Are there nonstop flights from Fort Myers (RSW) to Chicago (MDW)?

Yes. Southwest Airlines fly this route. Flight time is about 2h 36m.

What is the fastest connection from Fort Myers (RSW) to Chicago (MDW)?

via Atlanta ≈ 3h 6m, via Louisville ≈ 3h 6m, via Indianapolis ≈ 3h 6m (estimated flying time, excluding layovers).

Southwest Florida International Airport (RSW) to Chicago Midway International Airport (MDW)・1,782 km

Nonstop flights available (1 airline). Flight time about 2h 36m. Nonstop return flights also operate.

41 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

Times are estimated from distance. Check schedules, frequency and availability with the airline or a booking site.