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.

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

Air Canada, United Airlines, and American Airlines are the most popular carriers operating from Chicago to Port of Spain Piarco Intl

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.

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.

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 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.

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 October 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.

$324 Cheap Flights from Chicago to Port of Spain in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Port of Spain

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7:35 am - 1:55 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 20m1 stop Panama City Tocumen Intl

2:14 pm - 12:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

24h 32m1 stop Panama City Tocumen Intl

$648Copa Airlines

Tue, Jan 19 - Mon, Jan 25

7:35 am - 1:12 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 37m1 stop Panama City Tocumen Intl

3:36 am - 12:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 35m1 stop Panama City Tocumen Intl

$648Copa Airlines

Thu, Feb 18 - Sun, Feb 21

2:13 pm - 1:19 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

21h 06m1 stop Panama City Tocumen Intl

3:26 am - 12:07 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 41m1 stop Panama City Tocumen Intl

$648Copa Airlines

Sun, Jan 17 - Sun, Jan 24

7:50 pm - 3:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 45m1 stop Miami

4:42 pm - 9:30 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 48m1 stop Miami

$660American Airlines

Sat, Dec 5 - Sat, Dec 12

7:50 pm - 3:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 45m1 stop Miami

5:56 am - 5:24 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 28m2 stops Miami Washington, D.C. Reagan-National

$665American Airlines

Sat, Dec 5 - Sat, Dec 12

7:50 pm - 3:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 45m1 stop Miami

5:56 am - 8:11 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 15m2 stops Miami Charlotte Douglas

$665American Airlines

Sat, Dec 5 - Sat, Dec 12

12:30 pm - 11:20 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 50m1 stop Houston George Bush Intcntl

12:30 am - 9:25 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

9h 55m1 stop Houston George Bush Intcntl

$680United Airlines

Sat, Mar 27 - Thu, Apr 1

10:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 55m1 stop Toronto Pearson Intl

2:15 am - 1:13 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 58m1 stop Toronto Pearson Intl

$694Air Canada

Thu, Dec 3 - Fri, Dec 11

10:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 55m1 stop Toronto Pearson Intl

2:15 am - 1:13 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 58m1 stop Toronto Pearson Intl

$696Air Canada

Thu, Dec 3 - Thu, Dec 10

9:21 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 57m1 stop Houston George Bush Intcntl

1:25 am - 11:15 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 50m1 stop Houston George Bush Intcntl

$790United Airlines

Thu, Dec 3 - Tue, Dec 8

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12:40 pm - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 38m1 stop Houston George Bush Intcntl

1:25 am - 2:51 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 26m1 stop Houston George Bush Intcntl

$807United Airlines

Thu, Oct 29 - Mon, Nov 9

7:29 am - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 49m1 stop Houston George Bush Intcntl

1:25 am - 10:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 46m1 stop Houston George Bush Intcntl

$807United Airlines

Thu, Oct 29 - Wed, Nov 4

10:34 am - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 44m1 stop Houston George Bush Intcntl

1:25 am - 11:17 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 52m1 stop Houston George Bush Intcntl

$917United Airlines

Fri, Oct 30 - Thu, Nov 5

5:15 pm - 7:30 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

25h 15m2 stops Las Vegas Harry Reid Intl Orlando

9:10 am - 3:31 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

32h 21m3 stops Miami Atlanta Hartsfield-Jackson Dallas/Fort Worth

$921Multiple Airlines

Thu, Oct 29 - Tue, Nov 10

8:00 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 00m1 stop Fort Lauderdale

9:10 am - 6:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

35h 20m2 stops Miami Atlanta Hartsfield-Jackson

$953Multiple Airlines

Thu, Oct 29 - Tue, Nov 10

5:15 pm - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

24h 40m3 stops Las Vegas Harry Reid Intl Atlanta Hartsfield-Jackson Miami

9:10 am - 3:31 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

32h 21m3 stops Miami Atlanta Hartsfield-Jackson Dallas/Fort Worth

$967Multiple Airlines

Thu, Oct 29 - Tue, Nov 10

5:15 pm - 7:30 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

25h 15m2 stops Las Vegas Harry Reid Intl Orlando

9:50 am - 3:38 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

31h 48m2 stops Willemstad Hato Int. Toronto Pearson Intl

$990Multiple Airlines

Thu, Oct 29 - Tue, Nov 10

5:15 pm - 7:30 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

25h 15m2 stops Las Vegas Harry Reid Intl Orlando

9:00 am - 7:58 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

36h 58m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl

$994Multiple Airlines

Thu, Oct 29 - Thu, Nov 5

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

8h 03m1 stop Miami

4:42 pm - 7:26 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 44m2 stops Miami Washington, D.C. Reagan-National

$1,024American Airlines

Thu, Oct 29 - Thu, Nov 5

5:15 pm - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

24h 40m3 stops Las Vegas Harry Reid Intl Atlanta Hartsfield-Jackson Miami

9:00 am - 3:52 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

32h 52m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl

$1,044Multiple Airlines

Thu, Oct 29 - Thu, Nov 5

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Copa Airlines flights from Chicago to Port of Spain

