Are there nonstop flights from Chicago (MDW) to Destin (DSI)?

Yes. Southwest Airlines, Allegiant Air fly this route. Flight time is about 2h.

What is the fastest connection from Chicago (MDW) to Destin (DSI)?

via Nashville ≈ 2h 30m, via Indianapolis ≈ 2h 31m, via Louisville ≈ 2h 32m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Destin Executive Airport (DSI)・1,271 km

Nonstop flights available (2 airlines). Flight time about 2h. Nonstop return flights also operate.

27 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.