Are there nonstop flights from Sydney (SYD) to Chicago (MDW)?

No. The fastest connection is via Los Angeles, about 18h 29m of total flying time.

What is the fastest connection from Sydney (SYD) to Chicago (MDW)?

via Los Angeles ≈ 18h 29m, via San Francisco ≈ 18h 34m, via Dallas-Fort Worth ≈ 18h 46m (estimated flying time, excluding layovers).

Sydney Kingsford Smith International Airport (SYD) to Chicago Midway International Airport (MDW)・14,871 km

No nonstop flights. The fastest connection is via Los Angeles (LAX), about 18h 29m of flying time (layover not included).

None.

4 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.