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

JetBlue is the most popular carrier operating from Chicago to Trinidad and Tobago

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.

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.

$209 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

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6:00 am - 6:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 35m1 stop New York John F Kennedy Intl

8:00 pm - 8:43 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 43m1 stop New York John F Kennedy Intl

$472JetBlue

Tue, Aug 25 - Tue, Sep 1

6:00 am - 6:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 35m1 stop New York John F Kennedy Intl

8:00 pm - 8:42 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 42m1 stop New York John F Kennedy Intl

$472JetBlue

Tue, Sep 1 - Sat, Sep 5

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

14h 35m1 stop Toronto Pearson Intl

$530Air Canada

Sat, Sep 19 - Fri, Sep 25

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

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

$534Air Canada

Sat, Sep 19 - Fri, Sep 25

3:20 pm - 1:47 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 27m1 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

Mon, Sep 14 - Tue, Sep 29

8:01 am - 1:17 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

28h 16m1 stop Panama City Tocumen Intl

3:50 am - 12:57 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 07m1 stop Panama City Tocumen Intl

$568Copa Airlines

Tue, Sep 29 - Mon, Oct 12

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 - 7:42 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 36m2 stops Miami Dallas/Fort Worth

$572American Airlines

Sat, Sep 19 - Sat, Sep 26

8:00 am - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 18m2 stops Washington, D.C. Reagan-National Miami

7:00 am - 8:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 30m2 stops Miami Dallas/Fort Worth

$584American Airlines

Tue, Aug 25 - Tue, Sep 1

1:30 pm - 12:50 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 20m1 stop Newark

12:30 am - 4:41 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 11m1 stop Houston George Bush Intcntl

$821United Airlines

Thu, Aug 20 - Tue, Sep 29

10:25 am - 12:50 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

13h 25m1 stop Newark

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

10h 59m1 stop Newark

$990United Airlines

Mon, Aug 17 - Tue, Aug 18

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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 19

ORD3:45 pmChicago O'Hare Intl

31h 30m

1 stop

POS12:15 amPort of Spain Piarco Intl

Sep 25

POS1:20 amPort of Spain Piarco Intl

14h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$530

Air Canada

Sep 19

ORD8:40 pmChicago O'Hare Intl

26h 35m

1 stop

POS12:15 amPort of Spain Piarco Intl

Sep 25

POS1:20 amPort of Spain Piarco Intl

19h 52m

2 stops

ORD8:12 pmChicago O'Hare Intl

$534

Air Canada

Sep 24

ORD8:40 pmChicago O'Hare Intl

26h 35m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 2

POS1:20 amPort of Spain Piarco Intl

14h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$555

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 19

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

17h 36m

2 stops

ORD7:42 amChicago O'Hare Intl

$572

American Airlines

Aug 25

ORD8:00 amChicago O'Hare Intl

14h 18m

2 stops

POS11:18 pmPort of Spain Piarco Intl

Sep 1

POS7:00 amPort of Spain Piarco Intl

14h 30m

2 stops

ORD8:30 pmChicago O'Hare Intl

$584

American Airlines

Aug 25

ORD6:00 amChicago O'Hare Intl

16h 18m

1 stop

POS11:18 pmPort of Spain Piarco Intl

Aug 30

POS3:15 pmPort of Spain Piarco Intl

9h 15m

1 stop

ORD11:30 pmChicago O'Hare Intl

$585

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

Tue 8/25

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Tue 9/1

8:00 pm-8:43 am

1 stop13h 43m

$472

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 9/1

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Sat 9/5

8:00 pm-8:42 am

1 stop13h 42m

$472

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 9/19

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Fri 9/25

1:20 am-2:55 pm

1 stop14h 35m

$530

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 9/19

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 9/25

1:20 am-8:12 pm

2 stops19h 52m

$534

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Mon 9/14

3:20 pm-1:47 am

1 stop9h 27m

Port of Spain Piarco Intl

Tue 9/29

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 9/29

8:01 am-1:17 pm

1 stop28h 16m

Port of Spain Piarco Intl

Mon 10/12

3:50 am-12:57 am

1 stop22h 07m

$568

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 9/19

8:55 pm-2:06 pm

2 stops16h 11m

Port of Spain Piarco Intl

Sat 9/26

3:06 pm-7:42 am

2 stops17h 36m

$572

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Tue 8/25

8:00 am-11:18 pm

2 stops14h 18m

Port of Spain Piarco Intl

Tue 9/1

7:00 am-8:30 pm

2 stops14h 30m

$584

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 8/20

1:30 pm-12:50 am

1 stop10h 20m

Port of Spain Piarco Intl

Tue 9/29

12:30 am-4:41 pm

1 stop17h 11m

$821

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Mon 8/17

10:25 am-12:50 am

1 stop13h 25m

Port of Spain Piarco Intl

Tue 8/18

2:00 am-11:59 am

1 stop10h 59m

$990

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	12h 55m
Direct flights	None

The fastest flight from Chicago to Trinidad and Tobago takes 12h 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 1,563 reviews	Search Copa Airlines flights
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,434 reviews	Search Air Canada flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,875 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 10,080 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 $379

Cheap flights from Chicago to Trinidad and Tobago from $209

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 8/28. 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

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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

Popular cities in 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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