Nonstop flights from Fort Myers to Chicago

Southwest Airlines flies this route 2 to 3 times a day.

RSWFort Myers Southwest Florida International

1,107 mi · 17 flights a week

MDWChicago Midway International

RSWMDW

When they leave

Fort Myers time

6:50a5:40pFirst departure 6:50 AM, last 5:40 PM

Three in the morning, 6:50 AM to 11:55 AM, then two in the evening, 5:25 PM to 5:40 PM.

Every flight

Earliest first

6:50 AM→8:40 AMSouthwest AirlinesBoeing 737Mon, Thu, Fri
7:10 AM→8:55 AMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat, Sun
11:55 AM→1:45 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
5:25 PM→7:15 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
5:40 PM→7:30 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat, Sun

Schedules last checked Sep 21, 2026. Times are local.

Flying from Fort Myers to Chicago

Southwest Airlines is the only airline flying nonstop from Fort Myers to Chicago, 2 to 3 times a day on the Boeing 737 MAX 8 and Boeing 737.

Flights run every day of the week, 3 on Mondays, Thursdays and Fridays and 2 on the other days. The first arrival in Chicago is at 8:40 AM and the last at 7:30 PM. The flight covers 1,107 miles.

Flying back, Chicago to Fort Myers has 17 nonstop flights a week. From Fort Myers, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 42 a week.