Are there nonstop flights from Sitka (SIT) to Chicago (MDW)?

No. The fastest connection is via Seattle, about 5h 54m of total flying time.

What is the fastest connection from Sitka (SIT) to Chicago (MDW)?

via Seattle ≈ 5h 54m (estimated flying time, excluding layovers).

Sitka Rocky Gutierrez Airport (SIT) to Chicago Midway International Airport (MDW)・3,740 km

No nonstop flights. The fastest connection is via Seattle (SEA), about 5h 54m of flying time (layover not included).

None.

1 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.