Are there nonstop flights from Washington (DCA) to Chicago (MDW)?

Yes. Southwest Airlines fly this route. Flight time is about 1h 38m.

What is the fastest connection from Washington (DCA) to Chicago (MDW)?

via Columbus ≈ 2h 9m, via Pittsburgh ≈ 2h 9m, via Cleveland ≈ 2h 10m (estimated flying time, excluding layovers).

Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)・964 km

Nonstop flights available (1 airline). Flight time about 1h 38m. Nonstop return flights also operate.

38 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.