Are there nonstop flights from San Antonio (SAT) to Chicago (MDW)?

Yes. Southwest Airlines fly this route. Flight time is about 2h 28m.

What is the fastest connection from San Antonio (SAT) to Chicago (MDW)?

via St Louis ≈ 2h 58m, via Dallas ≈ 2h 58m, via Dallas-Fort Worth ≈ 2h 59m (estimated flying time, excluding layovers).

San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW)・1,668 km

Nonstop flights available (1 airline). Flight time about 2h 28m. Nonstop return flights also operate.

32 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.