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Trinidad

$251+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Copa Airlines deal was found by Cheapflights users on 12/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:33 amORD - POS
1 stop16h 15mCopa Airlines
Wed 12/243:13 amPOS - ORD
1 stop11h 39mCopa Airlines
Deal found 12/17$567
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:41 pmORD - POS
2 stops32h 37mJetBlue
Wed 1/78:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 12/16$759
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Thu 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$765
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Fri 1/99:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$777
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Wed 12/174:38 pmORD - POS
2 stops19h 17mMultiple Airlines
Tue 12/232:15 amPOS - ORD
1 stop14h 55mMultiple Airlines
Deal found 12/16$804
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Wed 1/79:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 12/16$846
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/175:40 amORD - POS
2 stops12h 40mMultiple Airlines
Thu 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$867
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/246:35 pmSTL - POS
2 stops27h 48mUnited Airlines
Tue 12/301:30 amPOS - STL
2 stops23h 13mUnited Airlines
Deal found 12/16$898
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/244:27 pmSTL - POS
2 stops31h 21mMultiple Airlines
Wed 12/318:30 amPOS - STL
1 stop16h 03mMultiple Airlines
Deal found 12/16$1,054
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:05 amSTL - POS
1 stop8h 39mAmerican Airlines
Wed 12/316:02 amPOS - STL
1 stop18h 33mAmerican Airlines
Deal found 12/16$1,142

Find flight deals from Illinois to Trinidad

Keep the following information in mind while searching for Illinois to Trinidad flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$391
(Trip.com)

One-way from

$251
(Expedia)

Popular in

December

Cheapest in

October

Average price

$1,705
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
Search Deals
One-way flight from Illinois to Trinidad
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($425 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($107 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Thu 1/15

5:15 am-8:00 pm

1 stop12h 45m

Port of Spain Piarco Intl

Thu 1/22

10:10 am-9:03 pm

1 stop12h 53m

$391

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

7:20 am-8:00 pm

1 stop10h 40m

Port of Spain Piarco Intl

Fri 2/6

10:10 am-7:38 pm

1 stop11h 28m

$435

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Thu 2/5

2:20 am-6:55 pm

2 stops18h 35m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/31

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 2/6

2:20 am-1:01 pm

1 stop12h 41m

$453

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

6:04 pm-12:20 am

2 stops29h 16m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:20 pm-12:20 am

2 stops29h 00m

Port of Spain Piarco Intl

Mon 4/6

3:40 pm-9:10 am

2 stops18h 30m

$480

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Wed 2/11

6:00 am-12:23 am

1 stop16h 23m

Port of Spain Piarco Intl

Tue 2/17

1:30 am-3:38 pm

1 stop16h 08m

$1,669

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Wed 2/11

6:02 pm-4:58 pm

1 stop20h 56m

Port of Spain Piarco Intl

Wed 2/18

4:40 pm-10:59 am

2 stops20h 19m

$1,780

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/24

7:41 pm-2:31 pm

2 stops16h 50m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 12 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 $435). Flying from Illinois to Trinidad in April is currently the most expensive (average of $628). 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 December 18, 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 $443, Air Canada can have you in Trinidad from Illinois in 9h 20m. 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 $435). Flying from Illinois to Trinidad in April is currently the most expensive (average of $628). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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