Are there nonstop flights from Tampa (TPA) to Chicago (MDW)?

Yes. Southwest Airlines fly this route. Flight time is about 2h 23m.

What is the fastest connection from Tampa (TPA) to Chicago (MDW)?

via Atlanta ≈ 2h 53m, via Indianapolis ≈ 2h 53m, via Louisville ≈ 2h 54m (estimated flying time, excluding layovers).

Tampa International Airport (TPA) to Chicago Midway International Airport (MDW)・1,607 km

Nonstop flights available (1 airline). Flight time about 2h 23m. Nonstop return flights also operate.

48 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.