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

No. The fastest connection is via Columbus, about 2h 6m of total flying time.

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

via Columbus ≈ 2h 6m, via Pittsburgh ≈ 2h 7m, via Cleveland ≈ 2h 8m (estimated flying time, excluding layovers).

Washington Dulles International Airport (IAD) to Chicago Midway International Airport (MDW)・927 km

No nonstop flights. The fastest connection is via Columbus (CMH), about 2h 6m of flying time (layover not included).

None.

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.