Chicago to Port of Spain (ORD–POS) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
While no nonstop service exists between ORD and POS, 1-stop connecting options are available.
Connection Landscape
On-Time Performance
Travel Essentials
ORD: CDT · POS: AST
When it's 6:00 PM in Chicago, it's 7:00 PM in Port of Spain.
US passport holders enter Trinidad and Tobago visa-free for up to 90 days. No advance application is needed. Passport must be valid for the duration of the stay. A return or onward ticket and proof of accommodation are required. At Piarco International Airport (POS) in Trinidad or A.N.R. Robinson International Airport (TAB) in Tobago, immigration stamps your passport.
Trinidad and Tobago is a twin-island republic 11km off the coast of Venezuela. Trinidad is the larger, more urbanized island: Port of Spain hosts Carnival (the Monday and Tuesday before Ash Wednesday), one of the Caribbean's biggest street festivals. Tobago is quieter, with reef diving at Speyside, the oldest protected rainforest in the Western Hemisphere (Main Ridge Forest Reserve, established 1776), and beaches at Pigeon Point and Englishman's Bay. Caribbean Airlines operates the inter-island "air bridge" between POS and TAB (20 minutes, about 15 flights per day).
Direct flights from Miami (MIA) to Port of Spain run about 3 hours 30 minutes on American Airlines and Caribbean Airlines. New York JFK to POS runs about 5 hours on JetBlue and Caribbean Airlines. Fort Lauderdale and Houston also have nonstop service. Trinidad and Tobago uses the Trinidad and Tobago dollar (TTD), trading at roughly 6.80 TTD per $1. US dollars are accepted at hotels and tourist businesses. ATMs are common. Card payments work at restaurants and shops. Maxi-taxis (minibuses color-coded by route) are the main public transport at TTD 4 to TTD 8 per ride. Water taxis connect Port of Spain to San Fernando (1 hour, TTD 15) along the western coast of Trinidad.
CTA Blue Line runs 24/7 from downtown Loop stations to O'Hare (45 min, $5). Pace buses serve suburbs. Ride-shares cost $35–55 from downtown depending on traffic; add 30+ minutes during rush hour on the Kennedy Expressway.Economy parking lots E/F connect via ATS people mover. Terminal 5 (international) is separate from Terminals 1–3; allow extra time for inter-terminal transfers.
ORD–POS Quick Facts
Frequently Asked Questions
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Orlando, Miami and Fort Lauderdale Hollywood. Two-stop connections are also available via intermediate hubs.