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 46% 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 is the most popular carrier 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 September 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.

$245 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 - 3:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 20m1 stop Fort Lauderdale

$535Multiple Airlines

Mon, Oct 5 - Mon, Oct 19

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

$537Air Canada

Thu, Oct 15 - Sun, Oct 18

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

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

$541Air Canada

Thu, Oct 15 - Sun, Oct 18

7:28 pm - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

22h 27m2 stops Atlanta Hartsfield-Jackson Miami

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

30h 20m1 stop Fort Lauderdale

$553Multiple Airlines

Mon, Oct 5 - Mon, Oct 19

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

11h 49m1 stop Fort Lauderdale

9:10 am - 11:32 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

27h 22m2 stops Miami Atlanta Hartsfield-Jackson

$557Multiple Airlines

Mon, Oct 5 - Tue, Oct 20

8:45 am - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 30m2 stops Montreal Pierre Elliott Trudeau Intl 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

$579Air Canada

Fri, Oct 16 - Wed, Oct 21

7:10 pm - 1:30 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 20m1 stop Miami

2:30 pm - 12:38 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 08m1 stop Miami

$630American Airlines

Sat, Feb 20 - Thu, Feb 25

6:59 pm - 2:08 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

18h 09m1 stop Miami

3:08 pm - 8:42 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 34m1 stop Miami

$630American Airlines

Sat, Oct 24 - Sat, Oct 31

11:29 am - 1:05 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 36m1 stop Newark

2:20 am - 11:00 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 40m1 stop Newark

$640United Airlines

Fri, Jan 29 - Sat, Feb 6

11:29 am - 1:05 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 36m1 stop Newark

1:30 am - 11:27 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 57m1 stop Houston George Bush Intcntl

$706United Airlines

Sun, Feb 7 - Sun, Feb 21

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American Airlines flights from Chicago to Trinidad and Tobago

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

American Airlines

Oct 24

ORD6:59 pmChicago O'Hare Intl

18h 09m

1 stop

POS2:08 pmPort of Spain Piarco Intl

Oct 31

POS3:08 pmPort of Spain Piarco Intl

18h 34m

1 stop

ORD8:42 amChicago O'Hare Intl

$630

American Airlines

Oct 22

ORD8:55 pmChicago O'Hare Intl

16h 13m

2 stops

POS2:08 pmPort of Spain Piarco Intl

Oct 29

POS3:08 pmPort of Spain Piarco Intl

9h 25m

1 stop

ORD11:33 pmChicago O'Hare Intl

$634

American Airlines

Dec 30

ORD8:35 amChicago O'Hare Intl

13h 10m

1 stop

POS11:45 pmPort of Spain Piarco Intl

Jan 9

POS4:37 pmPort of Spain Piarco Intl

18h 53m

1 stop

ORD9:30 amChicago O'Hare Intl

$635

United Airlines flights from Chicago to Trinidad and Tobago

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

United Airlines

Jan 29

ORD11:29 amChicago O'Hare Intl

11h 36m

1 stop

POS1:05 amPort of Spain Piarco Intl

Feb 6

POS2:20 amPort of Spain Piarco Intl

10h 40m

1 stop

ORD11:00 amChicago O'Hare Intl

$640

United Airlines

Feb 7

ORD11:29 amChicago O'Hare Intl

11h 36m

1 stop

POS1:05 amPort of Spain Piarco Intl

Feb 21

POS1:30 amPort of Spain Piarco Intl

11h 57m

1 stop

ORD11:27 amChicago O'Hare Intl

$706

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 10/5

7:11 am-8:00 pm

1 stop11h 49m

Port of Spain Piarco Intl

Mon 10/19

10:10 am-3:30 pm

1 stop30h 20m

$535

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/15

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 10/18

1:20 am-1:23 pm

1 stop13h 03m

$537

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/15

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 10/18

1:20 am-2:52 pm

2 stops14h 32m

$541

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Mon 10/5

7:28 pm-6:55 pm

2 stops22h 27m

Port of Spain Piarco Intl

Mon 10/19

10:10 am-3:30 pm

1 stop30h 20m

$553

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Mon 10/5

7:11 am-8:00 pm

1 stop11h 49m

Port of Spain Piarco Intl

Tue 10/20

9:10 am-11:32 am

2 stops27h 22m

$557

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 10/16

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Wed 10/21

1:20 am-1:23 pm

1 stop13h 03m

$579

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 2/20

7:10 pm-1:30 pm

1 stop16h 20m

Port of Spain Piarco Intl

Thu 2/25

2:30 pm-12:38 am

1 stop12h 08m

$630

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 10/24

6:59 pm-2:08 pm

1 stop18h 09m

Port of Spain Piarco Intl

Sat 10/31

3:08 pm-8:42 am

1 stop18h 34m

$630

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 1/29

11:29 am-1:05 am

1 stop11h 36m

Port of Spain Piarco Intl

Sat 2/6

2:20 am-11:00 am

1 stop10h 40m

$640

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sun 2/7

11:29 am-1:05 am

1 stop11h 36m

Port of Spain Piarco Intl

Sun 2/21

1:30 am-11:27 am

1 stop11h 57m

$706

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	$245
Fastest flight time	10h 10m
Direct flights	None

The best one-way flight to Trinidad and Tobago from Chicago in the past 72 hours is $245. The best round-trip flight deal from Chicago to Trinidad and Tobago found on momondo in the last 72 hours is $535.

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

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 September 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
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,609 reviews	Search Air Canada flights
United Airlines	PriceFrom $578	Free Cancellation	Rating 7.4 10,194 reviews	Search United Airlines flights
American Airlines	PriceFrom $589	Free Cancellation	Rating 7.1 12,045 reviews	Search American 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 $280

Flights to Scarborough, Eastern Tobagofrom $380

Cheap flights from Chicago to Trinidad and Tobago from $245

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 9/26. 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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American Airlines flights from Chicago to Trinidad and Tobago

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

United Airlines flights from Chicago to Trinidad and Tobago

Our best United 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

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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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