Southwest Airlines
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United States
Midway International Airport
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United States
Southwest Florida International Airport
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Scan through all non-stop flights from Chicago to Fort Myers. The full flight schedule below gives an overview of all non-stop flights from MDW to RSW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Fort Myers is a humid subtropical or warm-temperate destination, featuring hot, humid summers with temperatures typically around 30°C (86°F) and mild to cool winters. The region is known for consistent rainfall throughout the year, peaking in summer. The area is known for its vibrant urban energy, diverse landscapes, and numerous outdoor activities.
You can visit Fort Myers any time of the year, but the best months to explore are from to and from to .
Currently, there is only one airline operating non-stop flights from Chicago MDW to Fort Myers RSW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their MDW RSW flight schedule.
Flights from MDW to RSW are operated 17 times a week, with an average of 2 flights per day. Departure times vary between 05:05 - 19:50. The earliest flight departs at 05:05, the last flight departs at 19:50. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Chicago to Fort Myers takes 2 hours and 45 minutes. The flight distance between Chicago and Fort Myers is 1,106 miles (or 1,780 km).
There is 1 airport in Fort Myers: Southwest Florida International Airport (RSW).
There are 17 flights per week flying from Chicago to Fort Myers (as of April 2026).
2 hours and 45 minutes is the average flight time from Chicago to Fort Myers.
The distance from Chicago to Fort Myers is 1,106 miles (1,780 kilometers).
Southwest Airlines is the only airline flying nonstop from Chicago to Fort Myers.
There are no alliances flying direct from Chicago to Fort Myers at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Fort Myers:
The earliest flight departs at 05:05 from Chicago and arrives at 08:45 at Fort Myers.
The latest flight departs at 19:50 from Chicago and arrives at 23:35 at Fort Myers.
1,106 miles (1,780 km) · 2h 45m
07:25
11:10
Southwest Airlines
WN 1988
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:55
11:40
Southwest Airlines
WN 4301
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
09:00
12:45
Southwest Airlines
WN 1327
Southwest Airlines
Boeing 757
Y
W
J
F
09:15
13:00
Southwest Airlines
WN 1327
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:00
15:45
Southwest Airlines
WN 3466
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:50
16:35
Southwest Airlines
WN 4301
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:00
16:45
Southwest Airlines
WN 4690
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:00
16:45
Southwest Airlines
WN 4690
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:40
19:25
Southwest Airlines
WN 2079
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:05
19:50
Southwest Airlines
WN 2079
Southwest Airlines
Boeing 757
Y
W
J
F
18:55
22:40
Southwest Airlines
WN 2079
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:50
23:35
Southwest Airlines
WN 2079
Southwest Airlines
Boeing 757
Y
W
J
F
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