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 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 October 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.

$308 Cheap Flights from Chicago to Trinidad and Tobago in 2026/27

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.

7:35 am - 1:54 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 19m1 stop Panama City Tocumen Intl

3:23 am - 12:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 48m1 stop Panama City Tocumen Intl

$638Copa Airlines

Tue, Nov 24 - Thu, Dec 3

3:13 pm - 2:20 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 07m1 stop Panama City Tocumen Intl

2:57 pm - 12:44 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 47m1 stop Panama City Tocumen Intl

$648Copa Airlines

Sat, Apr 10 - Wed, Apr 14

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 - 1:13 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 58m1 stop Toronto Pearson Intl

$663Air Canada

Fri, Dec 11 - Sun, Jan 10

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

2:15 am - 1:13 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 58m1 stop Toronto Pearson Intl

$664Air Canada

Thu, Dec 10 - Sun, Jan 10

5:00 am - 3:10 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

8h 10m1 stop Miami

3:04 pm - 8:16 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 12m1 stop Miami

$665American Airlines

Wed, Mar 3 - Wed, Mar 17

8:44 pm - 2:32 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 48m2 stops Charlotte Douglas Miami

3:47 pm - 8:47 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 00m2 stops Miami Dallas/Fort Worth

$665American Airlines

Sat, Apr 10 - Wed, Apr 14

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

14h 37m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$666Air Canada

Fri, Dec 11 - Sun, Jan 10

12:40 pm - 12:20 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 40m1 stop Houston George Bush Intcntl

2:20 am - 11:50 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 30m1 stop Newark

$670United Airlines

Sat, Jan 30 - Tue, Feb 2

12:40 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 38m1 stop Houston George Bush Intcntl

1:25 am - 11:15 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 50m1 stop Houston George Bush Intcntl

$670United Airlines

Fri, Nov 27 - Thu, Dec 3

8:25 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 35m1 stop Fort Lauderdale

10:10 am - 10:19 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 09m1 stop Fort Lauderdale

$733Multiple Airlines

Thu, Mar 4 - Mon, Mar 15

Cheap last minute flights

Enter your travel dates to find the best prices.

2:15 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 00m1 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

$627Air Canada

Fri, Oct 16 - Mon, Oct 19

2:15 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 00m1 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

$627Air Canada

Fri, Oct 16 - Mon, Oct 19

2:15 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 00m1 stop Toronto Pearson Intl

1:20 am - 6:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 26m2 stops Toronto Pearson Intl Ottawa

$632Air Canada

Fri, Oct 16 - Mon, Oct 19

2:15 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 00m1 stop Toronto Pearson Intl

1:20 am - 6:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 26m2 stops Toronto Pearson Intl Ottawa

$632Air Canada

Fri, Oct 16 - Mon, Oct 19

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

18h 26m2 stops Toronto Pearson Intl Ottawa

$965Air Canada

Fri, Oct 16 - Mon, Oct 19

7:11 am - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 04m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

1:20 am - 6:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 26m2 stops Toronto Pearson Intl Ottawa

$970Air Canada

Fri, Oct 16 - Mon, Oct 19

8:40 pm - 1:25 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 45m2 stops Toronto Pearson Intl Georgetown Cheddi Jagan Intl

8:30 am - 11:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 00m3 stops Roseau Douglas–Charles San Juan Luis Munoz Marin Intl Fort Lauderdale

$3,032Multiple Airlines

Fri, Oct 16 - Tue, Oct 20

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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

