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Port of Spain

$193+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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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 October 22, 2025.

This Air Canada deal was found by Cheapflights users on 10/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:15 pmORD - POS
1 stop26h 55mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 10/19$433
This Trip.com deal was found by Cheapflights users on 10/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/35:10 amORD - POS
1 stop12h 50mMultiple Airlines
Fri 11/710:10 amPOS - ORD
1 stop16h 17mMultiple Airlines
Deal found 10/20$437
This Trip.com deal was found by Cheapflights users on 10/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/222:01 pmORD - POS
1 stop14h 09mMultiple Airlines
Thu 11/2712:10 amPOS - ORD
1 stop16h 21mMultiple Airlines
Deal found 10/19$441
This Air Canada deal was found by Cheapflights users on 10/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:00 amORD - POS
1 stop15h 10mAir Canada
Sun 11/302:15 amPOS - ORD
1 stop19h 15mAir Canada
Deal found 10/22$443
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:45 amORD - POS
1 stop9h 15mMultiple Airlines
Mon 12/12:38 pmPOS - ORD
2 stops50h 19mMultiple Airlines
Deal found 10/22$477
This Air Canada deal was found by Cheapflights users on 10/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:05 pmORD - POS
2 stops53h 05mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 10/20$493
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2411:48 amORD - POS
1 stop23h 17mMultiple Airlines
Mon 12/12:38 pmPOS - ORD
2 stops50h 19mMultiple Airlines
Deal found 10/22$494
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2311:48 amORD - POS
1 stop30h 12mMultiple Airlines
Mon 12/12:38 pmPOS - ORD
2 stops50h 19mMultiple Airlines
Deal found 10/22$495
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:41 pmORD - POS
2 stops15h 50mMultiple Airlines
Wed 12/179:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 10/20$502

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$433
(Air Canada)

One-way from

$193
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$575
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.
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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. 17% potential increase in price ($146 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 22, 2025.
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

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-1:01 pm

1 stop12h 46m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 11/23

10:00 am-1:10 am

1 stop13h 10m

Port of Spain Piarco Intl

Sun 11/30

2:15 am-7:30 pm

1 stop19h 15m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 11/3

7:34 pm-1:05 pm

1 stop15h 31m

Port of Spain Piarco Intl

Fri 11/7

2:26 pm-9:47 am

2 stops21h 21m

$474

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

8:45 am-8:00 pm

1 stop9h 15m

Port of Spain Piarco Intl

Mon 12/1

2:38 pm-2:57 pm

2 stops50h 19m

$477

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/31

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Thu 2/5

2:15 am-2:55 pm

2 stops14h 40m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

6:05 pm-1:10 am

2 stops53h 05m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-1:01 pm

1 stop12h 46m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 11/24

10:38 am-1:10 am

2 stops36h 32m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-2:55 pm

2 stops14h 40m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

12:50 pm-1:10 am

2 stops34h 20m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-6:55 pm

2 stops18h 40m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/9

7:15 am-1:10 am

2 stops15h 55m

$193

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/9

6:11 pm-8:20 pm

3 stops24h 09m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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, October is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $449). Flying from Chicago to Port of Spain in July is currently the most expensive (average of $613). 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 October 22, 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 43% on your trip compared to booking a flight in the evening.

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.

Panama City (PTY) – 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 Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 8h 30m.

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 October 22, 2025.
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
8,990 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,990 reviews
United Airlines
7.4
Good
8,990 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,028 reviews
United Airlines
7.4
Good
8,990 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 $433, Air Canada can have you in Port of Spain from Chicago in 26h 55m. 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 ($487), and United Airlines ($560) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Air Canada is 37% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Port of Spain one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $193. However, be on the lookout for offers from Copa Airlines and American Airlines, as they are both options that can get you from Chicago to Port of Spain for a low price.

  • 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 $449). Flying from Chicago to Port of Spain in July is currently the most expensive (average of $613). 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
St. Louis to Port of Spain flights
O'Hare Intl to Scarborough 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$487Average$564FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$560Average$628FlexibilityNo cancel feeOn-time69%

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