Alaska Airlines from Midway International Airport to Portland

So, you're jetting off to the luscious green wilderness of Portland from everyone's favorite windy runway, Midway International. As luck would have it, you're about to clutch onto the metaphorical tail of the often-overlooked pegasus, Alaska Airlines. Why don't you brace yourself for a whimsical journey that promises to be as thrilling as watching paint dry?

Let's choose our poison, shall we? One-way or round-trip? The latter seems like a brilliant way of converting a mini-holiday into an epic saga featuring overpriced economy-class seats and re-runs of sitcoms so old, they feature jokes about Blockbuster's latest releases. On the other hand, after being serenaded by Alaska's in-flight services, you might be so entranced that you'll voluntarily choose one-way and establish a quaint, umbrella-laden existence in Portland.

But, let’s talk about the flight duration for a moment. The non-stop—ah, music to any traveler's ears—flight has an average duration of about four hours, while the connecting flights could have you enjoying Midway's rather delightful layover facilities. So, you'd have a generous slot of time to contemplate your life choices, perhaps like your decision to not book a first-class ticket when you had the chance.

Oh, and let's not forget about the subtle nuances of the airfare game—or should I brand it as the ‘Flights of Fortune’? See, here's the magic formula: The best time to book is when your instinct, aligned with the cosmic divine, sends shivers down your spine screaming "Eureka!"—or, you know, a Tuesday.

Now, if you're a seasoned traveler—an ambassador of the arcane art of globetrotting—you have probably flirted with the idea of becoming a frequent flyer. With Alaska's mileage program, you could potentially unlock infinite, unprecedented, undiluted power - or, a discounted muffin and coffee at the airport café. Yes, the Mileage Plan will grant you royalty perks befitting an economy class monarch.

And what about your baggage allowance? Well, prepare to enter a world of regulated chaos where the ability to push suitcases into tiny, impossibly fitted overhead lockers becomes the ultimate power move. Forget it, and you might find your beloved "small" carry-on relegated to the mysterious, cavernous world of cargo holds.

Oh, and here's a mesmerizing gem about Alaska (the State, not the airline). Did you know that Alaska is the only state capable of typing out its entire name on one row of a standard English QWERTY keyboard? Alas, the excitement is heart-stopping.

In reality, Alaska Airlines is well-loved for its punctuality and helpful staff. The direct flights are a godsend when you’re just itching to say hello to Portland’s bridges. The airline reviews reflect their quality services in bright, glowing terms, as shiny as the steel cutlery that you wouldn't find in the economy class.

So, hold on tight and keep your eyes peeled for the divine dance of the Northern Lights, or perhaps the scenic beauty of Portland, if indeed, with affirming courage, you have decided to open those window blinds mid-flight. Bon Voyage, traveler. Don't forget to cling to this narrative of thrill, excitement and action-packed adventure cruising at 30,000 feet above sea level, carried forth by the quiet efficiency of—no drumroll, please—Alaska Airlines.