Nov 24

ORD7:35 amChicago O'Hare Intl

16h 19m

1 stop

POS1:54 amPort of Spain Piarco Intl

Dec 3

POS3:23 amPort of Spain Piarco Intl

22h 48m

1 stop

ORD12:11 amChicago O'Hare Intl

$638

Copa Airlines

Apr 10

ORD3:13 pmChicago O'Hare Intl

10h 07m

1 stop

POS2:20 amPort of Spain Piarco Intl

Apr 14

POS2:57 pmPort of Spain Piarco Intl

10h 47m

1 stop

ORD12:44 amChicago O'Hare Intl

$648

Copa Airlines

Nov 8

ORD7:35 amChicago O'Hare Intl

27h 42m

1 stop

POS1:17 pmPort of Spain Piarco Intl

Nov 14

POS3:40 amPort of Spain Piarco Intl

11h 06m

1 stop

ORD12:46 pmChicago O'Hare Intl

$761

Air Canada flights from Chicago to Trinidad and Tobago

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

Air Canada

Oct 16

ORD2:15 pmChicago O'Hare Intl

9h 00m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 19

POS1:20 amPort of Spain Piarco Intl

14h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$627

Air Canada

Oct 16

ORD2:15 pmChicago O'Hare Intl

9h 00m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 19

POS1:20 amPort of Spain Piarco Intl

18h 26m

2 stops

ORD6:46 pmChicago O'Hare Intl

$632

Air Canada

Dec 11

ORD10:05 amChicago O'Hare Intl

12h 55m

1 stop

POS1:00 amPort of Spain Piarco Intl

Jan 10

POS2:15 amPort of Spain Piarco Intl

12h 58m

1 stop

ORD1:13 pmChicago O'Hare Intl

$663

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 11/24

7:35 am-1:54 am

1 stop16h 19m

Port of Spain Piarco Intl

Thu 12/3

3:23 am-12:11 am

1 stop22h 48m

$638

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 4/10

3:13 pm-2:20 am

1 stop10h 07m

Port of Spain Piarco Intl

Wed 4/14

2:57 pm-12:44 am

1 stop10h 47m

$648

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 12/11

10:05 am-1:00 am

1 stop12h 55m

Port of Spain Piarco Intl

Sun 1/10

2:15 am-1:13 pm

1 stop12h 58m

$663

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 12/10

8:45 am-1:00 am

1 stop14h 15m

Port of Spain Piarco Intl

Sun 1/10

2:15 am-1:13 pm

1 stop12h 58m

$664

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Wed 3/3

5:00 am-3:10 pm

1 stop8h 10m

Port of Spain Piarco Intl

Wed 3/17

3:04 pm-8:16 am

1 stop18h 12m

$665

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 4/10

8:44 pm-2:32 pm

2 stops16h 48m

Port of Spain Piarco Intl

Wed 4/14

3:47 pm-8:47 am

2 stops18h 00m

$665

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 12/11

10:05 am-1:00 am

1 stop12h 55m

Port of Spain Piarco Intl

Sun 1/10

2:15 am-2:52 pm

2 stops14h 37m

$666

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 1/30

12:40 pm-12:20 am

1 stop9h 40m

Port of Spain Piarco Intl

Tue 2/2

2:20 am-11:50 am

1 stop11h 30m

$670

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 11/27

12:40 pm-12:18 am

1 stop9h 38m

Port of Spain Piarco Intl

Thu 12/3

1:25 am-11:15 am

1 stop11h 50m

$670

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 3/4

8:25 am-8:00 pm

1 stop9h 35m

Port of Spain Piarco Intl

Mon 3/15

10:10 am-10:19 pm

1 stop13h 09m

$733

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 July is also cheap. Prices for this month can be found on momondo for an average of $629.

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	$308
Fastest flight time	10h 07m
Direct flights	None

The best one-way flight to Trinidad and Tobago from Chicago in the past 72 hours is $308. The best round-trip flight deal from Chicago to Trinidad and Tobago found on momondo in the last 72 hours is $638.

The fastest flight from Chicago to Trinidad and Tobago takes 10h 07m

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 October 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 11,774 reviews	Search Air Canada flights
United Airlines	PriceFrom $578	Free Cancellation	Rating 7.4 10,362 reviews	Search United Airlines flights
American Airlines	PriceFrom $623	Free Cancellation	Rating 7.0 12,170 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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Popular cities in Trinidad and Tobago

Flights to Port of Spainfrom $280

Flights to Scarborough, Eastern Tobagofrom $494

Cheap flights from Chicago to Trinidad and Tobago from $308

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 12/2. 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

Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada 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

According to popular flight searches on momondo this year

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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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