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Trinidad and Tobago

$188+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap 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 septiembre 16, 2025.

Round-trip from

$423
(Air Canada)

One-way from

$188
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$618
From Illinois to Trinidad and Tobago
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One-way flight from Illinois to Trinidad and Tobago
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Highest demand for flights based on searches. 6% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($66 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 septiembre 16, 2025.

This Air Canada deal was found by Cheapflights users on 9/14. 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. 9/152:00 pmORD - POS
1 stop10h 20mAir Canada
vie. 9/262:25 amPOS - ORD
1 stop11h 49mAir Canada
Deal found 9/14$423
This Air Canada deal was found by Cheapflights users on 9/13. 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.
vie. 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
vie. 11/282:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 9/13$428
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/224:05 pmSTL - POS
1 stop31h 05mAir Canada
vie. 11/282:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 9/16$433
This Air Canada deal was found by Cheapflights users on 9/13. 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.
vie. 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
jue. 11/272:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 9/13$473
This Air Canada deal was found by Cheapflights users on 9/16. 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.
sáb. 11/224:05 pmSTL - POS
1 stop31h 05mAir Canada
mar. 11/252:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 9/16$483
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/227:43 pmORD - POS
2 stops29h 03mMultiple Airlines
dom. 10/266:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Deal found 9/15$492
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/41:35 pmORD - POS
2 stops21h 42mMultiple Airlines
jue. 12/119:10 amPOS - ORD
1 stop29h 20mMultiple Airlines
Deal found 9/15$519
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/63:07 pmORD - POS
1 stop9h 39mCopa Airlines
mié. 10/82:40 pmPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 9/14$532
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/204:05 pmSTL - POS
1 stop31h 05mAir Canada
jue. 11/272:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 9/16$533
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/147:43 pmORD - POS
2 stops29h 03mMultiple Airlines
mar. 10/218:55 amPOS - ORD
1 stop28h 50mMultiple Airlines
Deal found 9/16$536
This United Airlines deal was found by Cheapflights users on 9/14. 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.
jue. 9/187:00 amORD - POS
1 stop15h 23mUnited Airlines
mié. 10/1512:30 amPOS - ORD
1 stop10h 40mUnited Airlines
Deal found 9/14$548
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:57 amSTL - POS
1 stop8h 03mMultiple Airlines
jue. 11/610:10 amPOS - STL
2 stops31h 51mMultiple Airlines
Deal found 9/15$558

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 septiembre 16, 2025.
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

vie. 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

vie. 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 2/2

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

dom. 2/8

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

vie. 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 3/6

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

jue. 3/12

1:15 am-8:05 am

2 stops31h 50m

$433

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

sáb. 11/22

4:05 pm-1:10 am

1 stop31h 05m

Port of Spain Piarco Intl

mar. 11/25

2:15 am-3:29 pm

1 stop15h 14m

$483

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

jue. 11/20

4:05 pm-1:10 am

1 stop31h 05m

Port of Spain Piarco Intl

vie. 11/28

2:15 am-3:29 pm

1 stop15h 14m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 10/22

7:43 pm-1:46 am

2 stops29h 03m

Port of Spain Piarco Intl

dom. 10/26

6:25 pm-9:22 am

1 stop15h 57m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 11/21

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

jue. 11/27

2:15 am-1:01 pm

1 stop12h 46m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 10/6

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

mié. 10/8

2:40 pm-12:21 am

1 stop10h 41m

$532

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 1/5

10:35 am-12:23 am

1 stop11h 48m

Port of Spain Piarco Intl

lun. 1/12

1:30 am-7:50 pm

1 stop20h 20m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 31 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, October 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 December is currently the most expensive (average of $710). 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.

What is the cheapest time of day to fly from IL to TT?

Find hourly flight availability from Illinois to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Trinidad and Tobago as you normally would.

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 9h 10m. Air Canada provides one of the quickest options available for as low as $423. The distance between Illinois and Trinidad and Tobago is about 2697 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, October 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 December is currently the most expensive (average of $710). 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$622FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$566FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$516Average$556FlexibilityNo cancel feeOn-time67%

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