Are there nonstop flights from Chicago (MDW) to Charlotte Amalie (STT)?

No. The fastest connection is via Charlotte, about 4h 59m of total flying time.

What is the fastest connection from Chicago (MDW) to Charlotte Amalie (STT)?

via Charlotte ≈ 4h 59m, via San Juan ≈ 5h 2m, via Atlanta ≈ 5h 9m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Cyril E. King Airport (STT)・3,384 km

No nonstop flights. The fastest connection is via Charlotte (CLT), about 4h 59m of flying time (layover not included).

None.

12 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.