Nonstop flights from Chicago to Fort Myers

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

MDWChicago Midway International

1,107 mi · 17 flights a week

RSWFort Myers Southwest Florida International

MDWRSW

When they leave

Chicago time

8:50a6:15pFirst departure 8:50 AM, last 6:15 PM

Two in the morning, 8:50 AM to 9:00 AM, then two in the afternoon, 1:00 PM to 3:05 PM, then two in the evening, 6:00 PM to 6:15 PM.

Every flight

Earliest first

8:50 AM→12:40 PMSouthwest AirlinesBoeing 737Tue, Wed, Sat
9:00 AM→12:45 PMSouthwest AirlinesBoeing 737Mon, Thu, Fri, Sun
1:00 PM→4:45 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
3:05 PM→6:50 PMSouthwest AirlinesBoeing 737 MAX 8Sat
6:00 PM→9:45 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sun
6:15 PM→10:00 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri

Schedules last checked Sep 19, 2026. Times are local.

Flying from Chicago to Fort Myers

Southwest Airlines is the only airline flying nonstop from Chicago to Fort Myers, 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 Fort Myers is at 12:40 PM and the last at 10:00 PM. The flight covers 1,107 miles.

Flying back, Fort Myers to Chicago has 17 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Fort Myers, 7 a week.

Return flights

Fort Myers to ChicagoView

Every Chicago airport

All Chicago to Fort Myers flightsView

Find the cheapest day to fly from Chicago to Fort Myers.

Schedules as of Oct 9, 2026.