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 43% of people opting to fly with this airline when traveling to Trinidad and Tobago. Keep in mind that there are 4 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 4 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 - 2:45 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

29h 35m1 stop Fort Lauderdale

$490Multiple Airlines

Thu, Sep 24 - Thu, Oct 1

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

11h 49m1 stop Fort Lauderdale

10:10 am - 2:45 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

29h 35m1 stop Fort Lauderdale

$494Multiple Airlines

Thu, Sep 24 - Thu, Oct 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 - 3:38 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 23m1 stop Toronto Pearson Intl

$517Air Canada

Fri, Jan 8 - Sun, Jan 10

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 - 11:07 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

34h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$521Air Canada

Fri, Jan 8 - Sun, Jan 10

8:01 am - 1:47 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 46m1 stop Panama City Tocumen Intl

3:50 am - 1:59 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 09m1 stop Panama City Tocumen Intl

$568Copa Airlines

Wed, Sep 23 - Sat, Sep 26

8:01 am - 1:47 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 46m1 stop Panama City Tocumen Intl

2:23 pm - 1:59 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

24h 36m1 stop Panama City Tocumen Intl

$568Copa Airlines

Tue, Sep 22 - Sat, Sep 26

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

19h 04m2 stops Miami Washington, D.C. Reagan-National

$584American Airlines

Tue, Sep 22 - Sat, Sep 26

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

10h 27m1 stop Miami

$584American Airlines

Tue, Sep 22 - Sat, Sep 26

10:42 am - 12:23 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 41m1 stop Houston George Bush Intcntl

2:20 am - 10:47 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 27m1 stop Newark

$630United Airlines

Sat, Jan 23 - Sat, Jan 30

6:50 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

15h 28m1 stop Houston George Bush Intcntl

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

23h 45m1 stop Houston George Bush Intcntl

$846United Airlines

Mon, Dec 28 - Tue, Dec 29

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Copa Airlines flights from Chicago to Trinidad and Tobago

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

Copa Airlines

Sep 22

ORD8:01 amChicago O'Hare Intl

16h 46m

1 stop

POS1:47 amPort of Spain Piarco Intl

Sep 26

POS2:23 pmPort of Spain Piarco Intl

24h 36m

1 stop

ORD1:59 pmChicago O'Hare Intl

$568

Copa Airlines

Sep 27

ORD3:20 pmChicago O'Hare Intl

20h 57m

1 stop

POS1:17 pmPort of Spain Piarco Intl

Oct 3

POS3:50 amPort of Spain Piarco Intl

11h 09m

1 stop

ORD1:59 pmChicago O'Hare Intl

$662

Copa Airlines

Sep 27

ORD3:20 pmChicago O'Hare Intl

20h 57m

1 stop

POS1:17 pmPort of Spain Piarco Intl

Oct 3

POS3:50 amPort of Spain Piarco Intl

11h 09m

1 stop

ORD1:59 pmChicago O'Hare Intl

$665

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 22

ORD8:55 pmChicago O'Hare Intl

16h 11m

2 stops

POS2:06 pmPort of Spain Piarco Intl

Sep 26

POS3:06 pmPort of Spain Piarco Intl

10h 27m

1 stop

ORD12:33 amChicago O'Hare Intl

$584

American Airlines

Sep 23

ORD9:01 pmChicago O'Hare Intl

16h 05m

2 stops

POS2:06 pmPort of Spain Piarco Intl

Sep 27

POS3:06 pmPort of Spain Piarco Intl

17h 47m

2 stops

ORD7:53 amChicago O'Hare Intl

$594

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

Thu 9/24

7:11 am-8:00 pm

1 stop11h 49m

Port of Spain Piarco Intl

Thu 10/1

10:10 am-2:45 pm

1 stop29h 35m

$490

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 9/24

7:11 am-8:00 pm

1 stop11h 49m

Port of Spain Piarco Intl

Thu 10/1

10:10 am-2:45 pm

1 stop29h 35m

$494

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 1/8

10:05 am-1:00 am

1 stop12h 55m

Port of Spain Piarco Intl

Sun 1/10

2:15 am-3:38 pm

1 stop15h 23m

$517

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 1/8

12:50 pm-1:00 am

1 stop10h 10m

Port of Spain Piarco Intl

Sun 1/10

2:15 am-11:07 am

2 stops34h 52m

$521

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Wed 9/23

8:01 am-1:47 am

1 stop16h 46m

Port of Spain Piarco Intl

Sat 9/26

3:50 am-1:59 pm

1 stop11h 09m

$568

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 9/22

8:01 am-1:47 am

1 stop16h 46m

Port of Spain Piarco Intl

Sat 9/26

2:23 pm-1:59 pm

1 stop24h 36m

$568

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 9/22

8:55 pm-2:06 pm

2 stops16h 11m

Port of Spain Piarco Intl

Sat 9/26

3:06 pm-9:10 am

2 stops19h 04m

$584

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 9/22

8:55 pm-2:06 pm

2 stops16h 11m

Port of Spain Piarco Intl

Sat 9/26

3:06 pm-12:33 am

1 stop10h 27m

$584

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 1/23

10:42 am-12:23 am

1 stop11h 41m

Port of Spain Piarco Intl

Sat 1/30

2:20 am-10:47 am

1 stop10h 27m

$630

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Mon 12/28

6:50 am-12:18 am

1 stop15h 28m

Port of Spain Piarco Intl

Tue 12/29

1:25 am-11:10 pm

1 stop23h 45m

$846

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 March is also cheap. Prices for this month can be found on momondo for an average of $593.

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

Fastest flight time	10h 55m
Direct flights	None

The fastest flight from Chicago to Trinidad and Tobago takes 10h 55m

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 4 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 1,560 reviews	Search Copa Airlines flights
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,471 reviews	Search Air Canada flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,935 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 10,109 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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Flights to Port of Spainfrom $304

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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Copa Airlines flights from Chicago to Trinidad and Tobago

Our best Copa Airlines 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

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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

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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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