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

Prices for flights from Port of Spain Piarco Intl Airport to Chicago were last updated today.

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

There is 1 operator available for flights from Port of Spain Piarco Intl Airport to Chicago as of September 2026.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Port of Spain Piarco Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$313 Cheap Flights from Port of Spain to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Port of Spain to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

13h 03m1 stop Toronto Pearson Intl

8:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 20m1 stop Toronto Pearson Intl

$615Air Canada

Fri, Oct 23 - Sat, Oct 31

1:20 am - 2:52 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 32m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

8:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 20m1 stop Toronto Pearson Intl

$619Air Canada

Fri, Oct 23 - Sat, Oct 31

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

30h 20m1 stop Fort Lauderdale

7:50 pm - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

46h 05m2 stops Atlanta Hartsfield-Jackson Miami

$642Multiple Airlines

Thu, Oct 22 - Thu, Oct 29

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

30h 20m1 stop Fort Lauderdale

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

11h 00m1 stop Fort Lauderdale

$659Multiple Airlines

Thu, Oct 22 - Thu, Oct 29

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

30h 20m1 stop Fort Lauderdale

8:04 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 56m1 stop Fort Lauderdale

$660Multiple Airlines

Fri, Oct 9 - Fri, Oct 23

10:10 am - 3:20 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 10m1 stop Fort Lauderdale

7:25 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

35h 35m2 stops Houston George Bush Intcntl Fort Lauderdale

$664Multiple Airlines

Fri, Sep 25 - Wed, Sep 30

1:20 am - 2:52 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 32m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

8:40 pm - 7:40 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

22h 00m2 stops Toronto Pearson Intl Bridgetown Grantley Adams Intl

$668Multiple Airlines

Wed, Oct 21 - Thu, Oct 29

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

22h 48m1 stop Panama City Tocumen Intl

2:13 pm - 1:55 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 42m1 stop Panama City Tocumen Intl

$678Copa Airlines

Wed, Dec 23 - Thu, Dec 31

3:06 pm - 12:33 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 27m1 stop Miami

7:29 pm - 2:08 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 39m1 stop Miami

$692American Airlines

Fri, Oct 2 - Mon, Oct 5

3:08 pm - 9:10 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

19h 02m2 stops Miami Charlotte Douglas

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

8h 03m1 stop Miami

$697American Airlines

Wed, Oct 21 - Sun, Oct 25

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Copa Airlines flights from Port of Spain to Chicago

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

Copa Airlines

Dec 23

POS3:23 amPort of Spain Piarco Intl

22h 48m

1 stop

ORD12:11 amChicago O'Hare Intl

Dec 31

ORD2:13 pmChicago O'Hare Intl

9h 42m

1 stop

POS1:55 amPort of Spain Piarco Intl

$678

Copa Airlines

Oct 20

POS3:50 amPort of Spain Piarco Intl

11h 09m

1 stop

ORD1:59 pmChicago O'Hare Intl

Oct 25

ORD3:13 pmChicago O'Hare Intl

21h 04m

1 stop

POS1:17 pmPort of Spain Piarco Intl

$680

American Airlines flights from Port of Spain to Chicago

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

American Airlines

Oct 2

POS3:06 pmPort of Spain Piarco Intl

10h 27m

1 stop

ORD12:33 amChicago O'Hare Intl

Oct 5

ORD7:29 pmChicago O'Hare Intl

17h 39m

1 stop

POS2:08 pmPort of Spain Piarco Intl

$692

American Airlines

Oct 2

POS3:06 pmPort of Spain Piarco Intl

19h 04m

2 stops

ORD9:10 amChicago O'Hare Intl

Oct 5

ORD9:29 pmChicago O'Hare Intl

15h 39m

2 stops

POS2:08 pmPort of Spain Piarco Intl

$697

American Airlines

Dec 24

POS6:05 amPort of Spain Piarco Intl

15h 54m

2 stops

ORD7:59 pmChicago O'Hare Intl

Dec 31

ORD8:35 amChicago O'Hare Intl

13h 10m

1 stop

POS11:45 pmPort of Spain Piarco Intl

$723

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Fri 10/23

1:20 am-1:23 pm

1 stop13h 03m

Chicago O'Hare Intl

Sat 10/31

8:40 pm-1:00 am

1 stop27h 20m

$615

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Fri 10/23

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Sat 10/31

8:40 pm-1:00 am

1 stop27h 20m

$619

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Thu 10/22

10:10 am-3:30 pm

1 stop30h 20m

Chicago O'Hare Intl

Thu 10/29

7:50 pm-6:55 pm

2 stops46h 05m

$642

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Thu 10/22

10:10 am-3:30 pm

1 stop30h 20m

Chicago O'Hare Intl

Thu 10/29

8:00 am-8:00 pm

1 stop11h 00m

$659

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Fri 10/9

10:10 am-3:30 pm

1 stop30h 20m

Chicago O'Hare Intl

Fri 10/23

8:04 am-8:00 pm

1 stop10h 56m

$660

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Fri 9/25

10:10 am-3:20 pm

1 stop30h 10m

Chicago O'Hare Intl

Wed 9/30

7:25 am-8:00 pm

2 stops35h 35m

$664

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Wed 10/21

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Thu 10/29

8:40 pm-7:40 pm

2 stops22h 00m

$668

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Wed 12/23

3:23 am-12:11 am

1 stop22h 48m

Chicago O'Hare Intl

Thu 12/31

2:13 pm-1:55 am

1 stop9h 42m

$678

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Fri 10/2

3:06 pm-12:33 am

1 stop10h 27m

Chicago O'Hare Intl

Mon 10/5

7:29 pm-2:08 pm

1 stop17h 39m

$692

Quickest round-trip

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Wed 10/21

3:08 pm-9:10 am

2 stops19h 02m

Chicago O'Hare Intl

Sun 10/25

5:05 am-2:08 pm

1 stop8h 03m

$697

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first

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

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

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

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

When to book flights from Port of Spain to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$313
Fastest flight time	11h 39m
Direct flights	None

The best one-way flight to Chicago from Port of Spain in the past 72 hours is $313. The best round-trip flight deal from Port of Spain to Chicago found on momondo in the last 72 hours is $615.

The fastest flight from Port of Spain to Chicago takes 11h 39m

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

Search flight deals

Frequently asked questions about flying from Port of Spain to Chicago

How far is Port of Spain Piarco Intl to Chicago by plane?
Port of Spain Piarco Intl and Chicago are 2671.5 mi apart from one another. A reasonable flight in good conditions will take 11h 39m.
When did momondo last update prices for flights from Port of Spain Piarco Intl Airport to Chicago?
Prices for flights from Port of Spain Piarco Intl Airport to Chicago were last updated today.
How many operators does momondo search for flights from Port of Spain Piarco Intl Airport to Chicago?
There is 1 operator available for flights from Port of Spain Piarco Intl Airport to Chicago as of September 2026.
How old do you have to be to fly from Port of Spain Piarco Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Port of Spain Piarco Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Port of Spain to Chicago

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

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $574	Free Cancellation	Rating 7.1 12,046 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from Port of Spain is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Port of Spain to Chicago flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Port of Spain and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Port of Spain to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Port of Spain to Chicago from $313

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Port of Spain to Chicago departing on 10/25. 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 Port of Spain to Chicago

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

American Airlines flights from Port of Spain to Chicago

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

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

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

When to book flights from Port of Spain to Chicago

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Port of Spain to Chicago

Best airlines flying from Port of Spain to Chicago

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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

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

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