Take a break from the breeze off Lake Michigan in Chicago. Instead, enjoy the Florida Gulf breeze in Tampa when you fly from Chicago Midway International Airport to Tampa International Airport with Southwest Airlines®. Book with confidence when you fly with Southwest®, no matter if you’re traveling for business, fun, or family. Have flexible travel dates? Search for your Chicago (Midway) flights with our Low Fare Calendar and discover all the ways to save. Explore Southwest Vacations® to find package deals on flights, hotels, rental cars, and more.
Check out Chicago (Midway) to Tampa flights and book yours now!
Average Flight Time: 2 hours 30 minutes
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Tampa International Airport (TPA)
Discover how much more there is to Tampa than its world-renowned beaches. Explore this western Florida city filled with cultural, historical, and natural charm. After you land, getting around Tampa is a breeze—hop on the Hillsborough Area Regional Transit (HART) or Pinellas Suncoast Transit Authority (PSTA) bus, or hail a cab. Explore numerous attractions in downtown Tampa, including the Tampa Museum of Modern Art, a museum that is home to one of the largest Greek and Roman antiquities collections in the southeastern portion of the U.S.
History buffs should check out the American Victory Ship Mariners Museum, a unique attraction containing one of only four operational World War II ships in the U.S. For fans of the outdoors, there’s a pirate-themed water taxi along Tampa’s Riverwalk, Davis Island, and Channel District. Listen to the entertaining historical narration along your tour and get discounts at bars, restaurants, and more with your Pirate Water Taxi wristband. Just outside downtown Tampa is a 16,000-acre wildlife preserve known as Canoe Escape. Immerse yourself in serene natural surroundings and take a self-guided downstream trip on the Hillsborough River.
If you’re a shopper, explore the charm of the gorgeous Hyde Park historical district, full of picturesque tree-lined streets, numerous boutiques, and top national clothing brand brick-and-mortar locations. Sample Tampa’s diverse cuisine, which includes authentic and modern Cuban-style restaurants, waterfront bistros with fresh, succulent seafood, and various bars at which to continue the party into the night.
No matter if you’re traveling to Tampa for business or fun, you’ll find a variety of ways to explore this incredible city and make your trip truly unforgettable. Hop on the next Southwest flight and go explore!
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest Pet Policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
At Southwest, we know that an incredible trip from Chicago (Midway) to Tampa is built with more than cheap flights. We want you to experience a satisfactory flying experience to set the tone for wherever your next adventure may be. That’s why we offer services and perks, from booking to boarding, that make your travel experience as easy and enjoyable as possible. Find out more about the Southwest Experience before you book your Chicago (Midway) to Tampa flight.
It’s simple and fun to fly with Southwest, no matter which of our destinations you choose. And when you search for your next flight to Tampa, you’ll find low fares with no hidden fees. That’s our Transfarency® promise. Enroll in our Click 'N Save® emails and stay in the know about our latest flight deals. Check out the Southwest Travel Guide for extra help planning your trip.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.