Travel from the City of the Big Shoulders to the City of Palms on Southwest Airlines® and trade the beaches of Lake Michigan for the beautiful, sunny beaches along the Gulf of Mexico. Southwest® has flights from Chicago Midway International Airport to Southwest Florida International Airport that will make booking your trip a walk on the beach. Find flights from Chicago (Midway) to Ft. Myers/Naples with Southwest® and book with confidence, knowing your travel will be simple and fun. If your upcoming trip has flexible dates, search for flights with our Low Fare Calendar and discover the lowest fares we have. Don't forget to explore Southwest Vacations® to find deals on flights, hotels, rental cars, and other great packages.
Your bags are ready to be packed. Check out Chicago (Midway) to Ft. Myers/Naples flights and book your upcoming trip now!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Chicago (Midway), IL to Ft. Myers/Naples, FL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 15 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Southwest Florida International Airport (RSW)
Other popular flights from Chicago (Midway)
View our interactive mapKnown as a gateway for Southwest Florida, Ft. Myers is just a 20-minute drive northwest from Southwest Florida International Airport. Famed for its golf courses, deep-sea fishing, and exquisite white sand beaches, Ft. Myers is a top destination for tourists, and it's easy to see why.
When you travel to Ft. Myers, you can delve into the minds and accomplishments of two titans of American industry: Inventor Thomas Edison and automaker Henry Ford. The estates of both iconic innovators and have been transformed into 20 acres of historical buildings, botanical gardens, research laboratories, and museum exhibits. Get a little history lesson in between trips to the beach.
Located less than an hour's drive south of Ft. Myers is the picturesque city of Naples, one of the wealthiest cities in America. Explore luxury shopping at chic boutiques and art galleries, or go in for high-end dining at beachfront bars and restaurants. There's something to satisfy whatever you're craving. Nature lovers can also check out the nearby Everglades and the NGALA Wildlife Preserve where they can get up close and personal with incredible exotic animals like white rhinos, giraffes, zebras, and more!
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.
Deplane at Southwest Florida International airport and start your fun-in-the-sun Florida excursion.
At Southwest, we know it takes more than great deals on Ft. Myers/Naples airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to Ft. Myers/Naples the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to Southwest Florida International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Ft. Myers/Naples, know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Looking for tours, activities, and more hidden gems to add to your Ft. Myers/Naples adventure? Explore getaways with Southwest®. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
To find the cheapest day and time to fly Chicago (Midway) to Ft. Myers/Naples with Southwest, check out our Low Fare Calendar.
You can rent a car at Southwest Florida International Airport—book yours with your flight.
Yes! Flights from Chicago (Midway) to Ft. Myers/Naples—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight here.
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
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