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Cheap flights from Chicago to Trinidad and Tobago from $205

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 2/15. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
2:20 am - 3:10 pm
POS
-
ORD
14h 50m
1 stop
$358Air Canada
ven., févr. 27 - jeu., mars 5
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
2:20 am - 6:52 pm
POS
-
ORD
42h 32m
2 stops
$368Air Canada
ven., févr. 27 - jeu., mars 5
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
13h 45m
1 stop
Multiple Airlines Logo
10:10 am - 7:46 pm
POS
-
ORD
10h 36m
1 stop
$437Multiple Airlines
dim., mars 8 - lun., mars 16
Multiple Airlines Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m
2 stops
Multiple Airlines Logo
1:20 am - 7:45 pm
POS
-
ORD
19h 25m
1 stop
$446Multiple Airlines
mer., mars 4 - jeu., mars 12
Multiple Airlines Logo
8:00 am - 12:20 am
ORD
-
POS
15h 20m
1 stop
Multiple Airlines Logo
3:26 pm - 10:10 am
POS
-
ORD
19h 44m
2 stops
$451Multiple Airlines
dim., mars 8 - lun., mars 16
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 3:10 pm
POS
-
ORD
14h 50m
1 stop
$458Air Canada
mer., mars 4 - mar., mars 10
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 1:25 pm
POS
-
ORD
13h 00m
1 stop
$461Air Canada
mer., mai 6 - dim., mai 10
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$463Air Canada
mer., mars 4 - mar., mars 10
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 6:53 pm
POS
-
ORD
18h 28m
2 stops
$466Air Canada
mer., mai 6 - dim., mai 10
Air Canada Logo
6:04 pm - 1:20 am
ORD
-
POS
29h 16m
2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
42h 32m
2 stops
$468Air Canada
mer., mars 4 - mar., mars 10

JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago to Trinidad and Tobago flight tickets
JetBlue
Mar 8
ORD10:00 amChicago O'Hare Intl
19h 17m
2 stops
POS6:17 amPort of Spain Piarco Intl
Mar 16
POS3:26 pmPort of Spain Piarco Intl
19h 44m
2 stops
ORD10:10 amChicago O'Hare Intl
$547
JetBlue
Jun 5
ORD3:15 pmChicago O'Hare Intl
22h 06m
1 stop
POS2:21 pmPort of Spain Piarco Intl
Jun 8
POS3:50 pmPort of Spain Piarco Intl
18h 58m
1 stop
ORD9:48 amChicago O'Hare Intl
$583
JetBlue
Feb 11
ORD6:00 pmChicago O'Hare Intl
38h 57m
2 stops
POS10:57 amPort of Spain Piarco Intl
Feb 26
POS9:05 amPort of Spain Piarco Intl
26h 05m
2 stops
ORD9:10 amChicago O'Hare Intl
$717

Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets
Air Canada
Feb 27
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS1:20 amPort of Spain Piarco Intl
Mar 5
POS2:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$358
Air Canada
Feb 27
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS1:20 amPort of Spain Piarco Intl
Mar 5
POS2:20 amPort of Spain Piarco Intl
42h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$368
Air Canada
Mar 4
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS1:20 amPort of Spain Piarco Intl
Mar 12
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$458

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Trinidad and Tobago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated janvier 29, 2026.
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

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven. 2/27

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

jeu. 3/5

2:20 am-3:10 pm

1 stop14h 50m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven. 2/27

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

jeu. 3/5

2:20 am-6:52 pm

2 stops42h 32m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dim. 3/8

5:15 am-8:00 pm

1 stop13h 45m

Port of Spain Piarco Intl

lun. 3/16

10:10 am-7:46 pm

1 stop10h 36m

$437

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 3/4

10:00 am-7:17 am

2 stops19h 17m

Port of Spain Piarco Intl

jeu. 3/12

1:20 am-7:45 pm

1 stop19h 25m

$446

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dim. 3/8

8:00 am-12:20 am

1 stop15h 20m

Port of Spain Piarco Intl

lun. 3/16

3:26 pm-10:10 am

2 stops19h 44m

$451

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 3/4

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

mar. 3/10

1:20 am-3:10 pm

1 stop14h 50m

$458

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 5/6

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

dim. 5/10

1:25 am-1:25 pm

1 stop13h 00m

$461

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 3/4

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

mar. 3/10

1:20 am-6:52 pm

2 stops18h 32m

$463

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 5/6

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

dim. 5/10

1:25 am-6:53 pm

2 stops18h 28m

$466

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 3/4

6:04 pm-1:20 am

2 stops29h 16m

Port of Spain Piarco Intl

mar. 3/10

1:20 am-6:52 pm

2 stops42h 32m

$468

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Trinidad and Tobago from

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?

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 51% of people opting to fly with this airline when traveling to Trinidad and Tobago. Keep in mind that there are 3 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

12h 45m

Direct flights

None
The fastest flight from Chicago to Trinidad and Tobago takes 12h 45m
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?

  • 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 CanadaPriceFrom $432Free CancellationRating
7.1
10,667 reviews
Search Air Canada flights
United AirlinesPriceFrom $501Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,206 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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Find better results for your trip to Trinidad and Tobago

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