Southwest® flights from Chicago-Midway to Fort Myers/Naples from $149
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Low fares from Chicago-Midway to Fort Myers/Naples
$
Chicago-Midway (MDW)to
Fort Myers/Naples (RSW)
Depart: 12/17/2026
One-way
Basic
From
$149
Seen: 13 hrs ago
Chicago-Midway (MDW)to
Fort Myers/Naples (RSW)
Depart: 12/02/2026
One-way
Basic
From
$149
Seen: 15 hrs ago
Chicago-Midway (MDW)to
Fort Myers/Naples (RSW)
Depart: 12/05/2026
One-way
Basic
From
$149
Seen: 19 hrs ago
Chicago-Midway (MDW)to
Fort Myers/Naples (RSW)
Depart: 11/09/2026
One-way
Basic
From
$149
Seen: 7 hrs ago
Chicago-Midway (MDW)to
Fort Myers/Naples (RSW)
Depart: 10/28/2026
One-way
Basic
From
$149
Seen: 6 hrs ago
Chicago-Midway (MDW)to
Fort Myers/Naples (RSW)
Depart: 12/12/2026
One-way
Basic
From
$149
Seen: 3 hrs ago
Explore flights from Chicago-Midway to Fort Myers/Naples
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Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
Southwest Florida Regional Airport
Average flight time:
2 hours 40 minutes
Distance:
1105 miles
Route Information
147† Weekly flights
- 2‡ Nonstop flights per day Monday through Friday
- 3‡ Nonstop flights on Saturday
- 3‡ Nonstop flights on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Fort Myers/Naples
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.
Questions we hear the most
The average flight time from Chicago (Midway) to Fort Myers/Naples is 2 hours 40 minutes.
There are 147 weekly flights from Chicago (Midway) to Fort Myers/Naples on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to Fort Myers/Naples 2 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to Fort Myers/Naples 3 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to Fort Myers/Naples with Southwest, check out our Low Fare Calendar.
You can rent a car at Southwest Florida Regional Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to Fort 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.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
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