Port Of Spain to Chicago flights

Routavio compares airline fares from several flight booking sites. The lowest one-way fare it found for Port Of Spain to Chicago is €245 with Caribbean Airlines (checked on 7 Oct 2026).

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Lowest observed

€245

Average observed

€354

Cheapest month

October 2026

Last checked

14 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €245

Lowest observed

29 Oct 2026

Caribbean Airlines · 1 stop · One way

Cheapest observed day · Last checked: 7 Oct 2026

Departure

10:10

When to fly

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Find the dates that work for you

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: €245, departing 29 Oct 2026 (Last checked: 7 Oct 2026)One-way fareCheck live prices for this route
Airlines seen: Air Canada, American Airlines, Caribbean Airlines, Copa Airlines, Frontier Airlines, JetBlue +1 more
Typical journey time: 24h 10m

Short answer

Routavio has seen Air Canada fares from Port Of Spain to Chicago. The lowest fare Routavio's own searches returned is €245, seen on 7 Oct 2026. The average across the fares we caught is €354. October 2026 is the cheapest month in our observations, at €245. 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 Port Of Spain to Chicago. Prices move often, so pick your dates to see the latest options.

Route distance: 4,318 km
Typical journey time: 24h 10m
Airlines seen: Air Canada, American Airlines, Caribbean Airlines, Copa Airlines, Frontier Airlines, JetBlue +1 more
Seen on fares with a connection: Caribbean Airlines, Air Canada, Frontier Airlines, Copa Airlines, United Airlines, American Airlines +1 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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We show like-for-like journeys so the comparison is fair.

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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

Piarco International Airport (POS) → Port Of Spain, city gazetteer reference point (10.6021, -61.3394): ≈ 1 km.
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.

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 Port Of Spain to Chicago: Caribbean Airlines, from €245 (checked 7 Oct 2026).

Lowest one-way fare we saw per airline
Airline	Lowest fare	Priced days
Caribbean Airlines	€245Oct 29, 2026	52
Frontier Airlines	€293Dec 11, 2026	7
JetBlue	€303Nov 12, 2026	7
Copa Airlines	€328Nov 4, 2026	5
Air Canada	€342Oct 19, 2026	7
United Airlines	€377Dec 18, 2026	3

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 Port Of Spain to Chicago?

The lowest fare we have observed is €245, found on 7 Oct 2026. Prices move, so read it as a floor rather than a quote.

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

In our observations October 2026 is the cheapest month so far, at €245.

Are there direct flights from Port Of Spain to Chicago?

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

Which airlines fly from Port Of Spain to Chicago?

These are the carriers we have seen on the route: Air Canada, American Airlines, Caribbean Airlines, Copa Airlines, Frontier Airlines, JetBlue +1 more.

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

The average journey time across the 89 fares we observed is 26h 14m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.

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

None of the 90 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 Port Of Spain to Chicago?

Cheapest airline from Port Of Spain to Chicago: Caribbean Airlines, from €245 (checked 7 Oct 2026).

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