HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Port of Spain

$254+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Port of Spain with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 28, 2026.

This Trip.com deal was found by Cheapflights users on 4/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:15 pm
ORD
-
POS
1 stop31h 05m
Air Canada
Thu 4/301:25 am
POS
-
ORD
1 stop19h 15m
Air Canada
Deal found 4/23$499
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:52 am
ORD
-
POS
1 stop11h 08m
Multiple Airlines
Mon 6/2210:10 am
POS
-
ORD
1 stop30h 17m
Multiple Airlines
Deal found 4/26$507
This Expedia deal was found by Cheapflights users on 4/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:55 am
ORD
-
POS
1 stop15h 25m
Air Canada
Sun 5/31:25 am
POS
-
ORD
1 stop16h 34m
Air Canada
Deal found 4/25$517
This Air Canada deal was found by Cheapflights users on 4/25. 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 4/259:20 pm
ORD
-
POS
1 stop26h 00m
Air Canada
Fri 5/11:25 am
POS
-
ORD
1 stop13h 00m
Air Canada
Deal found 4/25$522
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:05 am
ORD
-
POS
1 stop13h 55m
Multiple Airlines
Sun 5/3110:10 am
POS
-
ORD
1 stop27h 27m
Multiple Airlines
Deal found 4/24$533
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:50 pm
ORD
-
POS
2 stops28h 05m
Multiple Airlines
Wed 6/179:10 am
POS
-
ORD
1 stop27h 53m
Multiple Airlines
Deal found 4/26$542
This FlightHub deal was found by Cheapflights users on 4/26. 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.
Thu 6/186:22 pm
ORD
-
POS
2 stops28h 53m
Air Canada
Sun 6/211:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 4/26$556
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:15 pm
ORD
-
POS
1 stop9h 00m
Multiple Airlines
Fri 5/159:10 am
POS
-
ORD
1 stop15h 46m
Multiple Airlines
Deal found 4/24$557

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$507
(Kiwi.com)

One-way from

$254
(Air Canada)

Popular in

December

Cheapest in

February

Average price

$482
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. 37% potential increase in price ($399 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($93 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 28, 2026.
Use the filters below to find and compare flights from Chicago to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/28

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Sun 5/31

10:10 am-12:37 pm

1 stop27h 27m

$533

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/25

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Sun 5/31

10:10 am-7:55 am

2 stops22h 45m

$589

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/10

8:51 am-11:23 pm

1 stop13h 32m

Port of Spain Piarco Intl

Tue 6/16

12:30 am-10:20 am

1 stop10h 50m

$630

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 6/21

1:00 am-1:16 pm

1 stop11h 16m

Port of Spain Piarco Intl

Sun 6/28

3:49 am-2:06 pm

1 stop11h 17m

$633
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 6/18

3:21 pm-1:46 am

1 stop9h 25m

Port of Spain Piarco Intl

Sat 6/20

3:49 am-2:06 pm

1 stop11h 17m

$633

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 7/3

1:15 pm-12:50 am

1 stop10h 35m

Port of Spain Piarco Intl

Thu 7/9

12:30 am-10:20 am

1 stop10h 50m

$650

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 6/18

7:07 pm-12:15 am

3 stops28h 08m

Port of Spain Piarco Intl

Sun 6/21

1:25 am-7:46 pm

3 stops19h 21m

$659

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 6/23

8:00 am-11:00 pm

2 stops14h 00m

Port of Spain Piarco Intl

Wed 7/8

7:00 am-7:43 pm

2 stops13h 43m

$678
Cheapest one-way

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 5/1

6:21 pm-12:15 am

2 stops52h 54m

$254

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/2

8:35 pm-12:15 am

1 stop26h 40m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 11 resultsSorted by cheapest first
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 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, June is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $317). Flying from Chicago to Port of Spain in January is currently the most expensive (average of $638). 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 44% 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 April 28, 2026.
Read reviews from past customers who have flown American Airlines and Air Canada 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.
American Airlines
7.1
Good
11,680 reviews

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,680 reviews
American Airlines
7.1
Good
11,680 reviews

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
Air Canada
7.1
Good
10,979 reviews
American Airlines
7.1
Good
11,680 reviews

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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 4 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 $633, United Airlines can have you in Port of Spain from Chicago in 11h 16m. The distance from Chicago to Port of Spain is about 2697 mi. This flight may include one or multiple stops.

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

    According to our current data, Air Canada ($392), Copa Airlines ($472), and American Airlines ($548) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Air Canada is 42% 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, June is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $317). Flying from Chicago to Port of Spain in January is currently the most expensive (average of $638). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 4 airlines flying from Chicago to Port of Spain

Discover the top 4 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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$392Average$516FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$472Average$597FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$548Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$629FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.