Are there nonstop flights from Chicago (MDW) to Calgary (YYC)?

No. The fastest connection is via Minneapolis, about 3h 39m of total flying time.

What is the fastest connection from Chicago (MDW) to Calgary (YYC)?

via Minneapolis ≈ 3h 39m, via Denver ≈ 4h 23m, via Detroit ≈ 4h 24m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Calgary International Airport (YYC)・2,247 km

No nonstop flights. The fastest connection is via Minneapolis (MSP), about 3h 39m of flying time (layover not included).

None.

21 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.