Are there nonstop flights from Toronto (YYZ) to Chicago (MDW)?

No. The fastest connection is via Detroit, about 1h 50m of total flying time.

What is the fastest connection from Toronto (YYZ) to Chicago (MDW)?

via Detroit ≈ 1h 50m, via Cleveland ≈ 1h 57m, via Columbus ≈ 2h 7m (estimated flying time, excluding layovers).

Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)・696 km

No nonstop flights. The fastest connection is via Detroit (DTW), about 1h 50m of flying time (layover not included).

None.

15 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.