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 March 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.

$170 Cheap Flights from Chicago to Trinidad and Tobago in 2026

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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.

9:50 am - 12:20 am

ORD

POS

13h 30m

1 stop

1:20 am - 5:50 pm

POS

ORD

17h 30m

1 stop

$388Air Canada

Per, Nis 9 - Paz, Nis 12

9:20 pm - 12:20 am

ORD

POS

26h 00m

1 stop

1:20 am - 1:05 pm

POS

ORD

12h 45m

1 stop

$393Air Canada

Çar, Nis 8 - Paz, Nis 12

1:55 pm - 12:20 am

ORD

POS

33h 25m

2 stops

1:20 am - 7:58 am

POS

ORD

31h 38m

2 stops

$398Air Canada

Çar, Nis 8 - Paz, Nis 12

1:55 pm - 12:20 am

ORD

POS

33h 25m

2 stops

1:20 am - 8:00 am

POS

ORD

31h 40m

2 stops

$401Air Canada

Pzt, Mar 30 - Paz, Nis 5

9:20 pm - 12:20 am

ORD

POS

26h 00m

1 stop

1:20 am - 1:05 pm

POS

ORD

12h 45m

1 stop

$418Air Canada

Çar, Nis 8 - Cum, Nis 10

10:37 am - 12:20 am

ORD

POS

36h 43m

2 stops

1:20 am - 7:25 pm

POS

ORD

19h 05m

1 stop

$423Air Canada

Per, Nis 2 - Per, Nis 9

9:05 am - 12:20 am

ORD

POS

14h 15m

1 stop

5:38 pm - 9:36 pm

POS

ORD

28h 58m

2 stops

$468Multiple Airlines

Paz, Nis 26 - Paz, May 3

7:13 am - 12:20 am

ORD

POS

16h 07m

2 stops

5:38 pm - 9:36 pm

POS

ORD

28h 58m

2 stops

$471Multiple Airlines

Paz, Nis 26 - Paz, May 3

6:40 pm - 12:20 am

ORD

POS

28h 40m

1 stop

1:20 am - 8:03 am

POS

ORD

31h 43m

1 stop

$473Air Canada

Per, Nis 2 - Per, Nis 9

6:40 pm - 12:20 am

ORD

POS

28h 40m

1 stop

1:20 am - 2:55 pm

POS

ORD

14h 35m

2 stops

$476Air Canada

Per, Nis 2 - Per, Nis 9

Air Canada flights from Chicago to Trinidad and Tobago

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

Air Canada

Apr 9

ORD9:50 amChicago O'Hare Intl

13h 30m

1 stop

POS12:20 amPort of Spain Piarco Intl

Apr 12

POS1:20 amPort of Spain Piarco Intl

17h 30m

1 stop

ORD5:50 pmChicago O'Hare Intl

$388

Air Canada

Apr 8

ORD9:20 pmChicago O'Hare Intl

26h 00m

1 stop

POS12:20 amPort of Spain Piarco Intl

Apr 12

POS1:20 amPort of Spain Piarco Intl

12h 45m

1 stop

ORD1:05 pmChicago O'Hare Intl

$393

Air Canada

Apr 8

ORD1:55 pmChicago O'Hare Intl

33h 25m

2 stops

POS12:20 amPort of Spain Piarco Intl

Apr 12

POS1:20 amPort of Spain Piarco Intl

31h 38m

2 stops

ORD7:58 amChicago O'Hare Intl

$398

Copa Airlines flights from Chicago to Trinidad and Tobago

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

Copa Airlines

May 9

ORD8:02 amChicago O'Hare Intl

16h 44m

1 stop

POS1:46 amPort of Spain Piarco Intl

May 20

POS2:22 pmPort of Spain Piarco Intl

11h 53m

1 stop

ORD1:15 amChicago O'Hare Intl

$565

Copa Airlines

Mar 16

ORD8:34 amChicago O'Hare Intl

16h 12m

1 stop

POS1:46 amPort of Spain Piarco Intl

Mar 18

POS2:16 pmPort of Spain Piarco Intl

11h 48m

1 stop

ORD1:04 amChicago O'Hare Intl

$579

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

Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Per 4/9

9:50 am-12:20 am

1 stop13h 30m

Port of Spain Piarco Intl

Paz 4/12

1:20 am-5:50 pm

1 stop17h 30m

$388

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Çar 4/8

9:20 pm-12:20 am

1 stop26h 00m

Port of Spain Piarco Intl

Paz 4/12

1:20 am-1:05 pm

1 stop12h 45m

$393

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Çar 4/8

1:55 pm-12:20 am

2 stops33h 25m

Port of Spain Piarco Intl

Paz 4/12

1:20 am-7:58 am

2 stops31h 38m

$398

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Pzt 3/30

1:55 pm-12:20 am

2 stops33h 25m

Port of Spain Piarco Intl

Paz 4/5

1:20 am-8:00 am

2 stops31h 40m

$401

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Çar 4/8

9:20 pm-12:20 am

1 stop26h 00m

Port of Spain Piarco Intl

Cum 4/10

1:20 am-1:05 pm

1 stop12h 45m

$418

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Per 4/2

10:37 am-12:20 am

2 stops36h 43m

Port of Spain Piarco Intl

Per 4/9

1:20 am-7:25 pm

1 stop19h 05m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Paz 4/26

9:05 am-12:20 am

1 stop14h 15m

Port of Spain Piarco Intl

Paz 5/3

5:38 pm-9:36 pm

2 stops28h 58m

$468

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Paz 4/26

7:13 am-12:20 am

2 stops16h 07m

Port of Spain Piarco Intl

Paz 5/3

5:38 pm-9:36 pm

2 stops28h 58m

$471

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Per 4/2

6:40 pm-12:20 am

1 stop28h 40m

Port of Spain Piarco Intl

Per 4/9

1:20 am-8:03 am

1 stop31h 43m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Per 4/2

6:40 pm-12:20 am

1 stop28h 40m

Port of Spain Piarco Intl

Per 4/9

1:20 am-2:55 pm

2 stops14h 35m

$476

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

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

JetBlue and Air Canada are the most popular carriers 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.

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	9h 00m
Direct flights	None

The fastest flight from Chicago to Trinidad and Tobago takes 9h 00m

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

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 March 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
Air Canada	PriceFrom $397	Free Cancellation	Rating 7.1 10,800 reviews	Search Air Canada flights
Copa Airlines	PriceFrom $472	Free Cancellation	Rating 7.5 1,570 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,464 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 9,423 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.

An easier way to manage your Trinidad and Tobago trip

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Popular cities in Trinidad and Tobago

Flights to Port of Spainfrom $282

Flights to Scarborough, Eastern Tobagofrom $391

Cheap flights from Chicago to Trinidad and Tobago from $170

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 4/9. 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

Copa Airlines flights from Chicago to Trinidad and Tobago

Our best Copa 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 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

Find info about flight duration, direct flights, and airports for your flight from Chicago to Trinidad and Tobago

Fastest flight time

Direct flights

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

Trinidad and Tobago flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Trinidad and Tobago

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Cabin classes currently available on flights to Trinidad and Tobago

List of cabin classes available on flights landing in Trinidad and Tobago. Availability may vary depending on flight origin and airline.

Complete your trip to Trinidad and Tobago

Explore popular destinations other users love

According to popular flight searches on momondo this year