What airlines fly to Trinidad and Tobago?

American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Trinidad and Tobago 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 Trinidad and Tobago. Keep in mind that there are 3 different airlines that fly to Trinidad and Tobago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Trinidad and Tobago?

Air Canada and American Airlines are the most popular carriers operating from Chicago to Trinidad and Tobago

When did momondo last update prices for flights from Chicago to Trinidad and Tobago?

Prices for flights from Chicago to Trinidad and Tobago are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago to Trinidad and Tobago?

As of August 2026, there are 3 operators available to choose from for flights from Chicago to Trinidad and Tobago.

How old do you have to be to fly from Chicago to Trinidad and Tobago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Trinidad and Tobago.

What documentation or ID do you need to fly to Trinidad and Tobago?

The required travel and health documents for your Trinidad and Tobago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Trinidad and Tobago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$223 Cheap Flights from Chicago to Trinidad and Tobago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Trinidad and Tobago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:11 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 49m1 stop Fort Lauderdale

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

30h 10m1 stop Fort Lauderdale

$484Multiple Airlines

Mon, Sep 14 - Mon, Sep 21

7:11 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 49m1 stop Fort Lauderdale

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

30h 10m1 stop Fort Lauderdale

$484Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

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

10h 56m1 stop Fort Lauderdale

10:10 am - 3:36 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 26m1 stop Fort Lauderdale

$499Multiple Airlines

Thu, Oct 8 - Mon, Oct 12

8:40 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

26h 35m1 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

$565Air Canada

Thu, Sep 10 - Sun, Sep 13

8:40 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

26h 35m1 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

$565Air Canada

Sun, Sep 13 - Mon, Sep 21

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 - 8:12 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

19h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$566Air Canada

Thu, Sep 10 - Sun, Sep 13

8:55 pm - 2:06 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 11m2 stops Washington, D.C. Reagan-National Miami

3:06 pm - 7:53 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 47m2 stops Miami New York LaGuardia

$621American Airlines

Tue, Sep 15 - Mon, Sep 21

5:00 am - 2:06 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

8h 06m1 stop Miami

3:06 pm - 7:53 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 47m2 stops Miami New York LaGuardia

$622American Airlines

Tue, Sep 15 - Mon, Sep 21

8:50 am - 11:23 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

13h 33m1 stop Houston George Bush Intcntl

12:30 am - 10:16 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 46m1 stop Houston George Bush Intcntl

$761United Airlines

Fri, Sep 18 - Wed, Sep 23

8:50 am - 11:23 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

13h 33m1 stop Houston George Bush Intcntl

12:30 am - 10:13 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 43m1 stop Houston George Bush Intcntl

$761United Airlines

Sat, Sep 19 - Thu, Sep 24

Cheap last minute flights

Enter your travel dates to find the best prices.

8:05 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 55m1 stop Fort Lauderdale

10:10 am - 12:50 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

27h 40m1 stop Fort Lauderdale

$645Multiple Airlines

Fri, Aug 21 - Mon, Aug 31

8:05 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 55m1 stop Fort Lauderdale

10:10 am - 12:50 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

27h 40m1 stop Fort Lauderdale

$658Multiple Airlines

Thu, Aug 20 - Mon, Aug 31

1:59 pm - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

29h 01m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

10:10 am - 12:50 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

27h 40m1 stop Fort Lauderdale

$678Multiple Airlines

Sat, Aug 22 - Mon, Aug 31

5:35 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

29h 40m1 stop Toronto Pearson Intl

1:25 am - 4:57 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 32m1 stop Toronto Pearson Intl

$739Air Canada

Sat, Aug 22 - Fri, Aug 28

8:50 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

26h 25m1 stop Toronto Pearson Intl

1:25 am - 6:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 21m2 stops Toronto Pearson Intl Ottawa

$744Air Canada

Sat, Aug 22 - Sun, Aug 30

9:50 am - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

13h 25m1 stop Toronto Pearson Intl

1:25 am - 2:55 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 30m1 stop Toronto Pearson Intl

