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Port of Spain

$155+ Cheap flights from Chicago (CHI) to Port of Spain (POS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Mar 26 — Apr 21
Thu 3/26
Thu 4/2
1 adult, Economy
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Cheap flight deals from Chicago to Port of Spain

Cheapest flights from Chicago to Port of Spain
Explore the most affordable flight options available from Chicago to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 24, 2026.

This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:15 pm
ORD
-
POS
1 stop9h 00m
Air Canada
Wed 9/21:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Deal found 2/23$298
This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/288:40 pm
ORD
-
POS
1 stop26h 40m
Air Canada
Fri 4/31:20 am
POS
-
ORD
2 stops18h 33m
Air Canada
Deal found 2/23$303
This Travelocity deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:22 pm
ORD
-
POS
2 stops52h 53m
Air Canada
Fri 6/51:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 2/23$308
This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/39:50 am
ORD
-
POS
1 stop13h 30m
Air Canada
Fri 4/101:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/23$348
This Orbitz deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 am
ORD
-
POS
1 stop13h 20m
Air Canada
Sun 5/241:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 2/22$358
This FlightHub deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
ORD
-
POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/20$363
This Priceline deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:40 am
ORD
-
POS
2 stops14h 40m
Air Canada
Sun 4/261:20 am
POS
-
ORD
2 stops18h 33m
Air Canada
Deal found 2/23$366
This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:25 pm
ORD
-
POS
1 stop28h 55m
Air Canada
Thu 3/191:20 am
POS
-
ORD
2 stops31h 40m
Air Canada
Deal found 2/23$368
This Air Canada deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:15 am
ORD
-
POS
2 stops16h 05m
Air Canada
Thu 3/191:20 am
POS
-
ORD
2 stops31h 40m
Air Canada
Deal found 2/23$371

Find flight deals from Chicago to Port of Spain

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Port of Spain (POS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$308
(Travelocity)

One-way from

$155
(Travelocity)

Popular in

December

Cheapest in

February

Average price

$475
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
Search Deals
From Chicago (CHI) to Port of Spain Piarco Intl
Search Deals
One-way flight from Chicago (CHI) to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 34% potential increase in price ($375 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($90 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Port of Spain that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 24, 2026.
Use the filters below to find and compare flights from Chicago to Port of Spain that are best for you.

Fly from

Chicago

Fly to

Port of Spain

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 6/1

10:00 am-12:15 am

1 stop13h 15m

Port of Spain Piarco Intl

Fri 6/5

1:25 am-1:25 pm

1 stop13h 00m

$298

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

$363

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

8:00 am-12:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Thu 3/19

1:20 am-8:00 am

2 stops31h 40m

$438

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

6:04 pm-12:20 am

2 stops53h 16m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-7:45 pm

1 stop19h 25m

$508

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Fri 3/20

1:20 am-3:10 pm

1 stop14h 50m

$528

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

9:32 pm-12:20 am

2 stops25h 48m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-6:53 pm

2 stops18h 33m

$551

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/19

7:31 pm-12:20 am

2 stops27h 49m

Port of Spain Piarco Intl

Thu 3/26

1:20 am-11:18 am

2 stops34h 58m

$557

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/3

6:21 pm-12:20 am

2 stops52h 59m

$155

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

10:00 am-12:20 am

1 stop13h 20m

$190

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/23

8:40 pm-12:20 am

1 stop26h 40m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Showing 1-10 of 12 results
1
2

Compare providers for flights from Chicago to Port of Spain

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Port of Spain in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Port of Spain flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Port of Spain flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Port of Spain flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Port of Spain flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Port of Spain flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Port of Spain

What is the cheapest month to book a flight from Chicago to Port of Spain?

Currently, November is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $435). Flying from Chicago to Port of Spain in January is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Port of Spain?

What’s the top layover airport for flights from Chicago to Port of Spain?

Share of 1-stop round-trip flights from Chicago to Port of Spain chosen by Cheapflights users in the past 12 months, using the same layover each way.

Miami (MIA) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Port of Spain on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Port of Spain?

Average round-trip fare for 1-stop flights from Chicago to Port of Spain, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $432.

What’s the fastest layover option from Chicago to Port of Spain?

Shortest average travel time for 1-stop one-way flights from Chicago to Port of Spain, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Miami (MIA) have the shortest average one-way travel time for 1-stop routes: 8h 03m.

Which airport typically offers the quickest layover for flights from Chicago to Port of Spain?

Average layover duration for 1-stop one-way flights from Chicago to Port of Spain, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 14m.

Reviews of airlines servicing Port of Spain

Get insights into the airlines that provide service to Port of Spain. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Port of Spain. Reviews last updated February 24, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Chicago to Port of Spain. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,344 reviews

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,344 reviews
United Airlines
7.4
Good
9,344 reviews

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,344 reviews
United Airlines
7.4
Good
9,344 reviews

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Chicago to Port of Spain. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 12.6 mi journey from Piarco Intl (POS) to Port of Spain’s city center.

  • How long is the flight from Chicago to Port of Spain?

    For as low as $308, Air Canada can have you in Port of Spain from Chicago in 9h. The distance from Chicago to Port of Spain is about 2697 mi.

  • What are the cheapest airlines flying from Chicago to Port of Spain round-trip?

    According to our current data, Air Canada ($432), American Airlines ($548), and United Airlines ($548) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Air Canada is 38% cheaper than the other options available to this destination.

  • Can I find deals for flights from Chicago to Port of Spain that include hotel bookings?

    Yes. In addition to deals on Chicago to Port of Spain flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Port of Spain?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Port of Spain.

  • Can I find deals for business class flights from Chicago to Port of Spain?

    Yes. Cheapflights offers flight deals from Chicago to Port of Spain by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Port of Spain?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $435). Flying from Chicago to Port of Spain in January is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Port of Spain

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Port of Spain flights

Top 3 airlines flying from Chicago to Port of Spain

Discover the top 3 airlines that operate flights from Chicago to Port of Spain. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$548Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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