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

According to our current data, Copa Airlines ($507), American Airlines ($517), and Frontier ($534) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Copa Airlines is 19% cheaper than the other options available to this destination.

What is the cheapest day to fly from Chicago to Port of Spain?

Travelers seeking maximum savings on their Chicago to Port of Spain flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Chicago to Port of Spain?

Before booking your flight from Chicago to Port of Spain check out the most popular airlines for this route: American Airlines, Copa Airlines or United Airlines.

What is the cheapest day to fly round-trip from Chicago to Port of Spain?

It’s generally more expensive to depart on a Saturday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

What is the cheapest month to fly from Chicago to Port of Spain?

Flights from Chicago to Port of Spain lean towards being more expensive in March. Prices are generally better when you fly from Chicago to Port of Spain in January, with the cheapest ticket starting at $476.

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.

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.

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.

$235+ Flights from Chicago to Port of Spain

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1. Tell us where you want to go

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Cheap flight deals from Chicago to Port of Spain

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$380 (Kiwi.com)
One-way from	$235 (American Airlines)
Popular in	March
Cheapest in	January
Average price	$837

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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High demand for flights, 12% potential price rise

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Best time to find cheap flights, 3% potential price drop

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Average for round-trip flights in December 2024

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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 December 22, 2024.

Mon 12/239:05 amORD - POS

1 stop31h 20mMultiple Airlines

Sun 1/53:29 pmPOS - ORD

2 stops32h 24mMultiple Airlines

Deal found 12/22

$938

Wed 12/256:19 pmORD - POS

1 stop28h 04mUnited Airlines

Wed 1/11:30 amPOS - ORD

1 stop22h 26mUnited Airlines

Deal found 12/22

$943

Fri 12/275:00 amORD - POS

1 stop15h 44mAmerican Airlines

Thu 1/27:05 amPOS - ORD

1 stop16h 30mAmerican Airlines

Deal found 12/22

$1,178

Best flights from Chicago to Port of Spain
Discover carefully curated flight deals from Chicago to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 22, 2024.

Wed 2/51:44 pmORD - POS

1 stop24h 45mMultiple Airlines

Tue 2/113:36 amPOS - ORD

2 stops22h 22mMultiple Airlines

Deal found 12/22

$380

Wed 2/56:55 amORD - POS

1 stop16h 38mCopa Airlines

Tue 2/113:36 amPOS - ORD

1 stop21h 51mCopa Airlines

Deal found 12/22

$507

Fri 1/1711:55 amORD - POS

1 stop9h 19mAmerican Airlines

Mon 1/276:00 amPOS - ORD

1 stop15h 19mAmerican Airlines

Deal found 12/22

$517

Wed 3/199:12 amORD - POS

2 stops30h 29mFrontier

Thu 3/276:01 pmPOS - ORD

2 stops44h 42mFrontier

Deal found 12/22

$534

Wed 2/58:50 amORD - POS

1 stop13h 33mUnited Airlines

Tue 2/111:30 amPOS - ORD

1 stop19h 40mUnited Airlines

Deal found 12/22

$607

Sun 6/18:25 pmORD - POS

1 stop28h 10mAir Canada

Fri 6/62:35 amPOS - ORD

1 stop9h 19mAir Canada

Deal found 12/22

$840

Last-minute flights from Chicago to Port of Spain
Discover last-minute flight deals from Chicago to Port of Spain. Data last updated December 22, 2024 and is based on user searches.

