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 44% 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 United 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 July 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.

$219 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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 6:20 pm

ORD

POS

11h 20m

1 stop

8:00 pm - 8:43 am

POS

ORD

13h 43m

1 stop

$456JetBlue

Sat, Aug 22 - Mon, Aug 31

9:50 am - 12:15 am

ORD

POS

13h 25m

1 stop

1:20 am - 4:58 pm

POS

ORD

16h 38m

1 stop

$485Air Canada

Mon, Sep 28 - Fri, Oct 2

2:15 pm - 12:15 am

ORD

POS

9h 00m

1 stop

1:20 am - 2:52 pm

POS

ORD

14h 32m

2 stops

$488Air Canada

Mon, Sep 28 - Fri, Oct 2

8:45 am - 12:15 am

ORD

POS

14h 30m

2 stops

1:20 am - 2:52 pm

POS

ORD

14h 32m

2 stops

$492Air Canada

Mon, Sep 28 - Fri, Oct 2

6:00 am - 6:20 pm

ORD

POS

11h 20m

1 stop

8:00 pm - 8:43 am

POS

ORD

13h 43m

1 stop

$497JetBlue

Sat, Aug 22 - Mon, Aug 31

8:40 pm - 12:15 am

ORD

POS

26h 35m

1 stop

1:25 am - 1:22 pm

POS

ORD

12h 57m

1 stop

$533Air Canada

Tue, Aug 11 - Mon, Aug 17

8:40 pm - 12:15 am

ORD

POS

26h 35m

1 stop

1:25 am - 2:44 pm

POS

ORD

14h 19m

2 stops

$536Air Canada

Tue, Aug 11 - Mon, Aug 17

6:30 pm - 1:44 pm

ORD

POS

18h 14m

1 stop

8:00 pm - 8:46 am

POS

ORD

13h 46m

1 stop

$540JetBlue

Wed, Aug 19 - Wed, Aug 26

6:21 pm - 12:15 am

ORD

POS

52h 54m

2 stops

1:20 am - 2:55 pm

POS

ORD

14h 35m

1 stop

$575Air Canada

Wed, Sep 16 - Sun, Sep 20

5:35 pm - 8:30 am

ORD

TAB

13h 55m

2 stops

8:45 am - 9:00 am

TAB

ORD

25h 15m

2 stops

$1,601Multiple Airlines

Mon, Aug 24 - Sun, Aug 30

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JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago to Trinidad and Tobago flight tickets

JetBlue

Aug 22

ORD6:00 amChicago O'Hare Intl

11h 20m

1 stop

POS6:20 pmPort of Spain Piarco Intl

Aug 31

POS8:00 pmPort of Spain Piarco Intl

13h 43m

1 stop

ORD8:43 amChicago O'Hare Intl

$456

JetBlue

Aug 22

ORD6:00 amChicago O'Hare Intl

11h 20m

1 stop

POS6:20 pmPort of Spain Piarco Intl

Aug 31

POS8:00 pmPort of Spain Piarco Intl

13h 43m

1 stop

ORD8:43 amChicago O'Hare Intl

$497

JetBlue

Aug 19

ORD6:30 pmChicago O'Hare Intl

18h 14m

1 stop

POS1:44 pmPort of Spain Piarco Intl

Aug 26

POS8:00 pmPort of Spain Piarco Intl

13h 46m

1 stop

ORD8:46 amChicago O'Hare Intl

$540

American Airlines flights from Chicago to Trinidad and Tobago

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

American Airlines

Aug 22

ORD8:19 amChicago O'Hare Intl

13h 59m

2 stops

POS11:18 pmPort of Spain Piarco Intl

Aug 31

POS7:00 amPort of Spain Piarco Intl

14h 30m

2 stops

ORD8:30 pmChicago O'Hare Intl

$634

American Airlines

Aug 19

ORD8:00 amChicago O'Hare Intl

14h 18m

2 stops

POS11:18 pmPort of Spain Piarco Intl

Aug 26

POS7:00 amPort of Spain Piarco Intl

11h 54m

1 stop

ORD5:54 pmChicago O'Hare Intl

$639

American Airlines

Aug 11

ORD6:49 amChicago O'Hare Intl

15h 29m

2 stops

POS11:18 pmPort of Spain Piarco Intl

Aug 17

POS3:15 pmPort of Spain Piarco Intl

17h 19m

1 stop

ORD7:34 amChicago O'Hare Intl

$679

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 - POS

ORDPOS

Chicago O'Hare Intl

Sat 8/22

6:00 am-6:20 pm

1 stop11h 20m

Port of Spain Piarco Intl

Mon 8/31

8:00 pm-8:43 am

1 stop13h 43m

$456

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/28

9:50 am-12:15 am

1 stop13h 25m

Port of Spain Piarco Intl

Fri 10/2

1:20 am-4:58 pm

1 stop16h 38m

$485

Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/28

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Fri 10/2

1:20 am-2:52 pm

2 stops14h 32m

$488

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/28

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Fri 10/2

1:20 am-2:52 pm

2 stops14h 32m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 8/22

6:00 am-6:20 pm

1 stop11h 20m

Port of Spain Piarco Intl

Mon 8/31

8:00 pm-8:43 am

1 stop13h 43m

$497

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/11

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Mon 8/17

1:25 am-1:22 pm

1 stop12h 57m

$533

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/11

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Mon 8/17

1:25 am-2:44 pm

2 stops14h 19m

$536

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 8/19

6:30 pm-1:44 pm

1 stop18h 14m

Port of Spain Piarco Intl

Wed 8/26

8:00 pm-8:46 am

1 stop13h 46m

$540

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/16

6:21 pm-12:15 am

2 stops52h 54m

Port of Spain Piarco Intl

Sun 9/20

1:20 am-2:55 pm

1 stop14h 35m

$575

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Mon 8/24

5:35 pm-8:30 am

2 stops13h 55m

Scarborough ANR Robinson Intl

Sun 8/30

8:45 am-9:00 am

2 stops25h 15m

$1,601

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	11h 20m
Direct flights	None

The fastest flight from Chicago to Trinidad and Tobago takes 11h 20m

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 July 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 1,563 reviews	Search Copa Airlines flights
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,371 reviews	Search Air Canada flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,832 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 10,024 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 $288

Flights to Scarborough, Eastern Tobagofrom $416

Cheap flights from Chicago to Trinidad and Tobago from $219

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 9/17. 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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JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue 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

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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

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

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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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According to popular flight searches on momondo this year