Fly Southwest: MDW to Roanoke, Virginia
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 Call now to unlock exclusive and unpublished deals.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.
Sophie W.
Booking my flight was a breeze! Seamless process with top-notch customer service. Couldn’t ask for a better experience.
Michael T.
Perfection! Their website is user-friendly and intuitive, made the entire booking process stress-free. Keep it up!
Top tips for flying out of MDW (Chicago) on Southwest Airlines to Roanoke, VA
- Allow more time to sail through security at your undefined start point by making sure that there's nothing in your carry-on luggage to offend TSA standards. As seasoned travelers on this route will know, Southwest airlines have the same security standards as all airlines, but the undefined airport could have unique provisions.
- The Roanoke-Blacksburg Regional Airport, the terminus of our sublime airborne journey, is a smaller airport which means fewer crowds. However, leaving nothing to chance, plan to pick your checked bags from carousel 1 as Southwest flights primarily offload at this point.
- While Southwest allows two checked bags per customer, free of charge, it's always a smart move to pack light. This is particularly useful on flights to Roanoke, considering the airport's petite size can mean somewhat faster baggage processing times.
- With Roanoke's warm summers and chilly winters in mind, pack clothes that suit the season. Long, balmy summer days call for breezy outfits, while the Roanoke winter requires heavier attire.
- Want to make your flight more entertaining? Southwest airlines offer free in-flight entertainment which includes movies, live TV, and custom TV series channels. Use Southwest's mobile app to access these before the trip, perfect for long flights to Roanoke.
- Want to make your flight more entertaining? Southwest airlines offer free in-flight entertainment which includes movies, live TV, and custom TV series channels. Use Southwest's mobile app to access these before the trip, perfect for long flights to Roanoke.
- Given Roanoke's rich history and cultural attractions, pre-booking a rental car from one of the five car rental companies at the airport may be a wise move. Roanoke is a spread-out city and having wheels at your disposal lets you dive straight into exploring.
Things Roanoke, Virginia is Known For
THE BEAUTIFULLY MISERABLE MILL MOUNTAIN STAR
Oh, the highlight of Roanoke. A blazing, neon star relegated to a mountain. Provides a treat for sore eyes...at night, when its intrusive brightness isn't as appalling.
ENDLESS OUTDOORS AT BLUE RIDGE PARKWAY
A mesmerizing 469 miles of scenic roads...because who doesn't love a good, seemingly eternal drive? Perfect for some deep ruminations or plotting world domination.
TAUBMAN MUSEUM OF ART, OUR GLOBAL EXPOSITION
Drown yourself in the awe-inspiringly mundane. Nothing like a hefty dose of artistic snobbery and cultural pretentiousness flying right over your head.
THE ROANOKE STAR CARNIVAL, A UNIQUE AMUSEMENT FEAST
Scream your lungs out on the merry-go-round because nothing drowns existential crisis better than a good old-fashioned glittery fiesta.
CHECK OUT VIRGINIA MUSEUM OF TRANSPORTATION
Bask in the glory of historically important vehicles. Riveting. Be prepared to be fascinated...or not.
THE EXCITING BLACK DOG SALVAGE
Fuel your thirst for salvaged interpretation of art and furniture at Black Dog Salvage. If there's a better way to spend a Saturday...well, there probably is.
FAQs for booking flights from MDW, Chicago to Roanoke, Virginia on Southwest
What are some flight options from Chicago to Roanoke? 

On AirFaresy, we offer a variety of flights from Chicago to Roanoke. You can choose from multiple airlines, including Southwest. Our user-friendly platform makes it easy to compare flight schedules, prices, and layover cities, ensuring you find a flight that best fits your needs.
How do I book a flight on AirFaresy? 

What if I prefer to fly with Southwest? 

Are there special deals or discounts available? 

Can I book a round-trip ticket on AirFaresy? 

What happens if I need to change or cancel my flight? 

What is the baggage policy for my flight from Chicago to Roanoke? 

Flying on Southwest Airlines from MDW (Chicago) to Roanoke, Virginia
Alas, dear traveler, if you're seeking a divine journey with ample legroom and dubious peanuts, allow me to enlighten you on the epic quest from the urban wilderness of undefined Chicago to the enchanted landscapes of Roanoke. Why of course, your chariot awaits you at 'Southwest', where their squawks of 'cheap flights' might allay your wallet's excessive weight.
Indeed, I comprehend the yearning for 'direct flights' – the dread of lingering in transient airport purgatory, your soul shackled to a coffee kiosk, dreading announcements as joyless airport staff inform you that your 'connecting flight' has become a 'non-stop' tour to Sorrowville courtesy of inevitable delays.
But why not explore the realm of the 'layover', my dear friend? A mystical plane where minutes melt into hours, and hours into days whilst you sample the exotic flavors of overpriced sandwiches and riffle through novelty mugs at a glacial pace. Revel in the exhilarating uncertainty! Marvel at the unparalleled joy that sprouts from acquiring essential survival skills like sourcing power outlets and finding tolerable Wi-Fi. Embrace this unexpected detour on your journey from Chicago to Roanoke.
As we delve deeper into the delights of Southwest, it's illuminating to delve upon its generously bare-bones 'Economy Class'. Ah, the resplendent austerity of firm leather and tastefully immovable armrests! Feast your senses on the reusable headphones, capable of translating the latest Hollywood blockbusters into a symphony of crackling static. Marvel at the 'in-flight services', where your call button summons a delightful range of wholly unavailable beverages from a visibly apathetic flight attendant. One might even risk comparing it to 'First-Class' of low-budget regional airlines perfect for those seeking luxury delivered with well-calculated delay.
Now let's take a moment to appreciate the 'flight duration' of this magnificent airborne odyssey. Time, the elusive spectator, renders itself into the Southwest pilot's unwitting accomplice, morphing a casual transcontinental jaunt into a gripping temporal caper. Is your voyage across time zones a mere trick of the clock, or a wrinkle in space-time that mere mortals can't comprehend? Who can tell?
Do you find this journey to Roanoke to be a somewhat last-minute decision? Fear not, for Southwest's 'flight deals' stand as hallowed beacons for procrastinators and spontaneous thrill-seekers alike. These sacred idols of the travel gods are appeased with frequent flyer points, a tithe in your quest for airfare affordability. Thus, your spontaneous sojourn to Roanoke might not be merely a reckless squandering of your savings, but a savvy investment in future thrills.
As we conclude our satirical tour of your impending journey from the rangeless Chicago wilderness to the scenic tranquillity of Roanoke, remember, dear traveler, that the journey is just as memorable as the destination, especially when seasoned with a good pinch of humor. So, strap into your Southwest seat, tighten that loosely buckled seatbelt, and prepare for takeoff into a flight experience bordering the absurdly unforgettable. A whole Southwest world of mild inconvenience and surprise adventures awaits you!