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Trinidad and Tobago

$155+ Cheap flights from Illinois to Trinidad and Tobago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
mar. 21 — mar. 281
sáb. 3/21
sáb. 3/28
1 adult, Economy
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Cheap flight deals from Illinois to Trinidad and Tobago

Cheapest flights from Illinois to Trinidad and Tobago
Explore the most affordable flight options available from Illinois to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 19, 2026.

This Air Canada deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/308:20 pm
ORD
-
POS
1 stop27h 00m
Air Canada
dom. 4/51:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/16$336
This FlightHub deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/289:15 pm
ORD
-
POS
1 stop26h 05m
Air Canada
vie. 4/31:20 am
POS
-
ORD
1 stop11h 43m
Air Canada
Deal found 2/18$352
This Mytrip deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/46:28 pm
ORD
-
POS
1 stop28h 52m
Air Canada
dom. 3/81:20 am
POS
-
ORD
1 stop21h 44m
Air Canada
Deal found 2/18$371
This FlightHub deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/82:15 pm
ORD
-
POS
1 stop9h 00m
Air Canada
lun. 6/151:25 am
POS
-
ORD
1 stop13h 00m
Air Canada
Deal found 2/18$402
This Air Canada deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/247:25 am
ORD
-
POS
2 stops15h 55m
Air Canada
jue. 2/262:20 am
POS
-
ORD
2 stops42h 32m
Air Canada
Deal found 2/19$418
This Air Canada deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/252:15 pm
ORD
-
POS
1 stop9h 00m
Air Canada
dom. 5/311:25 am
POS
-
ORD
1 stop13h 00m
Air Canada
Deal found 2/15$420
This United Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1710:05 am
STL
-
POS
1 stop12h 18m
United Airlines
lun. 3/2312:30 am
POS
-
STL
1 stop9h 51m
United Airlines
Deal found 2/17$590
This Mytrip deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/87:00 am
ORD
-
TAB
2 stops15h 55m
Multiple Airlines
vie. 3/133:00 pm
TAB
-
ORD
2 stops25h 10m
Multiple Airlines
Deal found 2/16$639
This Air Canada deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/234:05 pm
STL
-
POS
1 stop31h 15m
Air Canada
jue. 3/261:20 am
POS
-
STL
1 stop15h 09m
Air Canada
Deal found 2/15$677
This United Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/136:00 am
STL
-
POS
1 stop16h 23m
United Airlines
jue. 3/1912:30 am
POS
-
STL
1 stop9h 51m
United Airlines
Deal found 2/16$782
This United Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/147:00 pm
STL
-
POS
2 stops27h 23m
United Airlines
vie. 3/2012:30 am
POS
-
STL
1 stop9h 51m
United Airlines
Deal found 2/16$789
This United Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/237:00 pm
STL
-
POS
2 stops27h 23m
United Airlines
jue. 3/2612:30 am
POS
-
STL
2 stops18h 30m
United Airlines
Deal found 2/15$824

Find flight deals from Illinois to Trinidad and Tobago

Keep the following information in mind while searching for Illinois to Trinidad and Tobago flight deals. Data was last updated febrero 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$336
(Air Canada)

One-way from

$155
(Air Canada)

Popular in

December

Cheapest in

February

Average price

$475
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
Search Deals
From Illinois to Trinidad and Tobago
Search Deals
One-way flight from Illinois to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 34% potential increase in price ($375 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($90 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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, Cheapflights users made 2,558,603 searches. Data last updated febrero 19, 2026.
Use the filters below to find and compare flights from Illinois to Trinidad and Tobago that are best for you.

Fly from

Illinois

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

dom. 4/5

1:20 am-1:05 pm

1 stop12h 45m

$336

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 3/28

9:15 pm-12:20 am

1 stop26h 05m

Port of Spain Piarco Intl

vie. 4/3

1:20 am-12:03 pm

1 stop11h 43m

$352

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 3/4

6:28 pm-1:20 am

1 stop28h 52m

Port of Spain Piarco Intl

dom. 3/8

1:20 am-10:04 pm

1 stop21h 44m

$371

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

mar. 3/17

10:05 am-11:23 pm

1 stop12h 18m

Port of Spain Piarco Intl

lun. 3/23

12:30 am-9:21 am

1 stop9h 51m

$590

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

dom. 3/8

7:00 am-11:55 pm

2 stops15h 55m

Scarborough ANR Robinson Intl

vie. 3/13

3:00 pm-3:10 pm

2 stops25h 10m

$639

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

lun. 3/23

4:05 pm-12:20 am

1 stop31h 15m

Port of Spain Piarco Intl

jue. 3/26

1:20 am-3:29 pm

1 stop15h 09m

$677

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

vie. 3/13

6:00 am-11:23 pm

1 stop16h 23m

Port of Spain Piarco Intl

jue. 3/19

12:30 am-9:21 am

1 stop9h 51m

$782

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

sáb. 3/14

10:05 am-11:23 pm

1 stop12h 18m

Port of Spain Piarco Intl

vie. 3/20

12:30 am-9:21 am

1 stop9h 51m

$802

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

vie. 7/31

9:50 am-6:10 am

2 stops19h 20m

Scarborough ANR Robinson Intl

mié. 8/5

3:00 pm-2:55 pm

3 stops24h 55m

$961

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 2/24

2:00 pm-1:20 am

1 stop9h 20m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 16 results
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Best time to book a flight from Illinois to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Trinidad and Tobago

What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?

Currently, November is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $435). Flying from Illinois to Trinidad and Tobago in April is currently the most expensive (average of $701). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Trinidad and Tobago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Trinidad and Tobago?

    A quick flight from Illinois to Trinidad and Tobago can take about 12h 18m. Air Canada provides one of the quickest options available for as low as $590. The distance between Illinois and Trinidad and Tobago is about 2641 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Illinois to Trinidad and Tobago that include hotel bookings?

    Yes. In addition to deals on Illinois to Trinidad and Tobago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Trinidad and Tobago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Trinidad and Tobago.

  • Can I find deals for business class flights from Illinois to Trinidad and Tobago?

    Yes. Cheapflights offers flight deals from Illinois to Trinidad and Tobago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?

    Currently, November is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $435). Flying from Illinois to Trinidad and Tobago in April is currently the most expensive (average of $701). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Illinois to Trinidad and Tobago

Discover the top 3 airlines that operate flights from Illinois to Trinidad and Tobago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated febrero 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$501Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$548Average$688FlexibilityNo cancel feeOn-time71%

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