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

According to our current data, United Airlines ($480), and American Airlines ($487) offers the cheapest pricing from Chicago to Port of Spain. Users have found that United Airlines is 33% 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.

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.

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).

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 February. Prices are generally better when you fly from Chicago to Port of Spain in January, with the cheapest ticket starting at $477.

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.

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.

$191+ Cheap Flights from Chicago to Port of Spain

Q: How much does it cost to fly round-trip from Chicago to Port of Spain?

Airfare is below average for this route at the moment. Chicago to Port of Spain flights typically cost between $632 and $691 in September. The cheapest round-trip price found within the last 3 days was $441 on Multiple Airlines (Sep 17-Sep 21).

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Cheap flight deals from Chicago to Port of Spain

Round-trip from	$441 (Kiwi.com)
One-way from	$191 (Kiwi.com)
Popular in	February
Cheapest in	January
Average price	$711

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. 17% potential increase in price ($152 potential increase over avg. RT price).

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Cheapest flight prices on average. 9% potential price decrease ($63 potential savings vs. average RT price).

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Average for round-trip flights in August 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 August 26, 2025.

Wed 9/176:44 pmORD - POS

1 stop24h 16mMultiple Airlines

Sun 9/216:25 pmPOS - ORD

1 stop15h 53mMultiple Airlines

Deal found 8/26

$441

Wed 10/2210:27 amORD - POS

2 stops38h 19mMultiple Airlines

Sun 10/2610:10 amPOS - ORD

1 stop9h 26mMultiple Airlines

Deal found 8/25

$482

Wed 9/1011:57 amORD - POS

2 stops12h 49mMultiple Airlines

Tue 9/239:10 amPOS - ORD

1 stop25h 08mMultiple Airlines

Deal found 8/25

$504

Sat 11/228:15 pmORD - POS

1 stop26h 55mAir Canada

Fri 11/282:15 amPOS - ORD

1 stop12h 46mAir Canada

Deal found 8/24

$523

Wed 9/106:06 pmORD - POS

2 stops54h 14mAir Canada

Mon 9/222:25 amPOS - ORD

1 stop13h 39mAir Canada

Deal found 8/25

$533

Fri 9/52:00 pmORD - POS

1 stop10h 20mMultiple Airlines

Thu 9/256:25 pmPOS - ORD

1 stop15h 53mMultiple Airlines

Deal found 8/24

$538

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 August 26, 2025.

Wed 9/176:44 pmORD - POS

1 stop24h 16mMultiple Airlines

Sun 9/216:25 pmPOS - ORD

1 stop15h 53mMultiple Airlines

Deal found 8/26

$441

Sat 11/228:15 pmORD - POS

1 stop26h 55mAir Canada

Fri 11/282:15 amPOS - ORD

1 stop12h 46mAir Canada

Deal found 8/24

$523

Wed 10/2210:27 amORD - POS

2 stops38h 19mMultiple Airlines

Sun 10/2610:10 amPOS - ORD

1 stop9h 26mMultiple Airlines

Deal found 8/25

$482

Wed 9/1011:57 amORD - POS

2 stops12h 49mMultiple Airlines

Tue 9/239:10 amPOS - ORD

1 stop25h 08mMultiple Airlines

Deal found 8/25

$504

Last-minute flights from Chicago to Port of Spain
Discover last-minute flight deals from Chicago to Port of Spain. Data last updated August 26, 2025 and is based on user searches.

Wed 9/312:45 pmORD - POS

1 stop9h 38mUnited Airlines

Sun 9/712:30 amPOS - ORD

1 stop20h 28mUnited Airlines

Deal found 8/25

$549

Fri 9/52:00 pmORD - POS

1 stop10h 20mMultiple Airlines

Thu 9/256:25 pmPOS - ORD

1 stop15h 53mMultiple Airlines

Deal found 8/24

$538

Fri 9/58:30 pmORD - POS

2 stops16h 46mAmerican Airlines

Thu 9/253:25 pmPOS - ORD

2 stops16h 59mAmerican Airlines

Deal found 8/24

$553

Wed 9/1011:57 amORD - POS

2 stops12h 49mMultiple Airlines

Tue 9/239:10 amPOS - ORD

1 stop25h 08mMultiple Airlines

Deal found 8/25

$504

Wed 9/106:06 pmORD - POS

2 stops54h 14mAir Canada

Mon 9/222:25 amPOS - ORD

1 stop13h 39mAir Canada

Deal found 8/25

$533

Wed 9/176:44 pmORD - POS

1 stop24h 16mMultiple Airlines

Sun 9/216:25 pmPOS - ORD

1 stop15h 53mMultiple Airlines

Deal found 8/26

$441

Wed 9/177:00 amORD - POS

1 stop15h 23mUnited Airlines

Sat 9/2012:30 amPOS - ORD

1 stop10h 43mUnited Airlines

Deal found 8/26

$548

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 August 26, 2025.

Wed 9/176:44 pmORD - POS

1 stop24h 16mMultiple Airlines

Deal found 8/24

$191

Wed 9/106:44 pmORD - POS

1 stop24h 16mMultiple Airlines

Deal found 8/25

$209

Thu 9/115:05 amORD - POS

1 stop13h 55mMultiple Airlines

Deal found 8/25

$215

Wed 9/37:00 amORD - POS

1 stop15h 23mUnited Airlines

Deal found 8/25

$251

Tue 12/168:41 amORD - POS

2 stops26h 36mMultiple Airlines

Deal found 8/24

$294

Tue 12/231:35 pmORD - POS

2 stops21h 42mMultiple Airlines

Deal found 8/24

$347

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/17

6:44 pm-8:00 pm

1 stop24h 16m

Port of Spain Piarco Intl

Sun 9/21

6:25 pm-9:18 am

1 stop15h 53m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

10:27 am-1:46 am

2 stops38h 19m

Port of Spain Piarco Intl

Sun 10/26

10:10 am-6:36 pm

1 stop9h 26m

$482

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/10

11:57 am-1:46 am

2 stops12h 49m

Port of Spain Piarco Intl

Tue 9/23

9:10 am-9:18 am

1 stop25h 08m

$504

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

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/17

6:44 pm-8:00 pm

1 stop24h 16m

$191

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/10

6:44 pm-8:00 pm

1 stop24h 16m

$209

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/11

5:05 am-8:00 pm

1 stop13h 55m

$215

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/3

7:00 am-11:23 pm

1 stop15h 23m

$251

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/16

8:41 am-1:17 pm

2 stops26h 36m

$294

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/23

1:35 pm-1:17 pm

2 stops21h 42m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

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?

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.

How much does it cost to fly round-trip from Chicago to Port of Spain?

Reviews of airlines servicing Port of Spain

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

8,943 reviews

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

8,943 reviews

United Airlines

7.4

Good

8,943 reviews

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

8,943 reviews

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

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, United Airlines ($480), and American Airlines ($487) offers the cheapest pricing from Chicago to Port of Spain. Users have found that United Airlines is 33% 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 2 airlines flying from Chicago to Port of Spain

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$480	Average$626	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$487	Average$610	FlexibilityNo cancel fee	On-time71%

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$191+ 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 9/17. 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

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Port of Spain

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 August 26, 2025.

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 August 26, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Port of Spain that are best for you.

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.

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?

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 August 26, 2025.

How much does it cost to fly round-trip from Chicago to Port of Spain?

Reviews of airlines servicing Port of Spain

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.

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 2 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 August 26, 2025.