Fly Southwest: MDW to Pittsburgh, Pennsylvania

If you're planning to swap your deep-dish pizza for a tasty Primanti's sandwich and are looking for a fun yet practical way to fly from the Windy City to Steel City, then buckle up buckaroo, because this fun, frolic-filled, and fact-piled guide is just for you.

What's that you're saying? "Oh, but I only fly on Southwest, because only Southwest understands my unique preference for peanuts over pretzels?" That's grand because all the word confetti that’s about to fall is exclusively about flying on the Southwest Airlines. A horizon of blue-and-orange awaits, filled with cheap flights, top-notch in-flight services and a frequent flyer program that may just make Santa feel out-generoused. So hold onto your deep-dish, let's uncover the ins and outs of your upcoming airborne escapade!

Firstly, swapping one food city for another doesn't have to cost an arm and a leg – or even a slice of pizza. Snagging cheap flights on Southwest isn't friend-zoning all the quarters in your wallet. Understandably, you may not be Richie Rich, but thankfully, even Richie wouldn’t find better flight deals than on Southwest – he would just have an easier time nabbing the last-minute flights. Fun Tip: The best time to book the flights is probably while you're loosening your belt post pizza; you've conquered one city's iconic food, on to the next, right?

Did someone say direct flight? Jumping aboard a non-stop service will have you flying high and avoiding layovers like they're awkward conversations. Why the need for any stop, especially when Southwest’s ‘Dom Lawitzke’ (that’s rebranded “Midwest hospitality” for you uber fans) gives you that warm, fuzzy, funny sensation from take-off straight until touchdown. Connecting flights may work if you’re into the dating scene; they are the airfare equivalent of speed-dating after all. They’re also perfect to catch up on the latest airline reviews and silently thank yourself for choosing Southwest. And if enjoying the beauty of nighttime skies sounds appealing, then red-eye flight from Chicago to Pittsburgh is your red-hot ticket.

Bound to have baggage, are we? Whether it's emotional, or something more tangible like a hefty deep-dish pan, Southwest has a baggage allowance policy that doesn't drive you nuts. Remember, packing tips are like doughnuts; it's never bad to have one more, and here's one - Why pay extra for stuffing that souvenir skyline-themed snow globe into your checked baggage when you can hand carry it at no additional cost!? Souvenir in tow, and a few extra bucks saved. Talk about a pizza-pocket full of savings!

Southwest’s in-flight services are a testament to its commitment to ensuring passengers are spirit-finger-level excited throughout their journey. From WiFi that lets you Instagram your pizza-to-sandwich swap to in-flight meals that hold a memorial service for your hunger, these services make sure that your flight duration is less 'when will this end' and more 'do I have to deplane?'

Lastly, join the frequent flyer party! Southwest Airlines' Rapid Rewards mileage program is like your favourite sitcom - you keep returning for more, feeling both loyal and loved. Wave a magic wand, um sorry, your frequent flyer card, and you’ll discover discounts hidden like magical creatures across the Hogwarts … er, Southwest landscape.

So, there you have it, a rollicking round-trip through the jovial journey awaiting you on your Southwest flight from Chicago to Pittsburgh. Now, go ahead, swap that deep-dish for a heap of slaw-topped sandwich and take a bite out of the friendly skies. Safe travels!