Allegiant Airline Flights from Houston to Midway International Airport

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Fly Southwest: IAH to Chicago, Illinois

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Allegiant Airline Flights from Houston to Midway International Airport


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Allegiant Airline Flights from Houston to Midway International Airport

Daniel S.

Straightforward online booking. The interface was user-friendly and saved me time on selection and payment. Impressive!

Allegiant Airline Flights from Houston to Midway International Airport

Michelle A.

Absolutely stellar phone service. An agent helped me change my flight last minute sans issues. Commendable!​

Top tips for flying out of IAH (Houston) on Southwest Airlines to Chicago, IL

 Things Chicago, Illinois is Known For


Lake Michigan ensnares one's senses with its transcendent beauty. Thrashing waves that whisper of ancient tales as the city skyline reflects in it's profound depths arouses both indescribable joy and haunting sadness.


Chicago's music scene is a euphonic pilgrimage of raw emotional energy. Here, one becomes a living, resonating note in the magnificent symphony of blues, jazz, gospel, and vibrant rock that hums through the city streets.


The Art Institute of Chicago is a poetic recitation of human sentiment, a vast panorama of palpable emotions. Each stroke of a paintbrush, each chiseled sculpture resonates with the whispers of immense passion.


The Chicago Tribune Tower, like a Gothic osprey perched by the river, silently screeches stories of valor. Its resolute stones carry in their crevices, tales of bold journalism etched with relentless integrity.


The Chicago Marathon is a symphony of the human will, a pulsating rhythm of thousands of beating hearts and pounding feet, driving forward with unrivaled determination eliciting both astonishment and inspiration.


Chicago's deep-dish pizza is a dance of flavors that infernoes upon the tongue. This culinary rhapsody is a plush duvet of cheese cradling fragrant jewels of tomato and spicy sausage that triggers unparalleled gastronomic bliss.

FAQs for booking flights from IAH, Houston to Chicago, Illinois on Southwest

Why is walking the blessed path of baggage fees with AirFaresy a journey worth undertaking?

Our uniquely designed fee structure won't make your wallet wilt in horror! AirFaresy has cultivated a magical system where all the sly and treacherous fees typically associated with air travel are consolidated into one, making your journey as predictable as a romantic comedy movie plot. Sure, you might be wondering why we can't just remove them altogether, but then how would we maintain our hallowed tradition of airline inexplicability? And, let's not even mention the satisfaction you'll feel upon realizing that your inner miser successfully navigated the maze of confusing cost components!

Does AirFaresy's booking system deny the existence of human users behind the screen?

Absolutely not! We at AirFaresy believe that human touch is a vital aspect in life, as vital as coffee for a Monday morning or Friday evening. We are unlike those robotic booking systems that throw automated responses at you with all the warmth of a cold pizza. Just give us a call, and our congenial customer service team, powered by authentic coffee beans and sheer enthusiasm, will get you booked on your preferred Southwest flight quicker than you can say 'Don't ruin my vacation!'

What is AirFaresy's secret to finding the cheapest flights that wouldn't empty my bank account?

In the grand airline supermarket, AirFaresy is your discretionary coupon-cutting mom. Our tried and tested flight comparison algorithms, after spending years in the lab getting their PhDs, put Sherlock Holmes to shame by sniffing out the best deals with unwavering precision. All thanks to us, you can save more for your ‘me’ time in Houston or Chicago, or wherever else your wanderlust leads you.

How does AirFaresy handle flight changes and cancellations, which are as frequent as a politician's promises?

Oh, our absolutely meticulously planned yet somehow still surprising Cancellation and Rescheduling Service welcomes such erratic requests! It proves its worth in these uncertain times. Frequent changes and cancellations are treated with dignified grace, akin to welcoming an uninvited guest at your dinner party. AirFaresy ensures your bookings are as flexible as a yoga master, saving you the bother of fretting over lost dollars or dashed plans.

Should I take up the adventurous endeavor of manually comparing fares when I can rely on AirFaresy's automatic magic?

