Fly Southwest: MDW to Corning, New York

Ah, the Windy City. Despite its skyscrapers that tickle the clouds and the gloriously greasy deep-dish pizza that it does so well, you've decided to swap Chicago for... Corning. Don't get me wrong, I get the appeal. You're fleeing the urban jungle for the tantalizing twisty glass displays of the Corning Museum of Glass. Now, how to successfully navigate that adventure through Southwest airlines, that's the trick. But have no fear, my jet-setting friend, as your amusingly insightful guide, I am here to bring you nuggets of wisdom with a generous sprinkle of humor.

The first lesson today, class, is to not book last-minute flights if you can. Seriously, folks. It's like trying to grab the last slice of pizza at a party; all hands are on deck, and tensions are high. Plus, your wallet will probably cry. The best time to book your flight is around 1-3 months in advance. Now, if your inner spontaneous spirit decides to take a leaf out of Julia Robert's "Eat, Pray, Love" book, by all means... But be prepared to pay more than the price of the book!

Is economy class your style or are you more of a first-class flyer? Regardless of your preference, Southwest Airlines has you covered. I know, I know, you’re probably thinking, "But where do I put my suitcase full of chicago-style hot-dog souvenirs?". No need to worry about baggage allowance here, my friend. Southwest kindly gives you two free checked bags. Think about all of the pizza and hot dogs you can squeeze into those puppies. As long as your bags don't weigh more than 50 pounds or measure more than 62 inches, we're good to go!

Now I have a riddle for you: how is choosing between a non-stop flight and connecting flights both like a layover and a punchline? Easy! It’s all about timing. Longer jokes and flights with layovers may keep you hanging but deliver a delightful detour (if you enjoy airport bingo, or people watching). On the other hand, those preferring a non-stop service sure know the value of a quick chuckle and getting to the point.

('What's the deal with airline food?' That joke’s still in the works, so stay tuned!).

Allow me to swerve our hovering helicopter back to the frequent flyer crowd. It's not just in-flight peanuts and repetitive viewings of The Fast and the Furious: Tokyo Drift anymore. With Southwest’s mileage program, the more you fly, the more you earn, and the more vacations you...earn! So, it’s like getting paid for sitting; a couch potato's dream come true!

Lastly, and here I don my serious spectacles for a moment, do take some time to read the fine print. This is less of a punchline and more of a lifesaver. Know the flight cancellation policy and your rights. No joke can save you if a blizzard decides to waltz in and paint the town white!

And there we have it. Amid the chuckles and the chortles, we've thrown some light on your upcoming excursion from Chicago to Corning. So, pack your bags (within the allowable limits, of course), rehearse your best 'pretend to be surprised' look when you see the glassworks of Corning, and take off on Southwest Airlines with confidence. Safe travels, comedy connoisseur!