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.

$295 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 55m1 stop Toronto Pearson Intl

9:10 am - 10:00 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 50m2 stops Miami Atlanta Hartsfield-Jackson

$625Multiple Airlines

Thu, Dec 3 - Wed, Dec 9

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

10:10 am - 7:20 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

23h 10m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson

$635Multiple Airlines

Sun, Nov 29 - Sun, Dec 6

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

$648Copa Airlines

Wed, Jan 13 - Wed, Mar 17

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

16h 20m1 stop Panama City Tocumen Intl

2:12 pm - 12:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

24h 34m1 stop Panama City Tocumen Intl

$648Copa Airlines

Wed, Jan 27 - Mon, Feb 1

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

$660American Airlines

Sat, Mar 6 - Sat, Mar 13

9:21 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 57m1 stop Houston George Bush Intcntl

1:25 am - 12:22 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

12h 57m1 stop Houston George Bush Intcntl

$660United Airlines

Thu, Dec 3 - Wed, Dec 9

7:29 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 49m1 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

$660United Airlines

Sun, Nov 29 - Sat, Dec 5

12:40 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 38m1 stop Houston George Bush Intcntl

1:25 am - 2:43 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 18m1 stop Houston George Bush Intcntl

$660United Airlines

Thu, Dec 3 - Tue, Dec 8

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 - 7:10 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 57m1 stop Miami

$664American Airlines

Sat, Mar 6 - Sat, Mar 13

9:01 pm - 2:32 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 31m2 stops Washington, D.C. Reagan-National Miami

3:47 pm - 7:20 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 33m2 stops Miami Washington, D.C. Reagan-National

$664American Airlines

Thu, Apr 15 - Mon, Apr 19

Cheap last minute flights

Enter your travel dates to find the best prices.

7:50 pm - 3:37 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 47m1 stop Miami

4:42 pm - 9:32 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 50m1 stop Miami

$787American Airlines

Tue, Nov 10 - Tue, Nov 17

12:40 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 38m1 stop Houston George Bush Intcntl

1:25 am - 2:51 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 26m1 stop Houston George Bush Intcntl

$787United Airlines

Tue, Nov 10 - Mon, Nov 16

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

9:00 am - 9:23 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

26h 23m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl

$790Multiple Airlines

Thu, Nov 5 - Tue, Nov 10

9:11 pm - 3:37 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 26m2 stops Philadelphia Miami

4:42 pm - 7:26 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 44m2 stops Miami Washington, D.C. Reagan-National

$791American Airlines

Tue, Nov 10 - Tue, Nov 17

9:11 pm - 3:37 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 26m2 stops Philadelphia Miami

4:42 pm - 8:00 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 18m1 stop Miami

$791American Airlines

Tue, Nov 10 - Tue, Nov 17

5:00 am - 3:37 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

8h 37m1 stop Miami

4:42 pm - 8:00 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

17h 18m1 stop Miami

$837American Airlines

Thu, Nov 5 - Tue, Nov 10

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

9:10 am - 5:07 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

33h 57m3 stops Miami Atlanta Hartsfield-Jackson Orlando

$857Multiple Airlines

Thu, Nov 5 - Tue, Nov 10

4:00 pm - 7:30 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

25h 30m1 stop Orlando

12:10 am - 6:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

20h 20m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

$868Multiple Airlines

Sat, Nov 7 - Tue, Nov 17

12:40 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 38m1 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

$917United Airlines

Sat, Nov 7 - Sat, Nov 14

7:29 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 49m1 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

$917United Airlines

Sun, Nov 8 - Sat, Nov 14

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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 3

