Are there nonstop flights from Chicago (MDW) to Santa Cruz (VVI)?

No. The fastest connection is via Miami, about 9h 19m of total flying time.

What is the fastest connection from Chicago (MDW) to Santa Cruz (VVI)?

via Miami ≈ 9h 19m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Viru Viru International Airport (VVI)・7,077 km

No nonstop flights. The fastest connection is via Miami (MIA), about 9h 19m 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.