Allegiant Airline Flights from Dallas to Midway International Airport

Affordable flights are a call away!

Affordable flights are a call away!

Fly Southwest: DAL to Chicago, Illinois

Get Huge Savings! Call now to unlock exclusive and unpublished deals.

Allegiant Airline Flights from Dallas to Midway International Airport


Call us anytime - day or night - and speak to one of our agents right away. No waiting and no hassle. Don't hesitate, call now.


Our tireless efforts result in securing unbeatable deals from a vast network of airlines. Get the best value for your money with us.

BEST Travel FlexibilitY

Need more flexibility in your travel plans? No problem. We've got you covered with our flexible options.

+ Add Return Date

Search Now

Allegiant Airline Flights from Dallas to Midway International Airport

Jonathan A.

Wonderful online booking experience. It was quick, efficient, and no hitches at all. Will use again.

Allegiant Airline Flights from Dallas to Midway International Airport

Brian G.

Superb customer care over the phone. Made my last-minute changes stress-free. A service to rave about.​

Top tips for flying out of DAL (Dallas) 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 DAL, Dallas to Chicago, Illinois on Southwest

What are the current fare details for a Southwest flight from Dallas to Chicago on AirFaresy?

On AirFaresy, we offer comprehensive fare information with real-time updates. As of now, Southwest fares for a flight from Dallas to Chicago are competitively priced. However, due to demand and season, fares can fluctuate. We recommend you to check the fares regularly on our platform or contact our customer service for the most accurate and current information.

What’s the best time to book a flight from Dallas to Chicago on AirFaresy?

The optimal time to book a flight usually depends on a variety of factors including time of year, day of the week, and how far in advance you book. On AirFaresy, we make it easy for you by offering a 'Low Fare Calendar' feature that shows the cheapest days to fly. We encourage travelers to be flexible with their dates for securing the best fares.

What are the baggage policies for Southwest flights booked through AirF aresy?

Southwest Airlines allows two checked bags for free, with a weight limit of 50 pounds and size limit of 62 inches each. There are also provisions for a personal item and a carry-on bag. Make sure to check the specifics on Southwest's baggage policy on our site to avoid any surprises during your trip.

How does AirFaresy handle flight cancellations or changes for Southwest flights?

At AirFaresy, we assist our customers through all phases of their travel journey. In case of flight cancellations or changes, we facilitate processes as per Southwest's flight change policy, ensuring minimal disruption to your plans. Moreover, AirFaresy's personalized customer service is available round the clock to address your concerns.

What facilities and amenities should I expect on a Southwest flight from Dallas to Chicago booked through AirFaresy?

Southwest Airlines are known for their customer-friendly services. You can expect in-flight amenities like free live TV, WiFi at a small cost, and complimentary snacks and drinks. For detailed specifics of what's offered on your flight, the AirFaresy website or customer service will be happy to help.

Does AirFaresy offer any discounts or special deals for Southwest flights from Dallas to Chicago?

Yes, AirFaresy regularly features exclusive deals and offers for various flights. For Southwest flights from Dallas to Chicago, you can check the 'Deals' section on our website or subscribe to our newsletter to stay updated on the latest discounts.

How does AirFaresy ensure safety and hygiene on Southwest flights during the current pandemic?

AirFaresy is deeply committed to the safety of all passengers. We adhere to all airline and health advisories. Southwest Airlines has implemented stringent health measures such as deep-cleaning practices, HEPA filters on planes, and mask requirement for all individuals onboard. For more specific safety concerns, feel free to contact our customer service or visit our website.

Flying on Southwest Airlines from DAL (Dallas) to Chicago, Illinois

If Shakespeare were a frequent flyer on Southwest Airlines, writing odes in the skies from the bustling heart of Texas, Dallas, to the sprawling metropolis of Chicago, he might wax poetic about its offerings. Whether it's the tantalizing promise of cheap flights or the early morning spectacle of a red-eye flight, flying with Southwest is an experience more riveting than a soap opera. It's simply an airborne stage, my dear traveler, on which the marvelous drama of life is enacted.

No one understands the beautiful art of deception better than Southwest with their 'Direct flights'. They effortlessly bob and weave through the skies, making a simple layover appear as though it's the best part of your journey. Some even call it a mini-vacation. You're immersed in a labyrinth of airports, a veritable maze luring you into its depths, only to spit you out, seated in another Southwest aircraft en route to your destination, your final destination. The term "direct” is a delightful euphemism that implies a non-stop journey, when it is anything but. Oh! The sweet irony.

They say that patience is a virtue, and if you’ve ever dealt with last-minute flights, it’s a principle you need to adhere to with a religious fervor. When leaving things to the last-minute, you must offer your prayers up to the 'God of Flight Deals' who may, if you're lucky, bless you with a miracle fare in your time of need. But most often, brace yourself for an uppercut to your wallet that would make Muhammad Ali proud.

To avoid the crushing blow to your finances, you may consider becoming a Frequent Flyer. Yes, ratchet up those miles on Southwest's tantalizing mileage program, where you might engage in a lifelong relationship of adoration and resentment. To the untrained eye, these miles seem to appear faster than a rabid Usain Bolt. And evaporate just as quickly, faster, if possible! Ah, the delicious exaggeration of the mileage program's benefits.

Perhaps the crown jewel of the Southwest experience is the economy class. As ironic as it may sound, the economy class is the epitome of "premium-ness". It's more of a rollercoaster ride through the twilight zone of flying with the added torture of an extra snug seat. With each turbulent jolt, you'll experience an intimate bonding with your co-passenger, an unplanned connection that was never part of your flight itinerary. A small price to pay for the 'luxury' of applying mascara while your elbow competes for dominance with your neighbor over the shared armrest.

The saga of the baggage allowance must not go unmentioned. A game of roulette awaits you at the check-in counter. Will your baggage tip the scales and incur wrath from the airline or will it sneak by unnoticed? This, my friend, is a thrilling conundrum that rivals the mysteries of the universe.

So, sit back and fasten your seatbelts as you embark on this incredible journey with Southwest Airlines. It’s not just a flight, but a fantastical adventure that satirically mirrors the unpredictability and hilarity of life itself. From Dallas to Chicago, reality meets the absurd in the captivating theater of the skies, a spectacle for the traveler who dares to be amused.

Scroll to Top