The cheapest times to fly from POS to ORD are

  • January 15th to February 11th
  • March 5th to June 3rd (except the weeks of March 26th and April 2nd)
  • September 3rd to November 18th

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from POS to ORD is late September. Prices can be as high as $1026 for Sunday flights during early to mid December, or as low as $422 for Tuesday flights around late September.


When to Fly to Chicago

Flying from Port of Spain (POS) to Chicago, IL (ORD) will usually cost between $438 to $800 per person if booking more than four weeks in advance. On average the very cheapest time to fly is late September with an average ticket price of $438. Due to high demand the most expensive time to fly is early to mid December, with an average price of $874. Planning your trip to low-cost times can easily save you $436 on economy flights and even more on first-class flights. Generally, any price below $531 can be considered a good price for a round-trip POS to ORD flight.

See below for a graph of average weekly prices for the POS to ORD route. All prices are for round-trip tickets in USD.

POS to ORD Flight Prices

Compared to other flights, the POS to ORD flight is cheaper than the average and costs less than the average flight leaving from Port of Spain. The average price per mile (for a direct flight) is $0.12, which is far below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $57 (10%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $526. Return trip prices are from the ORD to POS flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from POS to ORD can generally find a 1-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 5 hour 50 minutes may not be realistic.


Flight Hacking POS to ORD

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from POS to ORD — but Champion Traveler does!

Hack #1: Miami, FL (POS > MIA > ORD)

  • Price for both tickets: $510
  • Average savings: $21 (3.95%)

See POS to FLL flights

Hack #2: Fort Lauderdale, FL (POS > FLL > ORD)

  • Price for both tickets: $522
  • Average savings: $9 (1.69%)

See POS to MIA flights


Flight Questions Answered

Still have questions about flying from POS to ORD? We’ve got answers.

Which airlines fly this route?

You can find 8 major airlines flying this route most often: Air Canada, American, Caribbean Airlines, COPA, Delta, JetBlue, United, WestJet, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to Piarco Airport?

The distance between the two airports is roughly 2698 miles or 4342 kilometers.

How long does it take to fly from POS to ORD?

The real-world flight time for a nonstop POS to ORD flight is about 5 hour 50 minutes.

How many flights go between Port of Spain and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 52 available flights from POS to ORD.


Airport Location Info


Departing Airport

Origination code POS
Origination airport name Piarco Airport
City Port of Spain
Country Trinidad and Tobago
Latitude 10.6
Longitude -61.3

Return Airport

Destination code ORD
Destination airport name Chicago O’Hare International Airport
City Chicago, IL
Country the United States
Latitude 42
Longitude -87.9


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.