Direct flights from Fort Myers to Chicago

  • ~2 flights a day
  • Southwest Airlines

🔔 Track this route

We check RSW → MDW every day and email you the cheapest nonstop fares we find.

Free · one-click unsubscribe

When the nonstops leave

Typical weekly schedule · 15 flights per week (~2 per day) · Updated 79d ago

Most leave in the morning.

Morning before noon 12 a week

Arrive the same day

5:10 AMMon, Thu, Fri 7:10 AMTue, Wed 7:20 AMSun 11:40 AMnot Sun
Afternoon noon – 6 PM 2 a week

Arrive the same day

2:55 PMSat 5:10 PMSun
Evening after 6 PM 1 a week

Arrive the same day

6:00 PMSat
Southwest Airlines

More nonstops from Fort Myers

RSW → EWR Newark 2 airlines RSW → BWI Baltimore RSW → PVD Providence/Warwick 3 airlines RSW → BNA Nashville RSW → IND Indianapolis RSW → MCO Orlando RSW → STL St Louis RSW → HVN New Haven 2 airlines MDW → RSW The return trip RSW All nonstops from Fort Myers MDW All nonstops from Chicago

Frequently asked questions

Is there a direct flight from Fort Myers to Chicago?

Yes. Southwest Airlines flies nonstop from Fort Myers (RSW) to Chicago (MDW), daily. The flight takes about 2h 47m and covers 1,107 miles (1,782 km). Schedule data from 31 July 2026.

Which airlines fly direct from Fort Myers to Chicago?

Southwest Airlines operates nonstop flights from Fort Myers to Chicago.

How long is the flight from Fort Myers to Chicago?

The nonstop flight from Fort Myers to Chicago takes ~2h 47m (approximately 1782 km).

How often do direct flights operate from Fort Myers to Chicago?

Nonstop flights from Fort Myers to Chicago operate daily — 15 flights per week (~2 per day).

What days of the week are there direct flights from Fort Myers to Chicago?

Direct flights from Fort Myers to Chicago operate every day of the week.