Fly Southwest: BOS to Chicago, Illinois
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Lori H.
So simple and stress-free! Booked my flight online in a jiff, perfect for those not so tech-savvy like myself.
Ralph V.
Impressive customer service over phone. The representative was patient and insightful, helped reschedule my flight last minute.
Top tips for flying out of BOS (Boston) on Southwest Airlines to Chicago, IL
- Southwest’s open seating policy may make you anxious if you prefer an aisle or window seat. To get your preferred seat without stress, it's wise to consider paying the small extra fee for Southwest's EarlyBird Check-In. This automatically checks you in 36 hours before your flight, allowing you to board earlier and thus having the pick of the seats.
- When flying from an unknown airport to Chicago via Southwest, ensure to have a layover plan ready. Depending on your originating airport, there might be more than one stopover. Prepare for the possibility of a layover by packing a good book or ensuring your devices are charged to keep you entertained.
- Although Southwest doesn't offer in-flight meals, it does provide complimentary drinks and snacks. However, as you'll be on a lengthy journey to Chicago you may want to carry some packed food. It's always better to have something to fall back on, particularly if you have diet restrictions.
- Southwest Airlines is unique in allowing two checked bags for free. Don't leave that benefit on the table since other airlines typically charge hefty fees for luggage. As a traveller flocking to Chicago; embrace Southwest's generous baggage policy and don't fret about the added cost you'd otherwise encounter on another flight.
- Midway International Airport, one of Southwest's hubs, is a smaller airport than the famed O'Hare, yet it is conveniently located closer to downtown Chicago. Do not be alarmed when your flight lands here, it may actually work in your favor for transport into the city.
- Midway International Airport, one of Southwest's hubs, is a smaller airport than the famed O'Hare, yet it is conveniently located closer to downtown Chicago. Do not be alarmed when your flight lands here, it may actually work in your favor for transport into the city.
- Southwest Airlines generally have high on-time rates, but delays do happen. Sign up for flight status alerts and make use of the Southwest mobile app for real time updates. This way, you will have accurate notifications should any delay or time adjustments occur.
Things Chicago, Illinois is Known For
THE EMBRACING ARMS OF LAKE MICHIGAN
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.
THE INTERLACING THREADS OF CHICAGO'S MUSIC SCENE
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 LYRICAL NARRATION OF THE ART INSTITUTE OF CHICAGO
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 GOTHIC OSPREY OF THE CHICAGO TRIBUNE TOWER
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 RHYTHMIC POUNDING OF THE CHICAGO MARATHON
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.
THE JOVIAL DANCE OF CHICAGO PIZZA
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 BOS, Boston to Chicago, Illinois on Southwest
What makes AirFaresy the ideal platform for booking my flight from Boston to Chicago? 
AirFaresy stands as the paragon of simplicity, transparency, and efficiency in the crowded landscape of flight booking services. We've meticulously developed a platform that demystifies the process of navigating through airline options and finding the best value. Our algorithms rapidly scan and compare prices from different airlines, including Southwest, to offer you nothing less than the best. Whether you choose to use our user-friendly online platform or speak with our knowledgeable customer service representatives over the phone, AirFaresy is dedicated to making your flight booking experience hassle-free.
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Flying on Southwest Airlines from BOS (Boston) to Chicago, Illinois
Oh, propitious day! You've chosen to fly from the commanding metropolis of Boston to the majestic plains of Chicago. And even better, you've elected to do it with the veritable paragon of aviation, Southwest. Well, aren't you just a genius. Clearly, you sought no less than celestial guidance in making such a sanctified selection.
After all, not all flights are created equal. Some, like the direct flights offered by our dearest Southwest, prefer not to meander around the country, high on jet fuels and ludicrous detours. No, sir! They'd much rather dash straight to their destined cities, curveballs and layovers be damned. Of course, because nothing screams vacation than being cooped up in a plane for longer than is necessary, right?
But pray, pay these irrelevant layovers no mind. Because by divine intervention, you're blessed with non-stop service, courtesy again of your esteemed choice of airline. Yes, non-stop - as in, the plane won't suddenly decide to stop mid-air for a coffee break. Or, heaven forbid, force you into bewildering aero-mazes known as airports for connecting flights. Quite the innovation, I must say.
And bless your wallet-friendly heart, you probably think Southwest offers cheap flights. Well then, how laudable, your fiscal prudence. One can only applaud the thought of sardining oneself in a tight metal tube with a hundred strangers for hours, all in the name of penny-pinching.
Let's not forget to commend this unsuspecting little nugget of miracle they call the red-eye flight, another gift bestowed upon us by our dear aviation industry. It allows us to enjoy sleep deprivation at unheard-of altitudes—because nothing primes you for arrival in a new city like dark circles under the eyes and an overwhelming urge to snooze.
So there you have it, cautious traveler. A charming ride awaits you, packed with gales of laughter and pinpricks of sarcasm. Fly Southwest from Boston to Chicago, and walk away with stories enough to last several lifetimes—metaphorical lifetimes, perhaps, but who's keeping track?
One last advice though—brace for the unexpected. Perhaps a rhyming flight attendant or a potato-sack race down the aisle. After all, you're flying Southwest, where the unexpected is just another layer of 'fun'. Safe travels!
