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

$188+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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

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 September 16, 2025.

Round-trip from

$423
(Air Canada)

One-way from

$188
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$618
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. 6% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($66 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 16, 2025.

This Air Canada deal was found by Cheapflights users on 9/14. 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.
Mon 9/152:00 pmORD - POS
1 stop10h 20mAir Canada
Fri 9/262:25 amPOS - ORD
1 stop11h 49mAir Canada
Deal found 9/14$423
This Air Canada deal was found by Cheapflights users on 9/13. 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 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Fri 11/282:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 9/13$428
This Air Canada deal was found by Cheapflights users on 9/13. 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 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Thu 11/272:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 9/13$473
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/227:43 pmORD - POS
2 stops29h 03mMultiple Airlines
Sun 10/266:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Deal found 9/15$492
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/41:35 pmORD - POS
2 stops21h 42mMultiple Airlines
Thu 12/119:10 amPOS - ORD
1 stop29h 20mMultiple Airlines
Deal found 9/15$519
This Copa Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 10/63:07 pmORD - POS
1 stop9h 39mCopa Airlines
Wed 10/82:40 pmPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 9/14$532
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/147:43 pmORD - POS
2 stops29h 03mMultiple Airlines
Tue 10/218:55 amPOS - ORD
1 stop28h 50mMultiple Airlines
Deal found 9/16$536
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 9/187:00 amORD - POS
1 stop15h 23mUnited Airlines
Wed 10/1512:30 amPOS - ORD
1 stop10h 40mUnited Airlines
Deal found 9/14$548

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 September 16, 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

Fri 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 2/2

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Sun 2/8

2:15 am-3:10 pm

1 stop14h 55m

$423

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-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/6

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 3/12

1:15 am-8:05 am

2 stops31h 50m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:43 pm-1:46 am

2 stops29h 03m

Port of Spain Piarco Intl

Sun 10/26

6:25 pm-9:22 am

1 stop15h 57m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-1:01 pm

1 stop12h 46m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/6

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Wed 10/8

2:40 pm-12:21 am

1 stop10h 41m

$532

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/5

10:35 am-12:23 am

1 stop11h 48m

Port of Spain Piarco Intl

Mon 1/12

1:30 am-7:50 pm

1 stop20h 20m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 12/4

7:35 am-12:23 am

1 stop14h 48m

Port of Spain Piarco Intl

Wed 12/10

1:30 am-2:41 pm

1 stop15h 11m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:10 am-11:23 pm

1 stop15h 13m

Port of Spain Piarco Intl

Sat 10/25

12:30 am-10:53 am

1 stop11h 23m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 18 results
1
2

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 $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 September 16, 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.

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 September 16, 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
8,924 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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 $423, Air Canada can have you in Port of Spain from Chicago in 9h 10m. 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, United Airlines ($480), American Airlines ($487), and Air Canada ($516) offers the cheapest pricing from Chicago to Port of Spain. Users have found that United Airlines is 36% 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

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
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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$622FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$566FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$516Average$556FlexibilityNo cancel feeOn-time67%

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.