Fly Southwest: MDW to Tulsa, Oklahoma

Oh, wondrous travelers seeking the thrill of traversing the skies from the undefined heart of Chicago to the lush expanses of Tulsa! Rest assured, your quest is both noble and fraught with challenges that would make even the most jaded airline captain quiver in their high-altitude boots. Yet, in the spirit of delivering unvarnished facts and cutting-edge advice, I shall stand as your faithful guide through this odyssey.

The object of our mirthful scrutiny, Southwest Airlines, likes to drape itself in a cloak of unrivaled flight deals and airfare with such audaciousness that would make even a peacock blush. They offer a veritable cornucopia of choices - from one-way odysseys for the spontaneous spirit, round-trip sojourns for the traditionalist, to the red-eye flights for the nocturnal adventurers. Navigating these options is akin to a knight's quest for the Holy Grail.

Now, the noble reader might be considering, "Direct flights or connecting flights? To layover or not to layover?" A conundrum indeed, of Herculean proportion! Should you wish to indulge in a non-stop airborne sprint across the states, be prepared to part ways with your hard-earned treasure. Alas, for those of us less willing to squander our fortunes, a judicious layover could indeed prove frugal.

The cagey traveler might save a king's ransom with last-minute flights, but beware the capricious airline's flight cancellation policy, as tempestuous as a summer storm hovering over the Great Lakes. Ah, but remember, Southwest's "No Change Fee" policy, which like a benevolent monarch, allows subjects to alter their flight schedule without reaching deep into their coffers.

I hear pennies being pinched anxiously as I broach the topic of baggage allowance. The frugality of Southwest's policy, which accommodates two free checked bags, is as remarkable as the Great Wall visible from space - a fact often twisted into marketing hyperbole with a dexterity that would make a contortionist green with envy.

What more is there to ponder? The echelons of flying, draped in the mysteries of the enigmatic terms: Economy Class, Premium Economy, Business Class, and the crown jewel, First-Class! But do not be swayed by their radiant allure, dear reader. Southwest flies democracy, just one class, devoid of hierarchical trappings. Like a Robin Hood of the skies, it resists the allure of unnecessarily complicated class systems.

Lest we overlook the siren call of the Frequent Flyer Program, the Rapid Rewards® program boasts enticing benefits. Consider this a maritime warning though, dear reader - these miles are quick to seduce, but could leave you bobbing in the turbulent sea of fine prints and blackout dates.

When is the best time to book, you ask? The answer, my dear traveler, is as elusive as the Northwest Passage and entirely dependent on the whimsies of economic market forces too convoluted for our modest discourse. Yet the adage remains: The early bird catches the worm.

Spanning intriguing domestic flights to more exotic international flights, Southwest beckons you, like Ulysses dashing daringly into Neptune's billowing embrace. It’s an airline that exacts a dash of daredevil spirit that renders the journey as thrilling as the destination.

Fear not the labyrinthine flight duration or in-flight services that promise Marie Antoinette’s decadence at Noah's Ark's budget, dear reader. Instead, prepare your spirit for the exhilarating jaunt across the heavens, as we embark from the rallying cries of the 'Windy City' to the charming domain of Tulsa — aboard the jesters of the sky, Southwest Airlines.