What airlines fly to Port of Spain?

American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Port of Spain from Chicago according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Port of Spain. Keep in mind that there are 3 different airlines that fly to Port of Spain on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Port of Spain Piarco Intl?

Air Canada is the most popular carrier operating from Chicago to Port of Spain Piarco Intl

Which layover airport has the shortest connection time from Chicago to Port of Spain?

Miami (MIA) has the shortest average layover time for this route: 1h 55m.

Which layover airport has the shortest travel time from Chicago to Port of Spain?

Flights connecting via Miami (MIA) have the shortest average one-way travel time: 8h 11m.

Which airport is the most popular layover for flights between Chicago and Port of Spain?

Panama City (PTY) was the most common stop: 38% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Port of Spain?

Flights via Toronto (YYZ) offer the lowest average round-trip price of $507.

When did momondo last update prices for flights from Chicago to Port of Spain Piarco Intl Airport?

Prices for flights from Chicago to Port of Spain Piarco Intl Airport refresh daily.

How many operators does momondo search for flights from Chicago to Port of Spain Piarco Intl Airport?

As of August 2026, there are 3 operators available to choose from for flights from Chicago to Port of Spain Piarco Intl Airport.

How old do you have to be to fly from Chicago to Port of Spain Piarco Intl Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Port of Spain Piarco Intl Airport.

What documentation or ID do you need to fly to Port of Spain Piarco Intl Airport?

The travel and health documents required for your trip to Port of Spain Piarco Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Port of Spain Piarco Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$241 Cheap Flights from Chicago to Port of Spain in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Port of Spain

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One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:50 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 10m1 stop Toronto Pearson Intl

2:15 am - 3:38 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 23m1 stop Toronto Pearson Intl

$527Air Canada

Thu, Nov 26 - Sun, Nov 29

2:15 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 00m1 stop Toronto Pearson Intl

1:20 am - 1:23 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 03m1 stop Toronto Pearson Intl

$527Air Canada

Mon, Oct 12 - Sun, Oct 18

3:45 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

31h 30m1 stop Toronto Pearson Intl

1:20 am - 2:55 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 35m1 stop Toronto Pearson Intl

$529Air Canada

Sat, Sep 12 - Sun, Sep 20

6:00 am - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 55m2 stops Baltimore/Washington Miami

10:10 am - 3:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 20m1 stop Fort Lauderdale

$599Multiple Airlines

Mon, Oct 12 - Mon, Oct 19

7:35 am - 1:27 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 52m1 stop Panama City Tocumen Intl

3:23 am - 12:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 48m1 stop Panama City Tocumen Intl

$618Copa Airlines

Thu, Dec 3 - Tue, Dec 8

8:35 am - 1:54 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 19m1 stop Panama City Tocumen Intl

3:40 am - 12:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 06m1 stop Panama City Tocumen Intl

$618Copa Airlines

Wed, Oct 28 - Sun, Nov 1

5:05 am - 2:08 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

8h 03m1 stop Miami

3:08 pm - 11:33 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

9h 25m1 stop Miami

$626American Airlines

Sun, Oct 11 - Sun, Oct 18

5:05 am - 2:08 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

8h 03m1 stop Miami

3:08 pm - 7:27 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 19m2 stops Miami Washington, D.C. Reagan-National

$626American Airlines

Sun, Oct 11 - Sun, Oct 18

10:32 am - 11:23 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 51m1 stop Houston George Bush Intcntl

12:30 am - 12:25 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 55m1 stop Houston George Bush Intcntl

$630United Airlines

Wed, Oct 7 - Tue, Oct 13

10:32 am - 11:23 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 51m1 stop Houston George Bush Intcntl

12:30 am - 11:16 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 46m1 stop Houston George Bush Intcntl

$630United Airlines

Sun, Sep 27 - Sat, Oct 3

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American Airlines flights from Chicago to Port of Spain

