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 Fort 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 Fort Myers/Naples flights and book your upcoming trip now!
Chicago (Midway), IL to Fort Myers/Naples, FL
departing on 12/15
one-way starting at*$141
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available.
|Departing from||Chicago Midway International Airport (MDW)|
|Arriving at||Southwest Florida International Airport (RSW)|
|Average flight time||2 hours 46 minutes|
|3‡||Nonstop flights per day Monday through Friday|
|5‡||Nonstop flights on Saturday|
|3‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022.
Known as a gateway for Southwest Florida, Fort 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, Fort Myers is a top destination for tourists, and it's easy to see why.
When you travel to Fort 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 Fort 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.
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 Fort 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 Fort 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 Fort 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. 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.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.