Flights from Chicago (MDW) to Ft. Myers/Naples (RSW)

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!

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Chicago (Midway), IL to Ft. Myers/Naples, FL

departing on 12/17

one-way starting at*

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*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 29 travel days available.

Check out Chicago (Midway) to Ft. Myers/Naples flights and book yours now!

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Travel Advisory

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 Coronavirus Travel Information page for information about potential restrictions on air travel.

Flight details

Average flight time: 2 hours 47 minutes

Departing from: Chicago Midway International Airport (MDW)

Arriving at: Southwest Florida International Airport (RSW)


Route information


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Based on DOT published scheduled average flights Monday-Friday between 10/30/2020 and 12/31/2020, as of 11/2/2020.

Explore Ft. Myers/Naples

Known 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!

Travel tips


Infancy policy

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.


Pet policy

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.


Unaccompanied minor

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.


Bags fly free®1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.


The Southwest travel experience

At Southwest, we know that a lot goes into planning the perfect trip from Chicago to Ft. Myers, and it means more than getting a great, cheap flight from Midway to Southwest Florida International Airport. That's why we offer services and perks, from booking to boarding, that make your travel experience as simple and fun as possible. Find out more about the Southwest® Experience before you book your next flight to Ft. Myers/Naples from Chicago (Midway).

Booking is simple with Southwest, no matter which of our dozens of exciting destinations you choose to visit. And when you search for your next flight to Ft. Myers/Naples, you'll score 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 and other opportunities to save. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.

Questions we hear the most

How long is the flight from Chicago (Midway) to Ft. Myers/Naples?

The average flight time from Chicago (Midway) to Ft. Myers/Naples is 2 hours 47 minutes.

How many Southwest flights from Chicago (Midway) to Ft. Myers/Naples occur daily?

There are 14 flights daily from Chicago (Midway) to Ft. Myers/Naples on Southwest Airlines.

Does Southwest fly nonstop from Chicago (Midway) to Ft. Myers/Naples?

Southwest flies nonstop from Chicago (Midway) to Ft. Myers/Naples 4 times daily.

What day is it cheapest to fly from Chicago (Midway) to Ft. Myers/Naples?

To find the cheapest day and time to fly Chicago (Midway) to Ft. Myers/Naples with Southwest, check out our Low Fare Calendar.

Can I rent a car at Southwest Florida International Airport?

You can rent a car at Southwest Florida International Airport—book yours with your flight.

Can I change my flight reservation for my flight from Chicago (Midway) to Ft. Myers/Naples?

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.

Where can I find the status of my flight from Chicago (Midway) to Ft. Myers/Naples?

Check the status of your upcoming Southwest flight here.

Where can I find answers to other questions about flying from Chicago (Midway) to Ft. Myers/Naples with Southwest?

Check out the Southwest Airlines® FAQs for answers about everything Southwest.