Are there nonstop flights from Osaka (KIX) to Chicago (MDW)?

No. The fastest connection is via San Francisco, about 14h 44m of total flying time.

What is the fastest connection from Osaka (KIX) to Chicago (MDW)?

via San Francisco ≈ 14h 44m, via Los Angeles ≈ 15h 9m (estimated flying time, excluding layovers).

Kansai International Airport (KIX) to Chicago Midway International Airport (MDW)・10,474 km

No nonstop flights. The fastest connection is via San Francisco (SFO), about 14h 44m of flying time (layover not included).

None.

2 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.