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Allegiant Airline Flights from Chicago to St. Pete-Clearwater International Airport

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Fly Southwest: MDW to Clearwater, Florida

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Allegiant Airline Flights from Chicago to St. Pete-Clearwater International Airport

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Allegiant Airline Flights from Chicago to St. Pete-Clearwater International Airport

Henry T.

Priceless service! Booking was made effortlessly online. Recommend to any travelling savant!

Allegiant Airline Flights from Chicago to St. Pete-Clearwater International Airport

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Phoned in to book a last-minute flight. Beyond impressed with the kindness and efficiency from the staff.​

Top tips for flying out of MDW (Chicago) on Southwest Airlines to Clearwater, FL

 Things Clearwater, Florida is Known For

CLEARWATER BEACH

Clearwater Beach, dubbed the 'Best Beach in America', sparks joy with its white sand and glistening waters. It's loved by sun-seekers looking for peace and serenity, or adventure and watersports.

PIER 60

Pier 60, a pillar of Clearwater's soul, hosts the daily 'Sunsets at Pier 60' festival. This burst of energy and color, with crafts, music, and street performers, stirs feelings of community spirit.

CLEARWATER MARINE AQUARIUM

Hope resonates from the Clearwater Marine Aquarium's inspiring commitment to rescue, rehabilitate, and release marine life. Stars of Dolphin Tale, Winter and Hope, continue to touch hearts worldwide.

RUTH ECKERD HALL

Known for electrifying performances, the Ruth Eckerd Hall stirs audience emotions in its acoustically perfect setting. From rock concerts to Broadway shows, it moves and invigorates arts enthusiasts.

CLEVELAND STREET DISTRICT

Cleveland Street District thrives as Clearwater’s arts, culture, and food scene. Its vibrant energy, coupled with a historic allure, evokes strong local pride and visitor fascination.

CAPITOL THEATRE

The historic Capitol Theatre, with its vintage charm and rich schedule of events, captivates the hearts of music lovers and film buffs, making it an icon of Clearwater's cultural landscape.

FAQs for booking flights from MDW, Chicago to Clearwater, Florida on Southwest

What's the best time to book my flight from Chicago to Clearwater on Southwest?

Hey, mate! If you're after the best deals for Southwest flights from Chicago to Clearwater, it's usually best to book your tickets about two months in advance. Remember, prices fluctuate due to demand, so make sure to check AirFaresy regularly or set up an alert. We'll help you stay updated!

I have a tight schedule. Does Southwest offer non-stop flights from Chicago to Clearwater?

Absolutely! Time is gold, right? Southwest offers direct flights from Chicago to Clearwater, so you don't have to worry about layovers. Just type in the details on our search bar at AirFaresy, and we’ll show you all the available options.

Can I modify or cancel my booking if my plans change?

Change of plans happens to all of us! At AirFaresy, we understand that. Many Southwest tickets can be modified without penalty. However, it is always best to check the fare conditions before you book. Our team at AirFaresy will gladly help you with modifications or cancellations. After all, your peace of mind is what matters to us!

Is it cheaper to book a round trip or two one-way tickets on Southwest from Chicago to Clearwater?

Hey, good question! Prices vary based on factors like availability, time, and demand. Sometimes it's cheaper to book a round trip, sometimes two one-ways. To make sure you snag the best deal, use our AirFaresy comparison tool. Whether it's a round trip or two one-ways, we got your back!

I need to fly Southwest. Can AirFaresy help me find accommodation in Clearwater too?

You bet! AirFaresy is not just about booking flights. We also offer hotel bookings in Clearwater and anywhere else you travel to. So you can relax, knowing that we've got your entire trip covered. Pack your bags, adventure awaits!

What amenities can I expect on my Southwest flight from Chicago to Clearwater?

Southwest ensures a comfortable journey for its passengers. They offer in-flight entertainment, snacks, beverages, and Wi-Fi - though some services may come at an extra cost. For more specifics, reach out to our knowledgeable AirFaresy team. We can help you get the detailed scoop!

How soon should I reach the airport for my Southwest flight from Chicago to Clearwater?

Typically, it's advised to reach the airport at least 2 hours prior to your domestic flight departure. This leaves you enough time for check-in, security checks, and relaxing a bit before your flight. Remember, at AirFaresy, we're always ready to help you plan your journey with ease. Happy travels!

Flying on Southwest Airlines from MDW (Chicago) to Clearwater, Florida

Caressed by the cool winds of Lake Michigan, set at jet's belly when it roars to life, you stand, heeding the calling of the southwest of circumstances undefined. Cradled in the bustle of Chicago's busy streets, a sense of adventure ignites within you, pitch and fervor of anticipation echoing through your veins as 'flight,' the word, takes on glorious forms in your mind. Southwest: your steel-winged chariot, waits, ready to conquer the cerulean infinity.

Book is a misnomer. It is a christening of dreams, of one-way ventures into novel horizons and round-trip dalliances with excitement. It is not a mere pressing of internet keys but a profusion of sweetly intoxicating decisions. For with each trip, a part of you alters, reshapes into someone returned but never quite the same. Always remember the best time to book is when your heart whispers "now," veiling in delight the hows and the whys of cheaper flights or airfare statistics.

The flight duration recedes when you engage with the romance of travel. For aren't you setting off to become a celestial wayfarer, but for a while? When flying Southwest, it is the layover that beautifully punctuates the prose of your journey. The period of waiting begins to bristle with emotion, with a collective sigh of the venture momentarily halted like a parley between destinations.

Souls buoyed by wanderlust are never just 'passengers.' For you recline in more than just a 'budget economy class,' you become the fulcrum and the tale. Amid the cloud-strewn theatre and the drone of engines, Southwest unfurls in-flight services, but it does more than serve meals and soft melodies to lull you to rest. It nurtures and nourishes the stories within you, raw and unsorted yet brimming with potential, like diamonds in their darkest mantle.

In the grand epic of your journey, seldom foreseen, are chapters of alteration and delay. Reflect upon the flight cancellation policy with grace. For isn’t life, as it is with travels, poised delicately between spontaneity and design, unraveling itself in poetry both composed and unrehearsed? Be it last-minute flights or soaring with the red-eye up above, view each veer and flutter with philosophic acceptance.

The beauty with Southwest isn't merely in that it connects Chicago to Clearwater. It delicately threads together the spirit of two cities separated by three states and the waltz of longitudes, yet united in their enchantment for the wanderer in you. You do not merely leap into connecting flights. You tenderly knit together chapters of your travels, slip seamlessly from verse to verse in your odyssey's Psalms.

The journey arrives in its own time, and yet, in all this emotive clamor of flight and landing, remember to treat the baggage allowance like a trusted companion. Bear lightly what needs to be relegated to the belly of the plane, wear tenderly what brings joy when at your fingertips. Possessions can but accompany; your true carry-on in these cloud-climbing pursuits is the spirit of being.

Prepare to sever ties with the city of winds, cast your sights on sunny Clearwater. Surrender yourself to continue onward, to slide, unresisted, into the comforting embrace of the west wind. Southwest awaits - in it, cradle your flights of fancy, allow it to uplift you and carry you toward realms unseen.

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