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 45% 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.

$247 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

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

14h 35m1 stop Toronto Pearson Intl

$577Air 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 - 1:23 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 03m1 stop Toronto Pearson Intl

$577Air Canada

Sat, Oct 17 - Fri, Oct 23

3:45 pm - 12:15 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

31h 30m1 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

$580Air Canada

Thu, Oct 22 - Sun, Nov 1

8:04 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 56m1 stop Fort Lauderdale

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

30h 20m1 stop Fort Lauderdale

$594Multiple Airlines

Thu, Oct 22 - Sun, Oct 25

8:04 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 56m1 stop Fort Lauderdale

9:10 am - 9:21 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

25h 11m2 stops Miami Atlanta Hartsfield-Jackson

$608Multiple Airlines

Thu, Oct 22 - Sun, Oct 25

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

16h 46m1 stop Panama City Tocumen Intl

3:40 am - 12:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 31m1 stop Panama City Tocumen Intl

$618Copa Airlines

Fri, Oct 23 - Sat, Oct 31

10:34 am - 11:18 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 44m1 stop Houston George Bush Intcntl

1:25 am - 11:17 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 52m1 stop Houston George Bush Intcntl

$630United Airlines

Thu, Oct 29 - Wed, Nov 11

10:34 am - 12:30 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 56m1 stop Houston George Bush Intcntl

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

10h 46m1 stop Houston George Bush Intcntl

$630United Airlines

Sat, Oct 31 - Fri, Nov 6

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

18h 09m1 stop Miami

3:08 pm - 12:38 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 30m1 stop Miami

$630American Airlines

Sat, Oct 17 - Sat, Oct 31

6:00 am - 11:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

15h 35m1 stop Miami

4:42 pm - 9:30 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 48m1 stop Miami

$630American Airlines

Fri, Dec 4 - Sat, Dec 12

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United Airlines flights from Chicago to Trinidad and Tobago

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

United Airlines

Dec 5

ORD10:30 amChicago O'Hare Intl

11h 48m

1 stop

POS12:18 amPort of Spain Piarco Intl

Dec 12

POS1:25 amPort of Spain Piarco Intl

13h 02m

1 stop

ORD12:27 pmChicago O'Hare Intl

$750

United Airlines

Sep 4

ORD12:16 pmChicago O'Hare Intl

11h 34m

1 stop

POS12:50 amPort of Spain Piarco Intl

Sep 7

POS2:00 amPort of Spain Piarco Intl

11h 08m

1 stop

ORD12:08 pmChicago O'Hare Intl

$849

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 15

ORD8:40 pmChicago O'Hare Intl

26h 35m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 18

POS1:20 amPort of Spain Piarco Intl

14h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$577

Air Canada

Oct 22

ORD3:45 pmChicago O'Hare Intl

31h 30m

1 stop

POS12:15 amPort of Spain Piarco Intl

Nov 1

POS2:15 amPort of Spain Piarco Intl

15h 23m

1 stop

ORD3:38 pmChicago O'Hare Intl

$580

Air Canada

Oct 15

ORD8:40 pmChicago O'Hare Intl

26h 35m

1 stop

POS12:15 amPort of Spain Piarco Intl

Oct 18

POS1:20 amPort of Spain Piarco Intl

14h 32m

2 stops

ORD2:52 pmChicago O'Hare Intl

$581

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 10/15

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 10/18

1:20 am-2:55 pm

1 stop14h 35m

$577

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 10/17

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 10/23

1:20 am-1:23 pm

1 stop13h 03m

$577

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/22

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Sun 11/1

2:15 am-3:38 pm

1 stop15h 23m

$580

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/22

8:04 am-8:00 pm

1 stop10h 56m

Port of Spain Piarco Intl

Sun 10/25

10:10 am-3:30 pm

1 stop30h 20m

$594

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/22

8:04 am-8:00 pm

1 stop10h 56m

Port of Spain Piarco Intl

Sun 10/25

9:10 am-9:21 am

2 stops25h 11m

$608

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 10/23

8:01 am-1:47 am

1 stop16h 46m

Port of Spain Piarco Intl

Sat 10/31

3:40 am-12:11 am

1 stop22h 31m

$618

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 10/29

10:34 am-11:18 pm

1 stop11h 44m

Port of Spain Piarco Intl

Wed 11/11

1:25 am-11:17 am

1 stop11h 52m

$630

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 10/31

10:34 am-12:30 am

1 stop12h 56m

Port of Spain Piarco Intl

Fri 11/6

1:25 am-10:11 am

1 stop10h 46m

$630

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 10/17

6:59 pm-2:08 pm

1 stop18h 09m

Port of Spain Piarco Intl

Sat 10/31

3:08 pm-12:38 am

1 stop10h 30m

$630

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 12/4

6:00 am-11:35 pm

1 stop15h 35m

Port of Spain Piarco Intl

Sat 12/12

4:42 pm-9:30 am

1 stop18h 48m

$630

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	$247
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 $247. The best round-trip flight deal from Chicago to Trinidad and Tobago found on momondo in the last 72 hours is $577.

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 11,573 reviews	Search Air Canada flights
United Airlines	PriceFrom $578	Free Cancellation	Rating 7.4 10,159 reviews	Search United Airlines flights
American Airlines	PriceFrom $589	Free Cancellation	Rating 7.1 12,029 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 $270

Flights to Scarborough, Eastern Tobagofrom $361

Cheap flights from Chicago to Trinidad and Tobago from $247

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 10/13. 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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United Airlines flights from Chicago to Trinidad and Tobago

Our best United 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

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