Are there nonstop flights from Chicago (MDW) to Santiago (STI)?

No. The fastest connection is via Orlando, about 4h 37m of total flying time.

What is the fastest connection from Chicago (MDW) to Santiago (STI)?

via Orlando ≈ 4h 37m, via Fort Lauderdale ≈ 4h 40m, via Miami ≈ 4h 40m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Cibao International Airport (STI)・2,968 km

No nonstop flights. The fastest connection is via Orlando (MCO), about 4h 37m of flying time (layover not included).

None.

7 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.