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Trinidad

$193+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$424
(Trip.com)

One-way from

$193
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$621
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
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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. 16% potential increase in price ($134 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($71 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This Trip.com deal was found by Cheapflights users on 11/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:10 amORD - POS
1 stop10h 50mMultiple Airlines
Fri 12/1210:10 amPOS - ORD
1 stop15h 59mMultiple Airlines
Deal found 11/3$424
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Wed 12/38:15 pmORD - POS
1 stop26h 55mMultiple Airlines
Thu 12/119:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 11/2$455
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/123:26 pmORD - POS
1 stop26h 34mMultiple Airlines
Tue 11/183:35 pmPOS - ORD
2 stops23h 10mMultiple Airlines
Deal found 11/2$477
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Mon 11/175:10 amORD - POS
1 stop12h 50mMultiple Airlines
Wed 12/35:55 pmPOS - ORD
2 stops25h 32mMultiple Airlines
Deal found 11/2$481
This Air Canada deal was found by Cheapflights users on 11/2. 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.
Sat 11/228:15 pmORD - POS
1 stop26h 55mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/2$483
This Air Canada deal was found by Cheapflights users on 11/2. 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 11/216:05 pmORD - POS
2 stops53h 05mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 11/2$493
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Sat 11/88:15 pmORD - POS
1 stop26h 55mMultiple Airlines
Thu 11/1310:10 amPOS - ORD
1 stop16h 17mMultiple Airlines
Deal found 11/2$506
This Priceline deal was found by Cheapflights users on 11/2. 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.
Mon 11/176:45 amORD - POS
1 stop30h 22mJetBlue
Wed 12/35:42 pmPOS - ORD
1 stop30h 10mJetBlue
Deal found 11/2$511

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 November 3, 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

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-1:01 pm

1 stop12h 46m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 11/17

5:10 am-8:00 pm

1 stop12h 50m

Port of Spain Piarco Intl

Tue 12/2

2:15 am-2:55 pm

2 stops14h 40m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 12/8

7:10 am-8:00 pm

1 stop10h 50m

Port of Spain Piarco Intl

Thu 12/11

12:10 am-2:57 pm

1 stop16h 47m

$525

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Wed 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Wed 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

7:35 am-11:23 pm

1 stop14h 48m

Port of Spain Piarco Intl

Tue 3/17

12:30 am-5:08 pm

1 stop17h 38m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 12/8

10:35 am-12:23 am

1 stop11h 48m

Port of Spain Piarco Intl

Thu 12/11

1:30 am-11:11 am

1 stop11h 41m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/3

7:33 am-1:48 am

1 stop16h 15m

Port of Spain Piarco Intl

Wed 12/10

3:47 am-12:52 pm

1 stop11h 05m

$550

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/7

6:00 am-12:23 am

1 stop16h 23m

Port of Spain Piarco Intl

Tue 2/10

1:30 am-9:22 am

1 stop9h 52m

$689

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/3

6:35 pm-3:46 pm

2 stops19h 11m

Port of Spain Piarco Intl

Sat 1/17

6:30 am-10:59 pm

2 stops18h 29m

$738

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 20 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, November is the cheapest month in which you can book a flight from Illinois to Trinidad (average of $436). Flying from Illinois to Trinidad in July is currently the most expensive (average of $613). 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 November 3, 2025.

It’s typically best to fly out from Illinois to Trinidad in the morning. Doing so could potentially save you 36% on the flight price compared to flying in the evening, which is usually more expensive.

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 $527, Air Canada can have you in Trinidad from Illinois in 9h 24m. 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, November is the cheapest month in which you can book a flight from Illinois to Trinidad (average of $436). Flying from Illinois to Trinidad in July is currently the most expensive (average of $613). 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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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$487Average$556FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$560Average$628FlexibilityNo cancel feeOn-time69%

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