Nonstop flights from Chicago to Fort Myers
3 airlines fly from 2 Chicago airports (MDW and ORD) to Fort Myers (RSW), with up to 9 flights a day.
Routes
2 airport pairs- MDW to RSWChicago Midway to Southwest Florida2 to 3 a day
- ORD to RSWChicago O'Hare to Southwest Florida7 a week
When they leave
Chicago timeFive in the morning, 7:00 AM to 10:51 AM, then four in the afternoon, 12:15 PM to 4:30 PM, then three in the evening, 6:00 PM to 6:50 PM.
Every flight
Earliest first
Schedules last checked Sep 27, 2026. Times are local.
Flying from Chicago to Fort Myers
Southwest Airlines flies most often, 2 to 3 times a day on the Boeing 737 MAX 8 and Boeing 737. United Airlines flies 4 times a week on the Boeing 737 MAX 9, Airbus A321neo and Boeing 737. American Airlines flies 3 times a week on the Airbus A321, Boeing 737 and Boeing 737 MAX 8.
Flights run every day of the week, from 2 on Tuesdays, Wednesdays and Saturdays to 9 on Sundays. The first arrival in Fort Myers is at 10:58 AM and the last at 10:52 PM.
MDW to RSW is the busiest airport pair, with 17 flights a week, then ORD to RSW with 7.
Flying back, Fort Myers to Chicago has 59 nonstop flights a week.
Return flights
Find the cheapest day to fly from Chicago to Fort Myers.
Schedules as of Oct 9, 2026.