Cheap flights from Chicago (CHI) to Port of Spain (POS)

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The best prices from Chicago to Port of Spain Piarco Intl are usually found in August or June, booked 60 days in advance, depart on a Monday or Friday and return on a Friday

How to find the cheapest flight from
Chicago (CHI) to Port of Spain (POS)

All the information you need to plan the best CHI to POS flight in 2021: compare Chicago to Port of Spain flight prices with the expected peak season, weather and rainfall in Port of Spain.
CHI - POS
Price
$231 - $840
POS
Temperature
77 - 80.6 °F
POS
Precipitation
1.2 - 9.8 inches

Popular in

December

High demand for flights, 36% potential price rise

Cheapest in

August

Best time to find cheap flights, 57% potential price drop

Round-trip from

$231

From Chicago (CHI) to Port of Spain Piarco Intl

One-way from

$211

One-way flight from Chicago (CHI) to Port of Spain Piarco Intl

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Port of Spain?

It’s generally more expensive to depart on a Sunday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

How far in advance should I book a flight from Chicago to Port of Spain?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 61 days in advance, which can save you up to 6% on flights from Chicago to Port of Spain compared to booking the week you need them. Waiting 61 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $585. For sooner than that we have options available in the next 3 days from $628.

When is the cheapest time to fly from Chicago to Port of Spain (CHI - POS)?

A simple way to save on the total cost of your ticket is to fly from Chicago to Port of Spain in the afternoon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the evening.

What is the cheapest month to fly from Chicago to Port of Spain?

Flights from Chicago to Port of Spain lean towards being more expensive in December. Prices are generally better when you fly from Chicago to Port of Spain in August, with the cheapest ticket starting at $231.

Cheap flights from Chicago to Port of Spain in November, December 2021

The best prices found for CHI to POS flights for November, December
9 Dec - 11 Dec
$350pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Dec - 12 Dec
$417pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Dec - 11 Dec
$441pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl

Chicago to Port of Spain 2022 flight deals

Cheap flights to Port of Spain from Chicago found for next year
9 Dec - 11 Dec
$350pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Dec - 12 Dec
$417pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Dec - 11 Dec
$441pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl

One-way flights to Piarco Intl from Chicago

The cheapest one-way flights from Chicago to Port of Spain
4:15 am - 1:45 pm
Multiple Airlines
1 Stop
31h 30m
ORD - POS
Multiple Airlines
$211
Kiwi.com
2:45 am - 7:27 pm
United Airlines
1 Stop
14h 42m
ORD - POS
United Airlines
$265
United
4:15 am - 1:45 pm
Multiple Airlines
1 Stop
31h 30m
ORD - POS
Multiple Airlines
$484
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Port of Spain</span> flights.

Flight FAQs

From Chicago to Port of Spain

What airport do you fly into for flights to Port of Spain from Chicago?

Port of Spain Piarco Intl (POS) is the airport you will fly into if you book a flight from Chicago to Port of Spain. You should not have trouble finding flights to Piarco Intl from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights to the Port of Spain airport from Chicago. It is only a 12.7 mi journey from Piarco Intl (POS) to Port of Spain’s city center.

Which airlines flying from Chicago to Port of Spain Piarco Intl have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, United Airlines, and Air Canada flying from Chicago to Port of Spain Piarco Intl have implemented new flexible cancellation policies.

Can I find flights from Chicago to Port of Spain for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Port of Spain for under $400. The cheapest flight booked recently is on Multiple Airlines for just $311, but on average you can expect to pay $349.

What is the cheapest airline to fly from Chicago to Port of Spain round-trip?

According to our current data, JetBlue ($427), offers the cheapest pricing from Chicago to Port of Spain. Users have found that JetBlue is 21% cheaper than the other options available to this destination.

What are the cheapest flights from Chicago to Port of Spain?

Looking at all options, your cheapest flight can be booked for $224. While the most popular route (Chicago O'Hare Intl - Port of Spain Piarco Intl) can be booked for $311 on average our data indicates $394 when flying from Chicago to Port of Spain.

What are the most popular airlines that fly from Chicago to Port of Spain?

Before booking your flight from Chicago to Port of Spain check out the most popular airlines for this route: Major Airline, American Airlines or Air Canada.

COVID Restrictions

View COVID Travel Restrictions for Port of Spain, Trinidad and Tobago

Do I need a COVID test to fly to Port of Spain from Chicago?

Information is based on travel restrictions from Chicago to Port of Spain Piarco Intl

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Port of Spain Piarco Intl.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Port of Spain Piarco Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Port of Spain Piarco Intl.

Do I need a test to fly back to Chicago from Port of Spain?

Returning to Chicago from Port of Spain Piarco Intl

COVID-19 testing requirements
Visitors from Port of Spain Piarco Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Port of Spain Piarco Intl are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Port of Spain, Trinidad and Tobago

Destination information for Port of Spain

Things to know before you go - useful duration and weather info for your trip from Chicago to Port of Spain.
Today's exchange rate
$1 = $6.66
Average temperature for November in Port of Spain
89.6 °F
Avg rainfall for November in Port of Spain
7.9 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Port of Spain

Top 3 airlines flying from Chicago to Port of Spain Piarco Intl

The chart below displays the airlines Cheapflights users traveling from Chicago to Port of Spain choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
United Airlines
$237 $525 No cancel fee 69%
American Airlines
$239 $558 No cancel fee 71%
Air Canada
$276 $465 No cancel fee 67%
Home Caribbean Trinidad and Tobago Port of Spain Cheap flights from Chicago to Port of Spain