Are there nonstop flights from Port of Spain (POS) to Chicago (ORD)?

No. The fastest connection is via Sint Maarten, about 6h 11m of total flying time.

What is the fastest connection from Port of Spain (POS) to Chicago (ORD)?

via Sint Maarten ≈ 6h 11m, via Nassau ≈ 6h 14m, via Orlando ≈ 6h 17m (estimated flying time, excluding layovers).

from 23,000 JAL miles, from 30,000 ANA miles (economy, one way, based on the published award charts).

Piarco International Airport (POS) to Chicago O'Hare International Airport (ORD)・4,343 km

No nonstop flights. The fastest connection is via Sint Maarten (SXM), about 6h 11m of flying time (layover not included).

With milesJAL 23,000 miles+ (via MIA)ANA 30,000 miles+ (via EWR)Economy, one way, estimate. Tap a connection for miles by cabin.

None.

11 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.