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

Air Canada, United Airlines, and American Airlines 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 42% 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 May 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.

$237 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.

8:20 pm - 12:15 am

ORD

POS

26h 55m

1 stop

1:25 am - 1:22 pm

POS

ORD

12h 57m

1 stop

$537Air Canada

Sat, Jun 13 - Fri, Jun 19

8:20 pm - 12:15 am

ORD

POS

26h 55m

1 stop

1:25 am - 6:52 pm

POS

ORD

18h 27m

2 stops

$542Air Canada

Sat, Jun 13 - Fri, Jun 19

9:55 am - 12:15 am

ORD

POS

13h 20m

1 stop

1:25 am - 6:52 pm

POS

ORD

18h 27m

2 stops

$547Air Canada

Fri, Jun 12 - Fri, Jun 19

2:15 pm - 12:15 am

ORD

POS

9h 00m

1 stop

1:25 am - 4:59 pm

POS

ORD

16h 34m

1 stop

$548Air Canada

Fri, May 29 - Sun, May 31

3:40 pm - 12:15 am

ORD

POS

31h 35m

2 stops

1:25 am - 6:52 pm

POS

ORD

18h 27m

2 stops

$551Air Canada

Sat, Jun 13 - Fri, Jun 19

6:00 am - 6:35 pm

ORD

POS

11h 35m

1 stop

7:45 pm - 8:45 am

POS

ORD

14h 00m

1 stop

$605JetBlue

Sat, Jun 13 - Sun, Jun 21

5:22 pm - 1:35 pm

ORD

POS

19h 13m

1 stop

7:45 pm - 8:45 am

POS

ORD

14h 00m

1 stop

$610JetBlue

Fri, Jun 19 - Sun, Jun 21

5:35 pm - 7:40 pm

ORD

POS

25h 05m

2 stops

1:20 am - 2:52 pm

POS

ORD

38h 32m

2 stops

$613Multiple Airlines

Tue, Sep 22 - Fri, Sep 25

6:00 am - 6:35 pm

ORD

POS

11h 35m

1 stop

7:45 pm - 8:45 am

POS

ORD

14h 00m

1 stop

$614JetBlue

Thu, Jun 18 - Sun, Jun 21

8:40 pm - 7:40 pm

ORD

POS

22h 00m

2 stops

1:20 am - 1:23 pm

POS

ORD

13h 03m

1 stop

$616Multiple Airlines

Tue, Sep 22 - Fri, Sep 25

JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago to Trinidad and Tobago flight tickets

JetBlue

Jun 13

ORD6:00 amChicago O'Hare Intl

11h 35m

1 stop

POS6:35 pmPort of Spain Piarco Intl

Jun 21

POS7:45 pmPort of Spain Piarco Intl

14h 00m

1 stop

ORD8:45 amChicago O'Hare Intl

$605

JetBlue

Jun 19

ORD5:22 pmChicago O'Hare Intl

19h 13m

1 stop

POS1:35 pmPort of Spain Piarco Intl

Jun 21

POS7:45 pmPort of Spain Piarco Intl

14h 00m

1 stop

ORD8:45 amChicago O'Hare Intl

$610

JetBlue

Jun 18

ORD6:00 amChicago O'Hare Intl

11h 35m

1 stop

POS6:35 pmPort of Spain Piarco Intl

Jun 21

POS7:45 pmPort of Spain Piarco Intl

14h 00m

1 stop

ORD8:45 amChicago O'Hare Intl

$614

American Airlines flights from Chicago to Trinidad and Tobago

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

American Airlines

Jun 16

ORD8:05 amChicago O'Hare Intl

13h 55m

2 stops

POS11:00 pmPort of Spain Piarco Intl

Jun 25

POS3:13 pmPort of Spain Piarco Intl

10h 06m

1 stop

ORD12:19 amChicago O'Hare Intl

$634

American Airlines

Jul 1

ORD7:10 amChicago O'Hare Intl

14h 50m

2 stops

POS11:00 pmPort of Spain Piarco Intl

Jul 8

POS7:00 amPort of Spain Piarco Intl

16h 01m

1 stop

ORD10:01 pmChicago O'Hare Intl

$651

American Airlines

Jul 13

ORD5:59 pmChicago O'Hare Intl

19h 15m

1 stop

POS2:14 pmPort of Spain Piarco Intl

Aug 2

POS7:00 amPort of Spain Piarco Intl

17h 30m

1 stop

ORD11:30 pmChicago O'Hare Intl

$655

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

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-1:22 pm

1 stop12h 57m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-6:52 pm

2 stops18h 27m

$542

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 6/12

9:55 am-12:15 am

1 stop13h 20m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-6:52 pm

2 stops18h 27m

$547

Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 5/29

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Sun 5/31

1:25 am-4:59 pm

1 stop16h 34m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

3:40 pm-12:15 am

2 stops31h 35m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-6:52 pm

2 stops18h 27m

$551

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Sun 6/21

7:45 pm-8:45 am

1 stop14h 00m

$605

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 6/19

5:22 pm-1:35 pm

1 stop19h 13m

Port of Spain Piarco Intl

Sun 6/21

7:45 pm-8:45 am

1 stop14h 00m

$610

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/22

5:35 pm-7:40 pm

2 stops25h 05m

Port of Spain Piarco Intl

Fri 9/25

1:20 am-2:52 pm

2 stops38h 32m

$613

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 6/18

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Sun 6/21

7:45 pm-8:45 am

1 stop14h 00m

$614

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/22

8:40 pm-7:40 pm

2 stops22h 00m

Port of Spain Piarco Intl

Fri 9/25

1:20 am-1:23 pm

1 stop13h 03m

$616

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, June 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 $317. If you aren’t able to travel to Trinidad and Tobago during the month of June, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $372.

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 25m
Direct flights	None

The fastest flight from Chicago to Trinidad and Tobago takes 9h 25m

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 May 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 $392	Free Cancellation	Rating 7.1 11,062 reviews	Search Air Canada flights
Copa Airlines	PriceFrom $472	Free Cancellation	Rating 7.5 1,577 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $548	Free Cancellation	Rating 7.1 11,650 reviews	Search American Airlines flights
United Airlines	PriceFrom $548	Free Cancellation	Rating 7.4 9,732 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 $302

Flights to Scarborough, Eastern Tobagofrom $417

Cheap flights from Chicago to Trinidad and Tobago from $248

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 6/10. 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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JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue 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

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.

Complete your trip to Trinidad and Tobago

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According to popular flight searches on momondo this year