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

Copa Airlines

Jan 5

ORD12:27 amChicago O'Hare Intl

23h 28m

1 stop

POS1:55 amPort of Spain Piarco Intl

Jan 18

POS2:14 pmPort of Spain Piarco Intl

11h 53m

1 stop

ORD12:07 amChicago O'Hare Intl

$648

Copa Airlines

Dec 3

ORD7:35 amChicago O'Hare Intl

27h 52m

1 stop

POS1:27 pmPort of Spain Piarco Intl

Dec 8

POS3:23 amPort of Spain Piarco Intl

11h 23m

1 stop

ORD12:46 pmChicago O'Hare Intl

$795

Copa Airlines

Oct 30

ORD3:13 pmChicago O'Hare Intl

9h 41m

1 stop

POS1:54 amPort of Spain Piarco Intl

Nov 4

POS3:40 amPort of Spain Piarco Intl

22h 31m

1 stop

ORD12:11 amChicago O'Hare Intl

$830

American Airlines flights from Chicago to Port of Spain

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

American Airlines

Dec 5

ORD7:50 pmChicago O'Hare Intl

17h 45m

1 stop

POS3:35 pmPort of Spain Piarco Intl

Dec 12

POS4:42 pmPort of Spain Piarco Intl

18h 48m

1 stop

ORD9:30 amChicago O'Hare Intl

$660

American Airlines

Dec 5

ORD7:50 pmChicago O'Hare Intl

17h 45m

1 stop

POS3:35 pmPort of Spain Piarco Intl

Dec 12

POS5:56 amPort of Spain Piarco Intl

16h 15m

2 stops

ORD8:11 pmChicago O'Hare Intl

$665

American Airlines

Jan 15

ORD9:29 pmChicago O'Hare Intl

16h 14m

2 stops

POS3:43 pmPort of Spain Piarco Intl

Jan 24

POS4:43 pmPort of Spain Piarco Intl

20h 20m

2 stops

ORD11:03 amChicago O'Hare Intl

$670

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

Tue 1/19

7:35 am-1:55 am

1 stop16h 20m

Port of Spain Piarco Intl

Mon 1/25

2:14 pm-12:46 pm

1 stop24h 32m

$648

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 2/18

7:35 am-1:12 pm

1 stop27h 37m

Port of Spain Piarco Intl

Sun 2/21

3:36 am-12:11 am

1 stop22h 35m

$648

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sun 1/17

2:13 pm-1:19 pm

1 stop21h 06m

Port of Spain Piarco Intl

Sun 1/24

3:26 am-12:07 am

1 stop22h 41m

$648

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 12/5

7:50 pm-3:35 pm

1 stop17h 45m

Port of Spain Piarco Intl

Sat 12/12

4:42 pm-9:30 am

1 stop18h 48m

$660

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 12/5

7:50 pm-3:35 pm

1 stop17h 45m

Port of Spain Piarco Intl

Sat 12/12

5:56 am-5:24 pm

2 stops13h 28m

$665

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 12/5

7:50 pm-3:35 pm

1 stop17h 45m

Port of Spain Piarco Intl

Sat 12/12

5:56 am-8:11 pm

2 stops16h 15m

$665

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 3/27

12:30 pm-11:20 pm

1 stop9h 50m

Port of Spain Piarco Intl

Thu 4/1

12:30 am-9:25 am

1 stop9h 55m

$680

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 12/3

10:05 am-1:00 am

1 stop12h 55m

Port of Spain Piarco Intl

Fri 12/11

2:15 am-1:13 pm

1 stop12h 58m

$694

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 12/3

10:05 am-1:00 am

1 stop12h 55m

Port of Spain Piarco Intl

Thu 12/10

2:15 am-1:13 pm

1 stop12h 58m

$696

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 12/3

9:21 am-12:18 am

1 stop12h 57m

Port of Spain Piarco Intl

Tue 12/8

1:25 am-11:15 am

1 stop11h 50m

$790

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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 $623. If you’re not able to fly to Port of Spain in November, then July is your next best option. Flight prices from Chicago to Port of Spain during July average around $629.

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	$324
Fastest flight time	11h 50m
Direct flights	None

The best one-way flight to Port of Spain from Chicago in the past 72 hours is $324. The best round-trip flight deal from Chicago to Port of Spain found on momondo in the last 72 hours is $648.

The fastest flight from Chicago to Port of Spain takes 11h 50m

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

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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. 11h 50m 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 October 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 American Airlines, making up 52% of the total bookings. Other popular airlines include Air Canada with 48%.

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 11,815 reviews	Search Air Canada flights
United Airlines	PriceFrom $578	Free Cancellation	Rating 7.3 10,439 reviews	Search United Airlines flights
American Airlines	PriceFrom $623	Free Cancellation	Rating 7.0 12,194 reviews	Search American Airlines flights

Piarco

Why use momondo?

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 $324

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 12/1. 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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Copa Airlines flights from Chicago to Port of Spain

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

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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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

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

Traveling to a place near Port of Spain?

Why use momondo?

An easier way to manage your Port of Spain trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Airports servicing Trinidad and Tobago

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Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Port of Spain

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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