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$290+ 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap 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 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$302
(Kiwi.com)

One-way from

$290
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$1,342
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
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From Chicago (CHI) to Port of Spain Piarco Intl
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One-way flight from Chicago (CHI) to Port of Spain Piarco Intl
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Highest demand for flights based on searches. 22% potential increase in price ($202 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($59 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find 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 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/268:42 pmORD - POS
1 stop18h 59mMultiple Airlines
Thu 4/176:01 pmPOS - ORD
2 stops21h 25mMultiple Airlines
Deal found 2/19$302
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/199:12 amORD - POS
2 stops30h 29mFrontier
Sun 3/236:01 pmPOS - ORD
2 stops47h 37mFrontier
Deal found 2/20$398
This Copa Airlines deal was found by Cheapflights users on 2/19. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/253:07 pmORD - POS
1 stop9h 40mCopa Airlines
Wed 8/132:35 pmPOS - ORD
1 stop10h 47mCopa Airlines
Deal found 2/19$486
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/192:50 pmORD - POS
1 stop22h 15mAmerican Airlines
Sun 3/233:15 pmPOS - ORD
1 stop18h 50mAmerican Airlines
Deal found 2/20$555
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/67:45 amORD - POS
1 stop14h 38mUnited Airlines
Sat 4/1212:30 amPOS - ORD
1 stop10h 41mUnited Airlines
Deal found 2/20$628

Find flights from Chicago to Port of Spain within your budget

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 20, 2025.

Fly from

Chicago

Fly to

Port of Spain

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 3/26

8:42 pm-4:41 pm

1 stop18h 59m

Port of Spain Piarco Intl

Thu 4/17

6:01 pm-2:26 pm

2 stops21h 25m

$302

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 3/19

9:12 am-4:41 pm

2 stops30h 29m

Port of Spain Piarco Intl

Sun 3/23

6:01 pm-4:38 pm

2 stops47h 37m

$398

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 7/25

3:07 pm-1:47 am

1 stop9h 40m

Port of Spain Piarco Intl

Wed 8/13

2:35 pm-12:22 am

1 stop10h 47m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 3/19

2:50 pm-2:05 pm

1 stop22h 15m

Port of Spain Piarco Intl

Sun 3/23

3:15 pm-9:05 am

1 stop18h 50m

$555

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 4/6

9:15 am-11:23 pm

1 stop13h 08m

Port of Spain Piarco Intl

Sat 4/12

12:30 am-11:31 am

1 stop12h 01m

$628

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/20

6:25 pm-8:00 pm

2 stops24h 35m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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

*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.

Travel insights for flights from Chicago to Port of Spain

Get recent, data-driven insights about flights from Chicago to Port of Spain including ideal travel times, pricing trends, and more.

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

Currently, October 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 December is currently the most expensive (average of $710). 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.

What is the cheapest time of day to fly from CHI to POS?

Find hourly flight availability from Chicago to Port of Spain. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

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 37% on your trip compared to booking a flight in the evening.

Rainfall in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Port of Spain ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Port of Spain when rainfall is around 1.2 in.

Temperature in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Port of Spain, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 20, 2025.
Peruse reviews from past customers who have flown with Copa Airlines, United Airlines and American Airlines from Chicago to Port of Spain to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Boarding

7.8

Food

6.9

Comfort

7.4

Overall

7.6

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Copa Airlines
7.6
Good
1,510 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Boarding

7.8

Food

6.9

Comfort

7.4

Overall

7.6

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

United Airlines
7.4
Good
8,766 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Boarding

7.8

Food

6.9

Comfort

7.4

Overall

7.6

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Boarding

7.8

Food

6.9

Comfort

7.4

Overall

7.6

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Frontier
6.0
Okay
3,355 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Boarding

7.8

Food

6.9

Comfort

7.4

Overall

7.6

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

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.

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

    According to our current data, Frontier ($398), Copa Airlines ($486), and American Airlines ($555) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Frontier 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, October 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 December is currently the most expensive (average of $710). 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

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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
O'Hare Intl to Scarborough flights
St. Louis 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$449Average$596FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$452Average$557FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$478Average$614FlexibilityNo cancel feeOn-time69%
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