Our best American Airlines deals on Chicago to Port of Spain flight tickets

American Airlines

Oct 11

ORD5:05 amChicago O'Hare Intl

8h 03m

1 stop

POS2:08 pmPort of Spain Piarco Intl

Oct 18

POS3:08 pmPort of Spain Piarco Intl

17h 19m

2 stops

ORD7:27 amChicago O'Hare Intl

$626

American Airlines

Dec 3

ORD7:54 amChicago O'Hare Intl

13h 41m

2 stops

POS11:35 pmPort of Spain Piarco Intl

Dec 11

POS6:00 amPort of Spain Piarco Intl

13h 37m

2 stops

ORD5:37 pmChicago O'Hare Intl

$634

American Airlines

Oct 11

ORD7:29 pmChicago O'Hare Intl

17h 39m

1 stop

POS2:08 pmPort of Spain Piarco Intl

Oct 18

POS3:08 pmPort of Spain Piarco Intl

10h 30m

1 stop

ORD12:38 amChicago O'Hare Intl

$635

Air Canada flights from Chicago to Port of Spain

Our best Air Canada deals on Chicago to Port of Spain flight tickets

Air Canada

Oct 12

ORD2:15 pmChicago O'Hare Intl

9h 00m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 18

POS1:20 amPort of Spain Piarco Intl

13h 03m

1 stop

ORD1:23 pmChicago O'Hare Intl

$527

Air Canada

Sep 12

ORD3:45 pmChicago O'Hare Intl

31h 30m

1 stop

POS12:15 amPort of Spain Piarco Intl

Sep 20

POS1:20 amPort of Spain Piarco Intl

14h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$529

Air Canada

Oct 12

ORD2:15 pmChicago O'Hare Intl

9h 00m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 18

POS1:20 amPort of Spain Piarco Intl

14h 32m

2 stops

ORD2:52 pmChicago O'Hare Intl

$531

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Thu 11/26

12:50 pm-1:00 am

1 stop10h 10m

Port of Spain Piarco Intl

Sun 11/29

2:15 am-3:38 pm

1 stop15h 23m

$527

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Mon 10/12

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Sun 10/18

1:20 am-1:23 pm

1 stop13h 03m

$527

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Sat 9/12

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Sun 9/20

1:20 am-2:55 pm

1 stop14h 35m

$529

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Mon 10/12

6:00 am-6:55 pm

2 stops11h 55m

Port of Spain Piarco Intl

Mon 10/19

10:10 am-3:30 pm

1 stop30h 20m

$599

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Thu 12/3

7:35 am-1:27 pm

1 stop27h 52m

Port of Spain Piarco Intl

Tue 12/8

3:23 am-12:11 am

1 stop22h 48m

$618

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Wed 10/28

8:35 am-1:54 am

1 stop16h 19m

Port of Spain Piarco Intl

Sun 11/1

3:40 am-12:46 pm

1 stop11h 06m

$618

Quickest round-trip

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Sun 10/11

5:05 am-2:08 pm

1 stop8h 03m

Port of Spain Piarco Intl

Sun 10/18

3:08 pm-11:33 pm

1 stop9h 25m

$626

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Sun 10/11

5:05 am-2:08 pm

1 stop8h 03m

Port of Spain Piarco Intl

Sun 10/18

3:08 pm-7:27 am

2 stops17h 19m

$626

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Wed 10/7

10:32 am-11:23 pm

1 stop11h 51m

Port of Spain Piarco Intl

Tue 10/13

12:30 am-12:25 pm

1 stop12h 55m

$630

ChicagoPort of Spain

ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl

ORDPOS

Chicago O'Hare Intl

Sun 9/27

10:32 am-11:23 pm

1 stop11h 51m

Port of Spain Piarco Intl

Sat 10/3

12:30 am-11:16 am

1 stop11h 46m

$630

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Port of Spain

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

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

The month of November is, on average, the cheapest month to fly to Port of Spain from Chicago, with most prices found around $443. If you’re not able to fly to Port of Spain in November, then October is your next best option. Flight prices from Chicago to Port of Spain during October average around $548.

When to book flights from Chicago to Port of Spain

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Port of Spain according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Port of Spain (CHI to POS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Port of Spain

Best Price Found	$241
Fastest flight time	10h 10m
Direct flights	None

The best one-way flight to Port of Spain from Chicago in the past 72 hours is $241. The best round-trip flight deal from Chicago to Port of Spain found on momondo in the last 72 hours is $527.

The fastest flight from Chicago to Port of Spain takes 10h 10m

There are no direct flights from Chicago to Port of Spain. There are no popular flight routes from Chicago to Port of Spain.

Search flight deals

Frequently asked questions about flying from Chicago to Port of Spain

How far is Chicago to Port of Spain Piarco Intl by plane?
Port of Spain Piarco Intl is 2671.5 mi away from Chicago. 10h 10m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Port of Spain Piarco Intl Airport?
Prices for flights from Chicago to Port of Spain Piarco Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to Port of Spain Piarco Intl Airport?
As of August 2026, there are 3 operators available to choose from for flights from Chicago to Port of Spain Piarco Intl Airport.
How old do you have to be to fly from Chicago to Port of Spain Piarco Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Port of Spain Piarco Intl Airport.
What documentation or ID do you need to fly to Port of Spain Piarco Intl Airport?
The travel and health documents required for your trip to Port of Spain Piarco Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Port of Spain Piarco Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Chicago to Port of Spain?
Based on momondo bookings for flights between Chicago and Port of Spain, the leading airline is Air Canada, making up 100% of the total bookings.

Best airlines flying from Chicago to Port of Spain

Compare and see reviews for airlines that fly from Chicago to Port of Spain with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,555 reviews	Search Air Canada flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 12,022 reviews	Search American Airlines flights
United Airlines	PriceFrom $578	Free Cancellation	Rating 7.4 10,138 reviews	Search United Airlines flights

Piarco

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Why should I use momondo to find a flight deal from Chicago to Port of Spain?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Port of Spain. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Port of Spain with flexible booking policies on momondo?

Flights from Chicago to Port of Spain with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Port of Spain?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Port of Spain from Chicago.

I’m not ready to book a flight from Chicago to Port of Spain right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Port of Spain, momondo offers a useful price alert feature which will track prices for flights to Port of Spain from Chicago and alert you when they change.

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Cheap flights from Chicago to Port of Spain from $241

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 10/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Chicago to Port of Spain

Our best American Airlines deals on Chicago to Port of Spain flight tickets

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How to get the cheapest flight ticket from Chicago to Port of Spain

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

What is the cheapest airline that flies from Chicago to Port of Spain Piarco Intl?

What airlines fly to Port of Spain?

Which airport is the most popular layover for flights between Chicago and Port of Spain?

Which layover airport offers the lowest fares from Chicago to Port of Spain?

Which layover airport has the shortest travel time from Chicago to Port of Spain?

Which layover airport has the shortest connection time from Chicago to Port of Spain?

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Cheap Chicago to Port of Spain (CHI to POS) flight deals and tips

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Frequently asked questions about flying from Chicago to Port of Spain

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Compare and see reviews for airlines that fly from Chicago to Port of Spain with momondo

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An easier way to manage your Port of Spain trip

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List of cabin classes available on flights landing in Port of Spain. Availability may vary depending on flight origin and airline.

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