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Port of Spain

$301+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 July 2, 2025.

Round-trip from

$483
(Kiwi.com)

One-way from

$301
(JetBlue)

Popular in

February

Cheapest in

January

Average price

$847
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. 18% potential increase in price ($165 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($62 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 2, 2025.

This Mytrip deal was found by Cheapflights users on 7/1. 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.
Thu 9/1110:27 amORD - POS
1 stop16h 48mMultiple Airlines
Tue 9/239:10 amPOS - ORD
3 stops32h 02mMultiple Airlines
Deal found 7/1$516
This Copa Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 10/223:07 pmORD - POS
1 stop9h 41mCopa Airlines
Sat 10/253:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Deal found 7/2$533
This Air Canada deal was found by Cheapflights users on 7/1. 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 7/142:00 pmORD - POS
1 stop10h 20mAir Canada
Mon 7/212:20 amPOS - ORD
2 stops17h 26mAir Canada
Deal found 7/1$537
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/166:16 amORD - POS
1 stop10h 48mJetBlue
Wed 7/238:50 amPOS - ORD
1 stop14h 43mJetBlue
Deal found 7/2$547
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 10/106:00 amORD - POS
1 stop14h 20mAmerican Airlines
Mon 10/207:00 amPOS - ORD
1 stop16h 31mAmerican Airlines
Deal found 6/30$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 July 2, 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

Mon 7/14

8:09 am-6:55 pm

1 stop9h 46m

Port of Spain Piarco Intl

Mon 8/25

3:49 am-9:22 am

2 stops30h 33m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 8/7

7:55 am-1:46 am

1 stop16h 51m

Port of Spain Piarco Intl

Mon 8/11

2:38 pm-12:21 am

1 stop10h 43m

$516

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/14

10:40 am-1:20 am

2 stops13h 40m

Port of Spain Piarco Intl

Sun 7/20

2:20 am-6:53 pm

2 stops17h 33m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 7/16

6:16 am-6:04 pm

1 stop10h 48m

Port of Spain Piarco Intl

Wed 7/23

8:50 am-10:33 pm

1 stop14h 43m

$547

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

7:15 pm-2:16 pm

1 stop18h 01m

Port of Spain Piarco Intl

Fri 9/26

3:25 pm-11:48 pm

1 stop9h 23m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/28

10:35 am-11:23 pm

1 stop11h 48m

Port of Spain Piarco Intl

Thu 8/14

12:30 am-9:33 pm

1 stop22h 03m

$621

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 8/15

6:15 am-6:04 pm

1 stop10h 49m

$301

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

8:02 am-10:15 pm

2 stops12h 13m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 8/15

4:45 pm-11:23 pm

2 stops29h 38m

$1,122

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 July 2, 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 July 2, 2025.
Read reviews from past customers who have flown Copa Airlines, United Airlines, and JetBlue 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.
Copa Airlines
7.5
Good
1,465 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,465 reviews
Copa Airlines
7.5
Good
1,465 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,861 reviews
Copa Airlines
7.5
Good
1,465 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
JetBlue
7.3
Good
2,918 reviews
Copa Airlines
7.5
Good
1,465 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,465 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,669 reviews
Copa Airlines
7.5
Good
1,465 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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 2 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, Copa Airlines ($516), Air Canada ($537), and American Airlines ($548) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Copa Airlines is 28% 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
St. Louis to Port of Spain flights
O'Hare Intl to Scarborough flights

Top 2 airlines flying from Chicago to Port of Spain

Discover the top 2 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$615FlexibilityNo cancel feeOn-time71%

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