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Trinidad

$188+ Cheap flights from Illinois to Trinidad

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Illinois to Trinidad

Keep the following information in mind while searching for Illinois to Trinidad flight deals. Data was last updated September 17, 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
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One-way flight from Illinois to Trinidad
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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

Cheapest flights from Illinois to Trinidad
Explore the most affordable flight options available from Illinois to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 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.
Fri 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 9/14$423
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.
Sat 11/224:05 pmSTL - POS
1 stop31h 05mAir Canada
Fri 11/282:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 9/16$433
This Air Canada deal was found by Cheapflights users on 9/16. 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.
Fri 9/193:50 pmORD - POS
1 stop8h 30mAir Canada
Sun 9/282:25 amPOS - ORD
1 stop18h 04mAir Canada
Deal found 9/16$433
This Air Canada deal was found by Cheapflights users on 9/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/207:15 amORD - POS
2 stops15h 55mAir Canada
Fri 11/282:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 9/17$438
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/87:43 pmORD - POS
1 stop23h 17mMultiple Airlines
Wed 10/152:40 pmPOS - ORD
2 stops19h 42mMultiple Airlines
Deal found 9/17$452
This Air Canada deal was found by Cheapflights users on 9/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Thu 11/272:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 9/17$473
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:43 pmORD - POS
1 stop23h 17mMultiple Airlines
Mon 10/133:51 amPOS - ORD
2 stops20h 54mMultiple Airlines
Deal found 9/17$475
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.
Sat 11/224:05 pmSTL - POS
1 stop31h 05mAir Canada
Thu 11/272:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 9/16$483
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:25 pmORD - POS
1 stop27h 55mAir Canada
Mon 10/132:25 amPOS - ORD
1 stop16h 08mAir Canada
Deal found 9/17$483
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.
Wed 10/86:40 amORD - POS
1 stop13h 40mMultiple Airlines
Fri 10/103:51 amPOS - ORD
2 stops20h 54mMultiple Airlines
Deal found 9/16$487
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.
Thu 11/204:05 pmSTL - POS
1 stop31h 05mAir Canada
Thu 11/272:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 9/16$533
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/3010:57 amSTL - POS
1 stop8h 03mMultiple Airlines
Thu 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 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 September 17, 2025.
Use the filters below to find and compare flights from Illinois to Trinidad that are best for you.

Fly from

Illinois

Fly to

Trinidad

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-1:01 pm

1 stop12h 46m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 2/2

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Sun 2/8

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-1:01 pm

1 stop12h 46m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Thu 2/5

2:15 am-6:55 pm

2 stops42h 40m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/8

7:43 pm-8:00 pm

1 stop23h 17m

Port of Spain Piarco Intl

Tue 10/14

3:51 am-11:45 pm

2 stops20h 54m

$463

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 10/9

7:43 pm-8:00 pm

1 stop23h 17m

Port of Spain Piarco Intl

Mon 10/13

3:51 am-11:45 pm

2 stops20h 54m

$475

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 11/22

4:05 pm-1:10 am

1 stop31h 05m

Port of Spain Piarco Intl

Tue 11/25

2:15 am-3:29 pm

1 stop15h 14m

$483

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Thu 11/20

4:05 pm-1:10 am

1 stop31h 05m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:29 pm

1 stop15h 14m

$483

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Thu 11/20

4:05 pm-1:10 am

1 stop31h 05m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-3:29 pm

1 stop15h 14m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 30 results
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Best time to book a flight from Illinois to Trinidad

Have a flexible travel schedule? Discover the best time to fly to Trinidad 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

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

Currently, October is the cheapest month in which you can book a flight from Illinois to Trinidad (average of $435). Flying from Illinois to Trinidad 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 LAZ?

Find hourly flight availability from Illinois to Trinidad. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 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 as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Trinidad. 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?

    For as low as $423, Air Canada can have you in Trinidad from Illinois in 9h 10m. There are 2697 mi between Illinois and Trinidad. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois to Trinidad 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?

    Currently, October is the cheapest month in which you can book a flight from Illinois to Trinidad (average of $435). Flying from Illinois to Trinidad 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

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Alternative routes for Illinois to Trinidad

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Port of Spain flights
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O'Hare Intl to Port of Spain flights
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Miami to Scarborough flights
Fort Lauderdale to Scarborough flights
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Atlanta to Scarborough flights
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Orlando to Scarborough flights
San Diego to Port of Spain flights
Pittsburgh to Port of Spain flights
Charleston to Port of Spain flights
Reagan-National to Scarborough flights
Dulles Intl to Scarborough flights
Indianapolis to Port of Spain flights
White Plains to Port of Spain flights

Top 3 airlines flying from Illinois to Trinidad

Discover the top 3 airlines that operate flights from Illinois to Trinidad. 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 September 17, 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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