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

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 41% 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 June 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.

$262 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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:55 am - 8:00 pm

ORD

POS

11h 05m

1 stop

10:10 am - 12:25 pm

POS

ORD

27h 15m

1 stop

$538Multiple Airlines

Thu, Aug 20 - Sun, Aug 23

8:05 am - 8:00 pm

ORD

POS

10h 55m

1 stop

10:10 am - 12:15 pm

POS

ORD

27h 05m

1 stop

$549Multiple Airlines

Mon, Jul 13 - Fri, Jul 17

8:05 am - 8:00 pm

ORD

POS

10h 55m

1 stop

10:10 am - 12:15 pm

POS

ORD

27h 05m

1 stop

$563Multiple Airlines

Thu, Jul 9 - Fri, Jul 17

6:00 am - 6:35 pm

ORD

POS

11h 35m

1 stop

7:41 pm - 8:48 am

POS

ORD

14h 07m

1 stop

$585JetBlue

Tue, Aug 4 - Tue, Aug 11

9:50 am - 12:15 am

ORD

POS

13h 25m

1 stop

1:25 am - 1:22 pm

POS

ORD

12h 57m

1 stop

$593Air Canada

Sun, Aug 2 - Fri, Aug 7

8:05 am - 8:00 pm

ORD

POS

10h 55m

1 stop

10:10 am - 12:15 pm

POS

ORD

27h 05m

1 stop

$598Multiple Airlines

Sun, Jul 12 - Fri, Jul 17

7:55 am - 8:00 pm

ORD

POS

11h 05m

1 stop

10:10 am - 8:03 am

POS

ORD

22h 53m

2 stops

$599Multiple Airlines

Thu, Aug 20 - Sun, Aug 23

8:45 am - 12:15 am

ORD

POS

14h 30m

2 stops

1:25 am - 6:47 pm

POS

ORD

18h 22m

2 stops

$602Air Canada

Mon, Jul 13 - Sun, Jul 19

3:45 pm - 12:15 am

ORD

POS

31h 30m

1 stop

1:25 am - 1:22 pm

POS

ORD

12h 57m

1 stop

$603Air Canada

Thu, Jul 2 - Sun, Jul 5

3:45 pm - 12:15 am

ORD

POS

31h 30m

1 stop

1:25 am - 10:16 am

POS

ORD

33h 51m

2 stops

$607Air Canada

Thu, Jul 2 - Sun, Jul 5

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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

Oct 29

ORD12:49 pmChicago O'Hare Intl

9h 34m

1 stop

POS11:23 pmPort of Spain Piarco Intl

Oct 31

POS1:30 amPort of Spain Piarco Intl

10h 37m

1 stop

ORD11:07 amChicago O'Hare Intl

$640

United Airlines

Jul 6

ORD10:25 amChicago O'Hare Intl

11h 58m

1 stop

POS11:23 pmPort of Spain Piarco Intl

Jul 18

POS2:00 amPort of Spain Piarco Intl

10h 04m

1 stop

ORD11:04 amChicago O'Hare Intl

$675

United Airlines

Jun 25

ORD1:30 pmChicago O'Hare Intl

10h 20m

1 stop

POS12:50 amPort of Spain Piarco Intl

Jun 27

POS12:30 amPort of Spain Piarco Intl

11h 00m

1 stop

ORD10:30 amChicago O'Hare Intl

$809

Air Canada flights from Chicago to Trinidad and Tobago

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

Air Canada

Aug 24

ORD8:40 amChicago O'Hare Intl

14h 35m

2 stops

POS12:15 amPort of Spain Piarco Intl

Aug 30

POS1:25 amPort of Spain Piarco Intl

14h 30m

1 stop

ORD2:55 pmChicago O'Hare Intl

$570

Air Canada

Aug 2

ORD9:50 amChicago O'Hare Intl

13h 25m

1 stop

POS12:15 amPort of Spain Piarco Intl

Aug 7

POS1:25 amPort of Spain Piarco Intl

12h 57m

1 stop

ORD1:22 pmChicago O'Hare Intl

$593

Air Canada

Jul 13

ORD8:45 amChicago O'Hare Intl

14h 30m

2 stops

POS12:15 amPort of Spain Piarco Intl

Jul 19

POS1:25 amPort of Spain Piarco Intl

18h 22m

2 stops

ORD6:47 pmChicago O'Hare Intl

$602

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 - POS

ORDPOS

Chicago O'Hare Intl

Thu 8/20

7:55 am-8:00 pm

1 stop11h 05m

Port of Spain Piarco Intl

Sun 8/23

10:10 am-12:25 pm

1 stop27h 15m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/13

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Fri 7/17

10:10 am-12:15 pm

1 stop27h 05m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/9

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Fri 7/17

10:10 am-12:15 pm

1 stop27h 05m

$563

Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/4

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Tue 8/11

7:41 pm-8:48 am

1 stop14h 07m

$585

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 8/2

9:50 am-12:15 am

1 stop13h 25m

Port of Spain Piarco Intl

Fri 8/7

1:25 am-1:22 pm

1 stop12h 57m

$593

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 7/12

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Fri 7/17

10:10 am-12:15 pm

1 stop27h 05m

$598

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 8/20

7:55 am-8:00 pm

1 stop11h 05m

Port of Spain Piarco Intl

Sun 8/23

10:10 am-8:03 am

2 stops22h 53m

$599

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/13

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Sun 7/19

1:25 am-6:47 pm

2 stops18h 22m

$602

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/2

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Sun 7/5

1:25 am-1:22 pm

1 stop12h 57m

$603

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/2

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Sun 7/5

1:25 am-10:16 am

2 stops33h 51m

$607

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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, January 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 $285. If you aren’t able to travel to Trinidad and Tobago during the month of January, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $317.

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	11h 05m
Direct flights	None

The fastest flight from Chicago to Trinidad and Tobago takes 11h 05m

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 June 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 1,567 reviews	Search Copa Airlines flights
Air Canada	PriceFrom $317	Free Cancellation	Rating 7.1 11,218 reviews	Search Air Canada flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,699 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 9,861 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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Popular cities in Trinidad and Tobago

Flights to Port of Spainfrom $280

Flights to Scarborough, Eastern Tobagofrom $454

Cheap flights from Chicago to Trinidad and Tobago from $262

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 7/15. 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

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

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

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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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According to popular flight searches on momondo this year