Chicago to Port Of Spain flights

Routavio compares airline fares from several flight booking sites. The lowest one-way fare it found for Chicago to Port Of Spain is €258 with Copa Airlines (checked on 8 Oct 2026).

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Lowest observed

€258

Average observed

€349

Cheapest month

November 2026

Last checked

15 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €258

Lowest observed

15 Nov 2026

Copa Airlines · 3 stops · One way

Cheapest observed day · Last checked: 8 Oct 2026

Departure

06:00

When to fly

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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.

Prices are for observed departure and return date pairs. No data does not mean no flights.

Lowest observed: €258, departing 15 Nov 2026 (Last checked: 8 Oct 2026)One-way fareCheck live prices for this route
Airlines seen: Air Canada, Allegiant Air, American Airlines, Caribbean Airlines, Copa Airlines, Frontier Airlines +2 more
Typical journey time: 19h 23m

Short answer

Routavio has seen Air Canada fares from Chicago to Port Of Spain. The lowest fare Routavio's own searches returned is €258, seen on 8 Oct 2026. The average across the fares we caught is €349. November 2026 is the cheapest month in our observations, at €258. These are prices Routavio's searches returned on the dates shown, not quotes; run a live search for today's fare.

About this route

Explore the fares we observed from Chicago to Port Of Spain. Prices move often, so pick your dates to see the latest options.

Route distance: 4,318 km
Typical journey time: 19h 23m
Airlines seen: Air Canada, Allegiant Air, American Airlines, Caribbean Airlines, Copa Airlines, Frontier Airlines +2 more
Seen on fares with a connection: Frontier Airlines, Air Canada, JetBlue, United Airlines, American Airlines, Caribbean Airlines +2 more
Alternative airports: CGX, DPA, MDW, PWK, RFD

Route-level information; individual journeys vary.
We have not observed non-stop service on this route; the fares shown include at least one stop.

A clearer picture of your fare

Observed, not guaranteed

Every price is a fare we actually saw, and it may change at any time.

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The price is final on the provider's site, where your booking is completed.

How our prices work

Airport to city: straight-line distance

Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.
Piarco International Airport (POS) → Port Of Spain, city gazetteer reference point (10.6021, -61.3394): ≈ 1 km.

Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.

Lowest one-way fare we saw per airline

Cheapest airline from Chicago to Port Of Spain: Caribbean Airlines, from €258 (checked 8 Oct 2026).

Lowest one-way fare we saw per airline
Airline	Lowest fare	Priced days
Caribbean Airlines	€258Nov 26, 2026	6
Copa Airlines	€258Nov 15, 2026	5
Frontier Airlines	€264Nov 8, 2026	34
Air Canada	€270Oct 16, 2026	16
JetBlue	€273Oct 28, 2026	15
American Airlines	€302Jan 11, 2027	6
United Airlines	€302Dec 9, 2026	14

One-way fares checked in the last 14 days. An airline listed here had a fare on at least 3 departure days. Each figure is the lowest we saw, not a guaranteed fare. Connecting itineraries are included; the date is the departure day of that fare.

Frequently asked

How much is a flight from Chicago to Port Of Spain?

The lowest fare we have observed is €258, found on 8 Oct 2026. Prices move, so read it as a floor rather than a quote.

When is the cheapest month to fly from Chicago to Port Of Spain?

In our observations November 2026 is the cheapest month so far, at €258.

Are there direct flights from Chicago to Port Of Spain?

Our data holds no non-stop flight from Chicago to Port Of Spain. The fares on this page include at least one stop.

Which airlines fly from Chicago to Port Of Spain?

These are the carriers we have seen on the route: Air Canada, Allegiant Air, American Airlines, Caribbean Airlines, Copa Airlines, Frontier Airlines +2 more.

How long does the flight from Chicago to Port Of Spain take?

The average journey time across the 85 fares we observed is 23h 20m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.

How many of the observed Chicago to Port Of Spain fares were non-stop?

None of the 85 fares we observed was non-stop; every one included at least one stop. That describes our observations, not every flight that operates.

Which airline has the lowest fare from Chicago to Port Of Spain?

Cheapest airline from Chicago to Port Of Spain: Caribbean Airlines, from €258 (checked 8 Oct 2026).

How observed prices work, what "No data" means and what a fare includes: Read the flight price guide