Fly Southwest: MDW to New York, New York
Get Huge Savings! Call now to unlock exclusive and unpublished deals.
-
Our agents are available 24/7
24/7 SUPPORT
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.
MOST BANG FOR YOUR BUCK!
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.
Jane S.
Fast, efficient online flight booking. Highly recommend. For a tech newbie, I could not have asked for a better experience.
Katie T.
Incredible customer service on the phone, managed my booking changes smoothly. Special shout-out to Jeremy, your kindness won't be forgotten!
Top tips for flying out of MDW (Chicago) on Southwest Airlines to New York, NY
- Navigate through a landscape of logistics with Southwest Airlines, a flight that offers individualized services to optimize your travel experience. From free checked luggage to pre-flight purchases, capitalize on these mechanisms to optimize your journey to New York.
- Journeying to the arresting skyline of New York might expose you to some in-flight turbulence due to weather or air traffic over this busy hub. Southwest Airlines, though, is a master of navigating around such factors, resulting in decreased rates of turbulence-induced disturbances and increased journey comfort.
- Check-in online up to 24 hours prior to your flight to put to good use Southwest's Advanced Boarding process, a flexible mechanism allowing a smoother, calmer pre-flight experience doing away with the mass hustle typically associated with terminal waits.
- The direct flight from undefined to New York on Southwest tends to be packed. Consider an upgrade to a Business Select ticket for guaranteed express boarding and a free premium drink, a minor indulgence to render your journey more comfortable.
- Leverage Southwest's ongoing connectivity collaboration with iHeartRadio, enabling travellers to tune into live radio or curated playlists, a melodic strategy to make your journey to New York more pleasurable.
- Leverage Southwest's ongoing connectivity collaboration with iHeartRadio, enabling travellers to tune into live radio or curated playlists, a melodic strategy to make your journey to New York more pleasurable.
- Tap into Southwest Rapid Rewards® program. Whether it's a Business trip or a Leisure one, rack up points on this trip from undefined to New York, ensuring you gain value over and above the physical journey itself.
Things New York, New York is Known For
EMPIRE STATE BUILDING
A stalwart heart of metal and stone, soaring above the bustling streets, this titanic monument pays tribute to mankind's ceaseless ambition.
STATUE OF LIBERTY
An illuminating beacon of liberty, she stands resolute in the harbor, a silent testament to the enduring allure of freedom and hope.
BROADWAY'S THEATRE DISTRICT
Acres of creative dreams manifested on stages, Broadway reverberates with the echoes of countless applause, a paradise for theatre lovers.
CENTRAL PARK
A verdant, tranquil haven silently pulsing amidst the city's beating heart, Central Park offers an irreplaceable calm within the storm of urban activity.
TIMES SQUARE
Like a rainbow dancing on chrome, Times Square shimmers with a million colors – a vibrant hub of commercial opulence and expressive humanity.
METROPOLITAN MUSEUM OF ART
Enshrining centuries of art and history in its hallowed halls, the Met serves as a timeless vault, safeguarding the world's cultural heritage.
FAQs for booking flights from MDW, Chicago to New York, New York on Southwest
What can I expect when booking my flight from Chicago to New York on AirFaresy? 

AirFaresy is your go-to platform for stress-free and reliable flight booking. We offer a user-friendly interface, which allows you to compare airfares, schedules, and accommodations from various airlines, including Southwest. With our service, you get access to advantageous deals and promotions, ensuring that you receive the best value for your money.
How do I book a flight with AirFaresy? 

I prefer Southwest, but am open to other airlines. How can AirFaresy assist me? 

What safety protocols are in place with airlines during this COVID-19 pandemic? 

What is the next line of action if my flight is cancelled? 

How can I change or cancel my flight once I have booked? 

What type of customer support does AirFaresy offer if I encounter issues? 

Flying on Southwest Airlines from MDW (Chicago) to New York, New York
My friends, I've journeyed across land and through air, traversing vast distances to bring you the story of my latest adventure. Traveling from the heart and soul of our country, "The Windy City" itself, Chicago, to the bustling and never-sleeping skyline of New York. I have held an experience that is nothing short of sublime, and one that I flew on the wings of Southwest Airlines, feeling utmost comfort and topnotch customer service, ensuring my journey was nothing short than extraordinary.
I embarked on what may be viewed by some as a daunting and tedious task. Yes, folks, the formidable challenge of booking flights! And not just any flight, but the pursuit of cheap flights that give you the most for your money's worth but, without compromising on the quality. But let me tell you, Southwest Airlines made it as easy as it can be, putting out some of the most competitive and affordable airfare for their loyal patrons.
I have always found round-trip journeys to be the most economical and convenient choice. But on Southwest Airlines, the freedom to choose between round-trip and one-way tickets is a boon for all those spontaneous travelers who love to remain unplanned and unpredictable! And I assure you, one-way or round trip, I enjoyed every minute in Southwest's economy class, delivering comfort and affordability combined into an irresistible package.
We are all aware of the dread that a troublesome layover brings. The fear of missed connecting flights, the stress of rushing through unfamiliar airports. The beauty of Southwest's flight schedule is the provision for non-stop, direct flights from Chicago to New York. The ease and comfort of these flights are unmatched, my friends, and you experience the journey in a smooth, unbroken fashion. Now, isn't that a blessing?
Attention must be given to the impressive in-flight services that Southwest offers. From friendly cabin staff to a comfortable environment, Southwest pays keen attention to making your flight duration worthwhile. Their baggage allowance policy is also quite generous, accommodating those extra souvenirs and shopping bags you ended up buying last minute without any hassle!
You might be wondering—how can service be this good? Don't just take my word for it, my dear readers. There are countless airline reviews in praise of Southwest's exemplary customer service, uncompromised safety, and impressive punctuality. Their commitment towards passengers shines through every encounter, every service.
Keep a keen eye out for Southwest's flight deals, appearing regularly throughout the year. Even the most last-minute flights can be surprisingly light on the pocket on Southwest. And for all you frequent flyers out there, let me let you in on a little secret: Southwest's admirable mileage program, rewarding loyalty and consistent flight usage with enticing benefits.
In conclusion, be it direct flights or one-way trips, business or leisure travels, for an experience that wraps you in comfort without causing a dent on your pocket, Southwest Airlines is the avenue to explore. So next time you plan your trip, think no further than Southwest Airlines, friends, and soar through the clouds in an unforgettable journey from Chicago to New York.