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 November 2026, there are 2 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.

$307 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.

2:17 pm - 1:27 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

21h 10m1 stop Panama City Tocumen Intl

3:26 am - 12:07 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 41m1 stop Panama City Tocumen Intl

$648Copa Airlines

Sun, Dec 6 - Sat, Jan 16

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

9h 35m1 stop Fort Lauderdale

9:10 am - 11:50 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

28h 40m2 stops Miami Atlanta Hartsfield-Jackson

$663Multiple Airlines

Fri, Jan 22 - Sat, Jan 30

2:13 pm - 1:55 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 42m1 stop Panama City Tocumen Intl

3:26 am - 12:07 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 41m1 stop Panama City Tocumen Intl

$668Copa Airlines

Fri, Jan 15 - Fri, Jan 22

7:35 am - 1:55 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 20m1 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

$668Copa Airlines

Wed, Jan 13 - Wed, Mar 17

5:59 pm - 3:13 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

19h 14m1 stop Miami

4:13 pm - 12:47 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 34m1 stop Miami

$680American Airlines

Sat, Mar 6 - Sat, Mar 13

7:29 pm - 3:13 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 44m1 stop Miami

4:13 pm - 11:59 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

9h 46m1 stop Miami

$680American Airlines

Fri, Mar 5 - Sat, Mar 13

7:30 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 48m1 stop Houston George Bush Intcntl

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

10h 45m1 stop Houston George Bush Intcntl

$680United Airlines

Sat, Dec 5 - Sun, Dec 6

8:27 pm - 3:13 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 46m2 stops Charlotte Douglas Miami

4:13 pm - 6:30 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 17m2 stops Miami Washington, D.C. Reagan-National

$685American Airlines

Sat, Mar 6 - Sat, Mar 13

6:50 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

15h 28m1 stop Houston George Bush Intcntl

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

10h 45m1 stop Houston George Bush Intcntl

$731United Airlines

Fri, Dec 11 - Mon, Jan 11

2:22 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

31h 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

$805United Airlines

Sat, Dec 5 - Sat, Dec 12

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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

Dec 6

ORD2:17 pmChicago O'Hare Intl

21h 10m

1 stop

POS1:27 pmPort of Spain Piarco Intl

Jan 16

POS3:26 amPort of Spain Piarco Intl

22h 41m

1 stop

ORD12:07 amChicago O'Hare Intl

$648

Copa Airlines

Jan 6

ORD7:35 amChicago O'Hare Intl

16h 20m

1 stop

POS1:55 amPort of Spain Piarco Intl

Jan 17

POS3:26 amPort of Spain Piarco Intl

22h 41m

1 stop

ORD12:07 amChicago O'Hare Intl

$668

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

ORD7:30 amChicago O'Hare Intl

14h 48m

1 stop

POS12:18 amPort of Spain Piarco Intl

Dec 6

POS1:25 amPort of Spain Piarco Intl

10h 45m

1 stop

ORD10:10 amChicago O'Hare Intl

$680

United Airlines

Dec 11

ORD6:50 amChicago O'Hare Intl

15h 28m

1 stop

POS12:18 amPort of Spain Piarco Intl

Jan 11

POS1:25 amPort of Spain Piarco Intl

10h 45m

1 stop

ORD10:10 amChicago O'Hare Intl

$731

United Airlines

Dec 5

ORD2:22 pmChicago O'Hare Intl

31h 56m

1 stop

POS12:18 amPort of Spain Piarco Intl

Dec 12

POS1:25 amPort of Spain Piarco Intl

10h 46m

1 stop

ORD10:11 amChicago O'Hare Intl

$805

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

Sun 12/6

2:17 pm-1:27 pm

1 stop21h 10m

Port of Spain Piarco Intl

Sat 1/16

3:26 am-12:07 am

1 stop22h 41m

$648

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 1/22

8:25 am-8:00 pm

1 stop9h 35m

Port of Spain Piarco Intl

Sat 1/30

9:10 am-11:50 am

2 stops28h 40m

$663

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 1/15

2:13 pm-1:55 am

1 stop9h 42m

Port of Spain Piarco Intl

Fri 1/22

3:26 am-12:07 am

1 stop22h 41m

$668

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Wed 1/13

7:35 am-1:55 am

1 stop16h 20m

Port of Spain Piarco Intl

Wed 3/17

2:57 pm-12:44 am

1 stop10h 47m

$668

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 3/6

5:59 pm-3:13 pm

1 stop19h 14m

Port of Spain Piarco Intl

Sat 3/13

4:13 pm-12:47 am

1 stop10h 34m

$680

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 3/5

7:29 pm-3:13 pm

1 stop17h 44m

Port of Spain Piarco Intl

Sat 3/13

4:13 pm-11:59 pm

1 stop9h 46m

$680

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 12/5

7:30 am-12:18 am

1 stop14h 48m

Port of Spain Piarco Intl

Sun 12/6

1:25 am-10:10 am

1 stop10h 45m

$680

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 3/6

8:27 pm-3:13 pm

2 stops16h 46m

Port of Spain Piarco Intl

Sat 3/13

4:13 pm-6:30 am

2 stops16h 17m

$685

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Fri 12/11

6:50 am-12:18 am

1 stop15h 28m

Port of Spain Piarco Intl

Mon 1/11

1:25 am-10:10 am

1 stop10h 45m

$731

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sat 12/5

2:22 pm-12:18 am

1 stop31h 56m

Port of Spain Piarco Intl

Sat 12/12

1:25 am-10:11 am

1 stop10h 46m

$805

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, March 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 $584. If you aren’t able to travel to Trinidad and Tobago during the month of March, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $635.

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	$307
Fastest flight time	9h 35m
Direct flights	None

The best one-way flight to Trinidad and Tobago from Chicago in the past 72 hours is $307. The best round-trip flight deal from Chicago to Trinidad and Tobago found on momondo in the last 72 hours is $648.

The fastest flight from Chicago to Trinidad and Tobago takes 9h 35m

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 November 2026, there are 2 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
United Airlines	PriceFrom $578	Free Cancellation	Rating 7.3 10,475 reviews		Search United Airlines flights
American Airlines	PriceFrom $629	Free Cancellation	Rating 7.0 12,225 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 $280

Flights to Scarborough, Eastern Tobagofrom $471

Cheap flights from Chicago to Trinidad and Tobago from $307

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 11/25. 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

United Airlines flights from Chicago to Trinidad and Tobago

Our best United 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?

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

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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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