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Cheap flights from Chicago to Trinidad and Tobago from $182

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 2/28. 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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0 bags

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Find the cheapest flights from Chicago to Trinidad and Tobago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m2 stops
JetBlue Logo
8:05 am - 9:09 am
POS
-
ORD
26h 04m2 stops
$371JetBlue
jue., mar. 5 - lun., mar. 9
JetBlue Logo
12:41 pm - 7:17 am
ORD
-
POS
16h 36m1 stop
JetBlue Logo
8:05 am - 9:09 am
POS
-
ORD
26h 04m2 stops
$403JetBlue
jue., mar. 5 - lun., mar. 9
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
Air Canada Logo
1:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
$417Air Canada
jue., mar. 5 - dom., mar. 8
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m2 stops
$421Air Canada
sáb., mar. 21 - vie., mar. 27
Air Canada Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
Air Canada Logo
2:20 am - 7:45 pm
POS
-
ORD
19h 25m1 stop
$427Air Canada
mié., ene. 21 - vie., ene. 23
Multiple Airlines Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$440Multiple Airlines
dom., ene. 25 - dom., feb. 1
Multiple Airlines Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$441Multiple Airlines
dom., ene. 25 - dom., feb. 1
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$444JetBlue
dom., ene. 25 - dom., feb. 1
Multiple Airlines Logo
8:00 am - 12:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
3:26 pm - 10:05 am
POS
-
ORD
19h 39m2 stops
$446Multiple Airlines
dom., mar. 22 - lun., mar. 23
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m1 stop
Air Canada Logo
1:20 am - 1:01 pm
POS
-
ORD
12h 41m1 stop
$447Air Canada
jue., mar. 12 - mar., mar. 17

JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago to Trinidad and Tobago flight tickets
JetBlue
Mar 5
ORD10:00 amChicago O'Hare Intl
19h 17m
2 stops
POS7:17 amPort of Spain Piarco Intl
Mar 9
POS8:05 amPort of Spain Piarco Intl
26h 04m
2 stops
ORD9:09 amChicago O'Hare Intl
$371
JetBlue
Mar 5
ORD12:41 pmChicago O'Hare Intl
16h 36m
1 stop
POS7:17 amPort of Spain Piarco Intl
Mar 9
POS8:05 amPort of Spain Piarco Intl
26h 04m
2 stops
ORD9:09 amChicago O'Hare Intl
$403
JetBlue
Jan 25
ORD7:45 amChicago O'Hare Intl
33h 26m
2 stops
POS7:11 pmPort of Spain Piarco Intl
Feb 1
POS8:20 amPort of Spain Piarco Intl
35h 23m
2 stops
ORD5:43 pmChicago O'Hare Intl
$444

Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets
Air Canada
Mar 5
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS1:20 amPort of Spain Piarco Intl
Mar 8
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$417
Air Canada
Mar 21
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS12:20 amPort of Spain Piarco Intl
Mar 27
POS1:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
$421
Air Canada
Jan 21
ORD8:45 pmChicago O'Hare Intl
26h 35m
1 stop
POS1:20 amPort of Spain Piarco Intl
Jan 23
POS2:20 amPort of Spain Piarco Intl
19h 25m
1 stop
ORD7:45 pmChicago O'Hare Intl
$427

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 enero 8, 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

jue. 3/5

10:00 am-7:17 am

2 stops19h 17m

Port of Spain Piarco Intl

lun. 3/9

8:05 am-9:09 am

2 stops26h 04m

$371

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 3/5

12:41 pm-7:17 am

1 stop16h 36m

Port of Spain Piarco Intl

lun. 3/9

8:05 am-9:09 am

2 stops26h 04m

$403

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 3/5

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

dom. 3/8

1:20 am-3:10 pm

1 stop14h 50m

$417

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 3/21

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

vie. 3/27

1:20 am-2:55 pm

2 stops14h 35m

$421

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 1/21

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

vie. 1/23

2:20 am-7:45 pm

1 stop19h 25m

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 1/25

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

dom. 2/1

8:20 am-5:43 pm

2 stops35h 23m

$440

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 1/25

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

dom. 2/1

8:20 am-5:43 pm

2 stops35h 23m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 1/25

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

dom. 2/1

8:20 am-5:43 pm

2 stops35h 23m

$444

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 3/22

8:00 am-12:20 am

1 stop15h 20m

Port of Spain Piarco Intl

lun. 3/23

3:26 pm-10:05 am

2 stops19h 39m

$446

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 3/12

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

mar. 3/17

1:20 am-1:01 pm

1 stop12h 41m

$447

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 52% 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

13h 20m

Direct flights

None
The fastest flight from Chicago to Trinidad and Tobago takes 13h 20m
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
10,603 reviews
Search Air Canada flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,095 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,141 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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Find better results for your trip to Trinidad and Tobago

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