Fly Southwest: PWM to Canton, Ohio

Now gather 'round, kiddos, let me tell you the done-to-death, tear-jerking, flight-filled saga of a humble fly-loving traveler, - we’ll call him "Boeing Billy" - embarking on a one-way ticket to Canton from, you guessed it right, none other than the town of hipsters, craft beer, and food trucks: the beloved Portland. Riding high on the wind's back was how Billy lived, spending more than half his life in the sky, always "frequent flyer" on his forehead, chasing cheap flights like kids in a candy store. This time, his trusted steed was the heroic Southwest.

Remember that one friend whose house was never too posh but always welcomed you with open arms and a warm, content smile? Yeah, that's Southwest for you. It’s no first-class fluff or business class bravado airline. It’s more of a "Hey buddy, grab a seat, we have the same airfare for all", kind of friend. So, unless you're a caviar gobbling, champagne chugging creature, Southwest is your comfy, Economy class companion.

But alas! Southwest’s humbleness belies its tumultuous reputation. Infamous for being as punctual as the white rabbit in Alice's Wonderland, Billy often wondered when the 'Flight schedule' was more of a rough guess. "We'll get there when we get there, right?" would resonate through their speaker system. But Billy, bless his heart, always took it with a grain of salt and a dash of airport humor.

As a wise man once said, "There are two kinds of travelers: ones who love layovers and ones who've actually experienced them." Brave Billy was no exception. He could write the book on “layover lemons to lemonade". You see, Southwest may serve its passengers with a helping of unexpected "connecting flights". Much like their offbeat flight schedule, Southwest's path from Portland to Canton isn't necessarily as straightforward as a non-stop run and may add an impromptu layover. You might detour into a whole different state, maybe even a charming no-name town you'd never dream of stopping by.

Now, Billy had developed a sixth sense about the "best time to book" tickets. Just as owls hunt in the night, Billy would be on the prowl for the elusive "red-eye flight." That is, after all, where he had spotted some of the best flight deals. Southwest had indirectly taught him the crucial life lesson: sometimes, the most inconvenient timing can bring forth unexpected treasures.

Despite its ironic sense of punctuality and its habit of throwing itineraries out the window, Southwest always managed to surprise Billy with its “in-flight services”. Expect the unexpected – that’s their unspoken motto. In-flight, you might stumble across an impromptu stand-up performance by a flight attendant, or relish a rap rendition of the safety guidelines. "Buckle up, folks, we're flying down the fast lane!" Ah, the comic relief...

Last but not least, let's not forget about Southwest's other quirk: their renowned baggage allowance policy, also known as "Bags Fly Free". Sure, the name sounds more like a bird liberation movement than an airline policy. But in reality, Billy could bring his proverbial kitchen sink and still have baggage allowance left to spare!

So kiddos, that's the epic ballad of our hero, tasting the skies with Southwest, from the earthy Portland to the faraway Canton. If you find yourself in Billy's shoes, remember - sometimes the journey is way more fun than the destination, and Southwest is sure to remind you of that every step, er...flight of the way!