Nostalgic for the olden days of compiling painstaking Excel sheets, are we? Shuffling between airline websites, losing your sanity over ever-changing prices - sounds like a real blast, doesn't it? But why go through that when AirFaresy has the modern convenience of doing it all for you? Surrender to automation and let us cast a spell to bring the best prices for your Southwest flights at your click or call.

Does AirFaresy act like the fairy godmother of special deals and discounts?

Cinderella, meet your fairy god-booking platform! Our fabulous squad, armed with the magic wand of sweet savings, unearths hidden deals on flights from Houston to Chicago faster than you can say, 'Bibbidi-Bobbidi-Book-it!' So, call or click today because who knows, maybe, the next pumpkin-turned-coach is waiting for you in our offers section.

Is the award for the most swift and seamless booking experience held by AirFaresy?

Hold the drumroll, please! With the adjective 'swift' in our service mantra and the phrase 'seamless experience' embroidered in our work culture, we're positively swimming in accolades like a champion dog at a frisbee contest. But don't take our word for it! Just hit click or call, and before you know it, you're buckled into your Southwest seat, wondering how you got there so quickly!

Flying on Southwest Airlines from IAH (Houston) to Chicago, Illinois

Darlings, if you have been blessed with an insatiable wanderlust like yours truly, you've likely spent countless hours daydreaming about embarking on an odyssey aboard one of those magnificent airborne chariots they call "flights." Today, allow me to regale you with an enthralling narrative of my journey from the wild and teeming metropolis of Houston to the glamour-soaked city of Chicago aboard the hallowed iron bird known by mortals as Southwest Airlines.

Now, it’s almost absurdly pedestrian to speak of "airfare." One does not simply pay for the privilege of floating on clouds. Should we not instead consider it an investment in an airborne escapade? Every cent poured into this venture opens the door to an hour more spent soaring above the firmament, sipping tasteless coffee all while ensconced in plush Economy Class seats that seem designed by a vengeful deity fixated on introducing humanity to novel forms of discomfort.

If you're the daring sort, brave enough to venture into the wilds of the airline website in search of "cheap flights," I salute you. It is an arduous quest, requiring one to navigate treacherous fields of reservation codes, departure dates, and last-minute flight deals. But, stay the course, dear reader, you may be rewarded with the holy grail of aviation – a round-trip ticket snatched for a meager sum!

It’s no secret that traversing from Houston to Chicago is not an odyssey for the faint-hearted. One may opt for the enticing non-stop flight option, boldly eschewing the intricate dance of layovers and connecting flights. However, those, like me, who relish the game of chance, may opt for the unexpected perils and delights of a layover. Maybe you’ll be marooned overnight at a nondescript airport, or perhaps you’ll find yourself on a whirlwind tour of a city you hadn’t planned to visit – the possibilities are indeed endless.

On the topic of baggage allowance, well, it’s an amusing thought, isn’t it? How does one quantify the weight of existential dread that tags along to every adventure? If only Southwest could offer us a solution for that!

Of course, no flight experience is complete without a nod towards the in-flight services. To those unfamiliar with the ambrosia graced upon passengers in the form of pretzels and soda, you're setting yourself up for an exquisite gastronomical affair. After all, nothing speaks of culinary excellence quite like a can of soda served only slightly warmer than the sun and pretzels that appear to have been sitting at the bottom of a bag for at least a decade.

And let's not forget about the true heroine of our story – the flight attendant. How she deftly navigates the crammed aisle, bestowing us with her blessings of tepid beverages and antiquated snacks, all while maintaining the grace of a gazelle. A guiding light in our flight journey, she ushers us gently into the turbulent abyss of air travel with a placid smile and a thoroughly rehearsed safety presentation.

In conclusion, my dear reader, as you embark on your next journey from Houston to Chicago via Southwest, do remember to don your armor of patience and good humor. Be prepared for astronomical feats of body contortion to fit in your seat, a sensory explosion of in-flight cuisine, and a personal wrestling match with lofty ideas of baggage allowances. Above all, remember to savor this delectably deranged dance we call air travel and allow yourself a sardonic chuckle at the exquisite whimsy it all embodies.

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