$749Air Canada

Fri, Aug 21 - Fri, Aug 28

8:19 am - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

13h 59m2 stops Philadelphia Miami

7:00 am - 6:54 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 54m2 stops Miami Washington, D.C. Reagan-National

$808American Airlines

Fri, Aug 21 - Sun, Aug 30

5:00 am - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 18m1 stop Miami

7:00 am - 10:31 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 31m1 stop Miami

$826American Airlines

Sat, Aug 22 - Sat, Aug 29

8:50 am - 11:23 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

13h 33m1 stop Houston George Bush Intcntl

2:00 am - 11:59 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 59m1 stop Newark

$939United Airlines

Thu, Aug 20 - Fri, Aug 28

2:35 pm - 12:50 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 15m1 stop Newark

12:30 am - 12:48 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 18m1 stop Houston George Bush Intcntl

$966United Airlines

Sat, Aug 22 - Fri, Aug 28

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Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets

Air Canada

Sep 10

ORD8:40 pmChicago O'Hare Intl

26h 35m

1 stop

POS12:15 amPort of Spain Piarco Intl

Sep 13

POS1:20 amPort of Spain Piarco Intl

13h 03m

1 stop

ORD1:23 pmChicago O'Hare Intl

$565

Air Canada

Sep 10

ORD3:45 pmChicago O'Hare Intl

31h 30m

1 stop

POS12:15 amPort of Spain Piarco Intl

Sep 13

POS1:20 amPort of Spain Piarco Intl

19h 52m

2 stops

ORD8:12 pmChicago O'Hare Intl

$566

Air Canada

Sep 10

ORD8:40 pmChicago O'Hare Intl

26h 35m

1 stop

POS12:15 amPort of Spain Piarco Intl

Sep 13

POS1:20 amPort of Spain Piarco Intl

13h 03m

1 stop

ORD1:23 pmChicago O'Hare Intl

$568

American Airlines flights from Chicago to Trinidad and Tobago

Our best American Airlines deals on Chicago to Trinidad and Tobago flight tickets

