the flight

The Calgary Stampede is one of those events where planning ahead really matters. Every July, Calgary transforms into one of Canada’s biggest destinations, with visitors travelling from across the country and around the world for rodeo events, concerts, midway food, parties, and the famous Stampede atmosphere.

With visitors searching for flights to Calgary Stampede months in advance, planning your transportation early can make a huge difference, and because so many people are travelling at the same time, flights and accommodations can become more expensive as the dates get closer.

I knew my travel dates were July 6 to July 9, since I had commitments before and after the trip, and I wanted to maximize my time in Calgary without extending the trip too much. Since I was travelling during one of the busiest times of the year, I knew I needed flexibility within those dates.

My first step was searching Toronto Pearson (YYZ) to Calgary International Airport (YYC) on Skyscanner.

What I liked immediately was that instead of checking multiple airline websites separately, I could compare different airlines, departure times, routes, and prices all in one place.

For someone balancing a busy work and personal schedule, saving that time is a huge part of the appeal.

Finding the right flight for me (not just the cheapest option)

When I’m planning travel for datenight, the cheapest option isn’t always automatically the best option. For me, time really matters.

Especially when you’re travelling for a major event.

For my Calgary Stampede trip, I wanted to arrive early enough to actually enjoy my first day and leave late enough on my final day that I wasn’t wasting valuable time during events at the airport and travelling. Using Skyscanner’s filters and sorting options, I was able to compare flights based on what actually mattered to me:

• A direct flight
• A morning arrival into Calgary
• A late evening departure home
• A schedule that allowed me to maximize my time in the city

I ended up finding two WestJet flights, presented as a bundled round-trip option, that worked perfectly for my schedule. My flight from Toronto left at 6 a.m. and arrived in Calgary at 8:20 a.m. – just in time for one of the city’s famous Stampede pancake breakfasts.

After landing, Mackenzie picked me up from the airport and we headed straight to the Telus Spark Dino Pancake Stampede Breakfast, which was the perfect way to kick off the trip.

For my return flight, I left Calgary at 7:10 p.m., giving me almost a full final day in the city before heading home.

That was exactly what I wanted from the trip: more time experiencing Calgary, no checking out early, and less time sitting around waiting for flights.

Why I like comparing flights before booking

One of the biggest things I appreciate about using a platform like Skyscanner is being able to actually see my options. When you search through one airline website, you’re naturally limited to that airline’s schedule. Then repeating that for multiple airlines is just so much extra work and time spent.

When you’re comparing multiple airlines at once, you can find combinations you might not have considered or found before. For my trip, I compared options from airlines including WestJet, Porter, and Flair. Ultimately, WestJet made the most sense for me based on the flight times and overall experience.

But the important part was having the ability to compare everything first.

Another feature I found helpful was being able to look at nearby dates and see how prices changed. If you have flexibility, even moving your trip by a day can sometimes open up different options or better prices. For events like the Calgary Stampede, TIFF, music festivals, sporting events, or concerts, those small adjustments can make a big difference.

A common myth about booking platforms (busted)

One thing I was curious about before booking was whether using a flight search platform would make the experience more complicated once I actually had my ticket. Would I still be able to access my airline booking? Would I still get updates? Would I be able to manage my trip normally? The answer was absolutely, yes.

After booking through Skyscanner and being connected to the ticketing platform, I received both my booking confirmation and my WestJet confirmation code, allowing me to manage my trip directly through both the ticketing platform and the WestJet app.

I could check my flight details, access updates and notifications, and use the same airline tools I would have used if I booked directly. The entire process is completely seamless.

Experiencing the Calgary Stampede

Once I arrived, the trip was everything I hoped it would be.

I stayed at The Dorian Hotel in downtown Calgary, which was the perfect location for experiencing Stampede week.

Being downtown meant I could easily walk around, explore different neighbourhoods, and hop on Calgary’s transit system to get to the Stampede grounds in a mere three stops.

My hotel room even overlooked Wildhorse Saloon, one of the Stampede-related venues downtown, which made it feel like the entire city was celebrating around me.

During my visit, we packed in as much as possible, like watching the Chuckwagon races, experiencing the evening show at the Stampede grounds, exploring the midway and trying some of the wild Stampede food offerings, visiting Nashville North and other Stampede entertainment venues, walking through downtown Calgary during Stampede week, and checking out patios, cafés, and local spots around the city!

Of course, because datenight is all about finding memorable experiences, we had to try some of the iconic Stampede food too.

Some of the highlights included deep fried watermelon, maple bacon cheese curds, Korean beef pierogies, taco in a bag, and the famous foot-long midway french fries.

The energy of Calgary during Stampede is unlike anything I’ve experienced before. The entire city shows up for it, from the western outfits everywhere you look to the nightly 11pm fireworks at the grounds.

Planning future Canadian event trips

The Calgary Stampede was a great reminder that some of the best travel experiences in Canada are tied to events. Travelling for a festival, concert, sporting event, or annual celebration… the flight is often the first thing you need to figure out.

At datenight we regularly plan trips around experiences like fairs and festivals, concerts and sporting events, holiday markets and so much more!

These experiences are often the reason people travel for their date night getaways, but planning the logistics early makes the entire trip easier.

My biggest advice? Don’t wait until the last minute if you already know you want to go.

Book your flight early, track prices, compare your options, and give yourself more room to plan the fun parts of your trip, whether that’s a nicer hotel, a special dinner reservation, or an unforgettable experience.

And if you do find yourself planning closer to the date (like I did), don’t assume you’re stuck with whatever option appears first. Take the time to compare. There may still be a route, price, or schedule that works better than you expect!

For me, travel has always been about the experiences waiting at the other end – meeting up with our team across the country, discovering a new city, attending an iconic event, or finding the next great date idea to share with our readers.

The easier the logistics are, the more time there is to actually enjoy the reason you travelled in the first place.