Fri 12/279:29 pmORD - POS

1 stop24h 54mUnited Airlines

Wed 1/11:30 amPOS - ORD

1 stop22h 26mUnited Airlines

Deal found 12/22

$943

Fri 12/275:00 amORD - POS

1 stop15h 44mAmerican Airlines

Thu 1/27:05 amPOS - ORD

1 stop16h 30mAmerican Airlines

Deal found 12/22

$1,178

Fri 12/275:00 amORD - POS

1 stop13h 00mMultiple Airlines

Mon 1/610:10 amPOS - ORD

1 stop11h 41mMultiple Airlines

Deal found 12/21

$1,481

Fri 1/31:57 pmORD - POS

1 stop9h 36mCopa Airlines

Tue 1/73:36 amPOS - ORD

1 stop10h 35mCopa Airlines

Deal found 12/22

$810

Fri 1/38:14 pmORD - POS

2 stops21h 46mMultiple Airlines

Wed 1/89:55 pmPOS - ORD

3 stops28h 56mMultiple Airlines

Deal found 12/22

$932

Fri 1/1711:55 amORD - POS

1 stop9h 19mAmerican Airlines

Mon 1/276:00 amPOS - ORD

1 stop15h 19mAmerican Airlines

Deal found 12/22

$517

Fri 1/177:35 amORD - POS

1 stop14h 48mUnited Airlines

Sun 1/261:30 amPOS - ORD

1 stop10h 44mUnited Airlines

Deal found 12/22

$607

One-way flights from Chicago to Port of Spain
Search for one-way flight options from Chicago to Port of Spain. Find affordable one-way fares based on user searches. Data last updated December 22, 2024.

Thu 1/3011:55 amORD - POS

1 stop9h 19mAmerican Airlines

Deal found 12/22

$235

Thu 1/306:28 pmORD - POS

3 stops24h 07mMultiple Airlines

Deal found 12/22

$1,613

Find flights from Chicago to Port of Spain within your budget

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 2/5

1:44 pm-4:29 pm

1 stop24h 45m

Port of Spain Piarco Intl

Tue 2/11

3:36 am-11:58 pm

2 stops22h 22m

$380

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 2/5

6:55 am-1:33 am

1 stop16h 38m

Port of Spain Piarco Intl

Tue 2/11

3:36 am-11:27 pm

1 stop21h 51m

$507

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/17

11:55 am-11:14 pm

1 stop9h 19m

Port of Spain Piarco Intl

Mon 1/27

6:00 am-7:19 pm

1 stop15h 19m

$517

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

Thu 3/27

6:01 pm-1:43 pm

2 stops44h 42m

$534

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 2/5

8:50 am-12:23 am

1 stop13h 33m

Port of Spain Piarco Intl

Tue 2/11

1:30 am-7:10 pm

1 stop19h 40m

$607

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 6/1

8:25 pm-1:35 am

1 stop28h 10m

Port of Spain Piarco Intl

Fri 6/6

2:35 am-10:54 am

1 stop9h 19m

$840

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/30

11:55 am-11:14 pm

1 stop9h 19m

$235

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/30

6:28 pm-8:35 pm

3 stops24h 07m

$1,613

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Compare providers for flights from Chicago to Port of Spain

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 December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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?

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

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

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

Peruse reviews from past customers who have flown with American Airlines and United 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

7.7

Good

1,712 reviews

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Copa Airlines

7.7

Good

1,712 reviews

Copa Airlines

7.7

Good

1,712 reviews

Reviews

1 / 10

United Airlines

7.4

Good

9,028 reviews

Copa Airlines

7.7

Good

1,712 reviews

Reviews

1 / 10

American Airlines

7.2

Good

10,000 reviews

Copa Airlines

7.7

Good

1,712 reviews

Reviews

1 / 10

Air Canada

7.0

Good

8,413 reviews

Copa Airlines

7.7

Good

1,712 reviews

Reviews

1 / 10

Frontier

6.1

Okay

3,472 reviews

Copa Airlines

7.7

Good

1,712 reviews

Reviews

1 / 10

Related info for your journey

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, Copa Airlines ($507), American Airlines ($517), and Frontier ($534) offers the cheapest pricing from Chicago to Port of Spain. Users have found that Copa Airlines is 19% 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

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Top 3 airlines flying from Chicago to Port of Spain

Airline	Cheapest	Average	Flexibility	On-time
Copa Airlines	Cheapest$430	Average$555	FlexibilityNo cancel fee	On-time70%
American Airlines	Cheapest$440	Average$672	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$480	Average$626	FlexibilityNo cancel fee	On-time69%

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$235+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Port of Spain with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Port of Spain

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chicago to Port of Spain

Cheapest flights from Chicago to Port of SpainExplore 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 December 22, 2024.

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 December 22, 2024.

Find flights from Chicago to Port of Spain within your budget

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 December.

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.

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?

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 December 22, 2024.

Rainfall in Port of Spain by month

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

Temperature in Port of Spain by month

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

Reviews of airlines servicing Port of Spain

Peruse reviews from past customers who have flown with American Airlines and United 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.

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?

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

Can I find deals for flights from Chicago to Port of Spain that include hotel bookings?

How can I find direct flights from Chicago to Port of Spain?

Can I find deals for business class flights from Chicago to Port of Spain?

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

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.

Top 3 airlines flying from Chicago to Port of Spain

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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 December 22, 2024.