American Airlines

Sep 15

ORD8:55 pmChicago O'Hare Intl

16h 11m

2 stops

POS2:06 pmPort of Spain Piarco Intl

Sep 21

POS3:06 pmPort of Spain Piarco Intl

17h 47m

2 stops

ORD7:53 amChicago O'Hare Intl

$621

American Airlines

Sep 15

ORD5:00 amChicago O'Hare Intl

8h 06m

1 stop

POS2:06 pmPort of Spain Piarco Intl

Sep 21

POS3:06 pmPort of Spain Piarco Intl

17h 47m

2 stops

ORD7:53 amChicago O'Hare Intl

$622

American Airlines

Sep 27

ORD9:01 pmChicago O'Hare Intl

16h 05m

2 stops

POS2:06 pmPort of Spain Piarco Intl

Oct 4

POS3:06 pmPort of Spain Piarco Intl

9h 24m

1 stop

ORD11:30 pmChicago O'Hare Intl

$627

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

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

Mon 9/14

7:11 am-8:00 pm

1 stop11h 49m

Port of Spain Piarco Intl

Mon 9/21

10:10 am-3:20 pm

1 stop30h 10m

$484

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 9/17

7:11 am-8:00 pm

1 stop11h 49m

Port of Spain Piarco Intl

Mon 9/21

10:10 am-3:20 pm

1 stop30h 10m

$484

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/8

8:04 am-8:00 pm

1 stop10h 56m

Port of Spain Piarco Intl

Mon 10/12

10:10 am-3:36 pm

1 stop30h 26m

$499

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 9/10

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 9/13

1:20 am-1:23 pm

1 stop13h 03m

$565

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sun 9/13

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Mon 9/21

1:20 am-1:23 pm

1 stop13h 03m

$565

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 9/10

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Sun 9/13

1:20 am-8:12 pm

2 stops19h 52m

$566

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 9/15

8:55 pm-2:06 pm

2 stops16h 11m

Port of Spain Piarco Intl

Mon 9/21

3:06 pm-7:53 am

2 stops17h 47m

$621

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 9/15

5:00 am-2:06 pm

1 stop8h 06m

Port of Spain Piarco Intl

Mon 9/21

3:06 pm-7:53 am

2 stops17h 47m

$622

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 9/18

8:50 am-11:23 pm

1 stop13h 33m

Port of Spain Piarco Intl

Wed 9/23

12:30 am-10:16 am

1 stop10h 46m

$761

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 9/19

8:50 am-11:23 pm

1 stop13h 33m

Port of Spain Piarco Intl

Thu 9/24

12:30 am-10:13 am

1 stop10h 43m

$761

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 Trinidad and Tobago

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

What is the cheapest month to fly to Trinidad and Tobago?

In general, November is the cheapest month to fly from Chicago to Trinidad and Tobago. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $443. If you aren’t able to travel to Trinidad and Tobago during the month of November, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $548.

Cheap Chicago to Trinidad and Tobago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Trinidad and Tobago

Best Price Found	$223
Fastest flight time	10h 56m
Direct flights	None

The best one-way flight to Trinidad and Tobago from Chicago in the past 72 hours is $223. The best round-trip flight deal from Chicago to Trinidad and Tobago found on momondo in the last 72 hours is $484.

The fastest flight from Chicago to Trinidad and Tobago takes 10h 56m

There are no direct flights from Chicago to Trinidad and Tobago. There are no popular flight routes from Chicago to Trinidad and Tobago.

Search flight deals

Frequently asked questions about flying from Chicago to Trinidad and Tobago

When did momondo last update prices for flights from Chicago to Trinidad and Tobago?
Prices for flights from Chicago to Trinidad and Tobago are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Trinidad and Tobago?
As of August 2026, there are 3 operators available to choose from for flights from Chicago to Trinidad and Tobago.
How old do you have to be to fly from Chicago to Trinidad and Tobago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Trinidad and Tobago.
What documentation or ID do you need to fly to Trinidad and Tobago?
The required travel and health documents for your Trinidad and Tobago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Trinidad and Tobago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Chicago to Trinidad and Tobago

Compare and see reviews for airlines that fly from Chicago to Trinidad and Tobago with momondo

Airline	Rating	Free Cancellation	Price
Copa Airlines	PriceFrom $285	Free Cancellation	Rating 7.6 1,557 reviews	Search Copa Airlines flights
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,488 reviews	Search Air Canada flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,952 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 10,104 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Trinidad and Tobago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Trinidad and Tobago from Chicago.

Can I find flights from Chicago to Trinidad and Tobago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Trinidad and Tobago flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Trinidad and Tobago?

Once all potential Chicago to Trinidad and Tobago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Trinidad and Tobago right now. Can momondo alert me if prices change?

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

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Popular cities in Trinidad and Tobago

Flights to Port of Spainfrom $275

Flights to Scarborough, Eastern Tobagofrom $396

Cheap flights from Chicago to Trinidad and Tobago from $223

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 Trinidad and Tobago departing on 10/5. 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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Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets

American Airlines flights from Chicago to Trinidad and Tobago

Our best American Airlines deals on Chicago to Trinidad and Tobago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

See travel insights to Trinidad and Tobago from

How to get the cheapest flight ticket from Chicago to Trinidad and Tobago

What is the cheapest month to fly to Trinidad and Tobago?

What is the cheapest airline that flies from Chicago to Trinidad and Tobago?

What airlines fly to Trinidad and Tobago?

Cheap Chicago to Trinidad and Tobago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago to Trinidad and Tobago

Best airlines flying from Chicago to Trinidad and Tobago

Compare and see reviews for airlines that fly from Chicago to Trinidad and Tobago with momondo

Why use momondo?

An easier way to manage your Trinidad and Tobago 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 Trinidad and Tobago

Popular cities in Trinidad and Tobago

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

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Fly your favorite airline to Trinidad and Tobago

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

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