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Wonder if anyone familiar with travelling this route could comment on whether one or the other may be better, Brandon Toronto via Calgary or via Winnipeg? I would assume via Calgary would be more expensive as far as the fare would go, but possibly you would save on driving to Winnipeg and storing vehicle? Hope someone may be familiar with both routes. thanks.

WestJet is not reliable. We think it’s better to go to Winnipeg to Toronto using air Canada.

the nice thing about air canada and west jet from wpg to toronto is mutiple flights a day and they fly everyday of the week. flair might be a bit cheeper but only one flight a day and there a discount air line. there is also swoop but you fly into hamilton and they are limited on they days they fly in and out.  
 
the main difference between swoop and flair is flight times. swoop has one flight, flair has mutiple but depending on the time of day reall effects the cost

Granted, I have not travelled to Toronto via Calgary from Brandon, but I can outline how I travelled to Toronto last year.  
 
I was really travelling on a budget, though something that I was willing to pay for was convenience, as time is also money. Flying from Brandon to Calgary just to fly all the way back the other way to Toronto seems a little silly to me, especially when we have a really good option to get into Winnipeg without driving with the Brandon Air Shuttle.  
 
I ended up only taking the shuttle on the way home as I had someone willing to drive me to Winnipeg the day I was to leave. You do need to pay to take the shuttle, but the cost is still less than you would need to pay for gas and parking for however long you are away. As well, I appreciated the peace of mind of leaving my car parked at home rather than in Winnipeg.  
 
As far as airline, I flew with Flair. I only took a carry-on bag, and their flight times were reasonable, so it was worth it to me. I did not have any problems with flight delays. If I were to travel to Toronto again, I would likely do it the exact same way. I am curious to see more opinions from people who flew from Calgary however.

Thanks so far for your opinions and look forward to any more that may come up. I tend to agree that using Calgary is the long way around but if fares were close it would be handy to leave from Brandon even if you did have to pass over the Wheat City on the way to WPG!  
I will check the fares both places and see what $$ difference there is.

Fly Brandon>Winnipeg>Calgary>Toronto. Saves time.

You can’t fly to Winnipeg from Brandon but then also if you got to Winnipeg why fly to Calgary? Just go straight to Toronto. It’s a shame the Brandon to Toronto flight didn’t last.

The online listed price for parking at Wpg airport is $20 per day or $90 for a week. Personally I would prefer to have a direct flight than chance missing connections in Calgary, killing time in the airport, paying for over priced airport food etc. Just my opinion but would personally prefer driving to Wpg vs time in Calgary airport

In my experience looking for flights generally the flight there works well going Brandon Calgary to destination. It’s the return flight where it’s quite likely you will need to over night in Calgary. It’s great that we have a flight from Brandon. But for travel to Toronto you are probably best off going from Winnipeg.

I'm not sure if I am any help, but my nephew flew from Winnipeg to Hamilton via Flair or Swoop early April. The flights were on Fridays and Mondays. Hamilton airport is a breeze if you aren't going specifically to Toronto!!!!  
 
Edited by Breber, 2023-04-28 17:02:31

In my experience it has been no contest: Winnipeg to Toronto has been cheaper and is a direct flight. Even taking into account the 2.5 hour drive to the wpg airport and the cost of airport parking, the Winnipeg direct flight has been preferable in my situations.

The additional item people aren't mentioning is the type of plane you wind up on. The flights from Brandon to Calgary are all on a Dash 8, which are much smaller, and are very cramped and uncomfortable, compared to what you will fly on out of Winnipeg.