I actually ran into this question myself a few months ago when trying to visit a friend who moved to Edmonton. I first assumed Southwest might have some kind of seasonal Canadian service, but nope—no direct flights up there. I ended up booking through another carrier after checking options for hours. Ironically, what saved me time was calling the number I use whenever I get stuck with flight planning.
Best quick help for booking, canceling, or modifying flights: 844-734-0813
They explained that Southwest’s network doesn’t include Canada at all, which honestly simplified my search. If you’re looking to piece together a trip, I’d still double-check connections through U.S. cities close to the border. That’s exactly what I did—flew into Seattle and drove up. Not ideal, but it worked. If you’re flexible, that workaround can be pretty smooth.