ORD9:21 amChicago O'Hare Intl

12h 57m

1 stop

POS12:18 amPort of Spain Piarco Intl

Dec 9

POS1:25 amPort of Spain Piarco Intl

12h 57m

1 stop

ORD12:22 pmChicago O'Hare Intl

$660

United Airlines

Dec 11

ORD6:50 amChicago O'Hare Intl

15h 28m

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

$722

United Airlines

Dec 14

ORD7:30 amChicago O'Hare Intl

14h 48m

1 stop

POS12:18 amPort of Spain Piarco Intl

Dec 20

POS2:20 amPort of Spain Piarco Intl

10h 29m

1 stop

ORD10:49 amChicago O'Hare Intl

$761

Air Canada flights from Chicago to Trinidad and Tobago

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

Air Canada

Nov 24

ORD5:58 pmChicago O'Hare Intl

53h 02m

2 stops

POS1:00 amPort of Spain Piarco Intl

Nov 29

POS2:15 amPort of Spain Piarco Intl

31h 45m

2 stops

ORD8:00 amChicago O'Hare Intl

$651

Air Canada

Dec 2

ORD4:30 pmChicago O'Hare Intl

30h 30m

1 stop

POS1:00 amPort of Spain Piarco Intl

Dec 6

POS2:15 amPort of Spain Piarco Intl

15h 23m

1 stop

ORD3:38 pmChicago O'Hare Intl

$676

Air Canada

Dec 5

ORD3:45 pmChicago O'Hare Intl

31h 15m

2 stops

POS1:00 amPort of Spain Piarco Intl

Dec 10

POS2:15 amPort of Spain Piarco Intl

18h 05m

2 stops

ORD6:20 pmChicago O'Hare Intl

$679

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 12/3

10:05 am-1:00 am

1 stop12h 55m

Port of Spain Piarco Intl

Wed 12/9

9:10 am-10:00 pm

2 stops14h 50m

$625

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sun 11/29

8:45 am-1:00 am

1 stop14h 15m

Port of Spain Piarco Intl

Sun 12/6

10:10 am-7:20 am

2 stops23h 10m

$635

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

$648

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Wed 1/27

7:35 am-1:55 am

1 stop16h 20m

Port of Spain Piarco Intl

Mon 2/1

2:12 pm-12:46 pm

1 stop24h 34m

$648

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

$660

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 12/3

9:21 am-12:18 am

1 stop12h 57m

Port of Spain Piarco Intl

Wed 12/9

1:25 am-12:22 pm

1 stop12h 57m

$660

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Sun 11/29

7:29 am-12:18 am

1 stop14h 49m

Port of Spain Piarco Intl

Sat 12/5

1:25 am-10:11 am

1 stop10h 46m

$660

Quickest round-trip

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 12/3

12:40 pm-12:18 am

1 stop9h 38m

Port of Spain Piarco Intl

Tue 12/8

1:25 am-2:43 pm

1 stop15h 18m

$660

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-7:10 am

1 stop16h 57m

$664

ChicagoPort of Spain

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

ORDPOS

Chicago O'Hare Intl

Thu 4/15

9:01 pm-2:32 pm

2 stops16h 31m

Port of Spain Piarco Intl

Mon 4/19

3:47 pm-7:20 am

2 stops16h 33m

$664

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 $629.

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	$295
Fastest flight time	9h 38m
Direct flights	None

The best one-way flight to Trinidad and Tobago from Chicago in the past 72 hours is $295. The best round-trip flight deal from Chicago to Trinidad and Tobago found on momondo in the last 72 hours is $625.

The fastest flight from Chicago to Trinidad and Tobago takes 9h 38m

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 10,460 reviews		Search United Airlines flights
American Airlines	PriceFrom $629	Free Cancellation	Rating 7.0 12,230 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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Popular cities in Trinidad and Tobago

Flights to Port of Spainfrom $280

Flights to Scarborough, Eastern Tobagofrom $470

Cheap flights from Chicago to Trinidad and Tobago from $295

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 12/11. 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?

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

Chicago flight routes

According to popular flight searches on momondo this year

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Fly your favorite airline to Trinidad and Tobago

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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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