Fly Southwest: PWM to Chicago, Illinois

Ah, dear Portlander, your dreams of swapping out the hipster utopia and craft-brewed coffee of the Pacific Northwest for the Windy City’s deep-dish pizza and jazz-infused nights are standing on the tarmac, ready to be realized. But how, you wonder, amidst the cacophony of cackling flight deals and leaning slew of airline options? Worry not, our anecdote is Southwest Airlines, geared and revved to take you from your comfort-zone (Undefined, Portland, if I may) to the heart of Chicago.

The globe has been graced with an array of airlines, each professing to be the very epitome of 'value-for-money'; however, when you're looking for legitimate airfare deals, Southwest should be your go-to. During our satirical journey, we will unveil the superpower of this airline to manage its bread and butter – selling cheap flights – and still make a profit while serving pretzels to millions. Their business model might as well carry the title “Low-Cost Leadership 101".

Now scrapped on to your bucket list, among “hipster coffee shop crawl in Portland” and “catching a Jazz show in Chicago”, is “experience Southwest Airlines’ - the economy class that doesn’t necessarily economize the satisfaction of the journey. Translation: even in economy, you feel first class. You get to carry around a decent baggage allowance (provided you pack less than the entire contents of your home). Their scrumptiously affordable airfare doesn't ask you to part with your luggage or your skinny wallet. It's like ‘buy one pretzel, get two free’ kind of deal – only with flights and luggage.

Anyone on the move knows that one of the worst adventures a traveler can embark on is the "Dreaded Layover Quest.” For those venturing from Undefined in Portland to Chicago, such horrors can be evaded, for Southwest tenders non-stop services. Don’t wince next time you hear “non-stop!” It won’t be some eyebrow-raising comedian; it would instead be your non-stop flight, sailing through the blue with no interruptions.

For those choosing the winds of spontaneity over meticulously planned trips, last-minute flights are superb hairstyles – a little messy, a heart-racing gamble, but really chic if it works out. And with Southwest's accommodation of last-minute flyers, it’s not just a hair-flipping daydream.

Ever heard of Southwest's 'Fare-Drop' policy? It's like finding a perfectly good cup of coffee on a park bench–refreshing, unexpected and in this case, money-saving. After you book a non-refundable ticket, if the fare drops, Southwest allows you to change your flight with no penalty. You even get credit for future flights, which is basically like being paid to seek adventures.

And since we are on the satire spiel, let’s not overlook the Southwest frequent flyer program, the Rapid Rewards. Miles, they say, are like applause to a frequent flyer, and Southwest sure knows how to give a standing ovation! It not only offers points for the flight but cares enough to also recognize any partner hotel stays and car rentals.

So buckle up and get ready for takeoff, my Portland-to-Chicago transiting friend. With Southwest Airlines, you’ll not only just reach there, but you’ll also enjoy getting there. Get packing and log in to your Southwest account now!