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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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Illinois to Trinidad and Tobago

Best flights from Illinois to Trinidad and Tobago
Discover carefully curated flight deals from Illinois to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 1, 2026.

This Air Canada deal was found by Cheapflights users on 12/29. 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.
Mon 3/234:05 pmSTL - POS
1 stop31h 15mAir Canada
Thu 3/261:20 amPOS - STL
1 stop15h 09mAir Canada
Deal found 12/29$423
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Fri 3/67:20 amORD - TAB
2 stops12h 20mMultiple Airlines
Wed 3/1112:25 amTAB - ORD
1 stop19h 04mMultiple Airlines
Deal found 12/30$615
This American Airlines deal was found by Cheapflights users on 12/30. 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.
Sat 2/216:53 pmSTL - POS
2 stops18h 13mAmerican Airlines
Sat 2/284:06 pmPOS - STL
1 stop20h 26mAmerican Airlines
Deal found 12/30$626
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Fri 6/198:00 amSTL - POS
2 stops14h 23mUnited Airlines
Fri 6/2612:30 amPOS - STL
2 stops14h 48mUnited Airlines
Deal found 12/30$713
This Air Canada deal was found by Cheapflights users on 12/30. 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.
Mon 1/268:45 pmORD - POS
1 stop26h 35mAir Canada
Sun 2/12:20 amPOS - ORD
2 stops18h 35mAir Canada
Deal found 12/30$423
This Priceline deal was found by Cheapflights users on 12/30. 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.
Sat 1/178:40 pmORD - POS
1 stop26h 40mAir Canada
Fri 1/232:20 amPOS - ORD
1 stop14h 50mAir Canada
Deal found 12/30$423
This Air Canada deal was found by Cheapflights users on 12/30. 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 4/232:00 pmORD - POS
1 stop9h 20mAir Canada
Sun 4/261:20 amPOS - ORD
2 stops18h 33mAir Canada
Deal found 12/30$423
This Air Canada deal was found by Cheapflights users on 12/30. 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.
Mon 1/126:00 pmORD - POS
2 stops29h 20mAir Canada
Thu 1/152:20 amPOS - ORD
2 stops18h 35mAir Canada
Deal found 12/30$423
This Air Canada deal was found by Cheapflights users on 12/31. 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 3/1210:00 amORD - POS
1 stop13h 20mAir Canada
Tue 3/171:20 amPOS - ORD
2 stops18h 32mAir Canada
Deal found 12/31$453
This American Airlines deal was found by Cheapflights users on 12/30. 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.
Fri 6/195:02 amSTL - POS
1 stop16h 45mAmerican Airlines
Sat 6/277:00 amPOS - STL
1 stop16h 45mAmerican Airlines
Deal found 12/30$714
This United Airlines deal was found by Cheapflights users on 12/29. 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.
Mon 3/237:00 pmSTL - POS
2 stops27h 23mUnited Airlines
Thu 3/2612:30 amPOS - STL
2 stops35h 06mUnited Airlines
Deal found 12/29$751
This Air Canada deal was found by Cheapflights users on 12/30. 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 2/214:05 pmSTL - POS
1 stop31h 15mAir Canada
Fri 2/272:20 amPOS - STL
1 stop15h 09mAir Canada
Deal found 12/30$473
This Mytrip deal was found by Cheapflights users on 12/29. 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.
Fri 2/135:15 amORD - TAB
2 stops16h 40mMultiple Airlines
Fri 2/2010:20 pmTAB - ORD
3 stops27h 27mMultiple Airlines
Deal found 12/29$1,502

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 January 1, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$402
(Expedia)

One-way from

$188
(Priceline)

Popular in

December

Cheapest in

October
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. 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

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 January 1, 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

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Mon 3/23

4:05 pm-12:20 am

1 stop31h 15m

Port of Spain Piarco Intl

Thu 3/26

1:20 am-3:29 pm

1 stop15h 09m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/26

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 2/1

2:20 am-6:55 pm

2 stops18h 35m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/17

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 1/23

2:20 am-3:10 pm

1 stop14h 50m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 4/23

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Sun 4/26

1:20 am-6:53 pm

2 stops18h 33m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/12

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Thu 1/15

2:20 am-6:55 pm

2 stops18h 35m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$453

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/21

4:05 pm-1:20 am

1 stop31h 15m

Port of Spain Piarco Intl

Fri 2/27

2:20 am-3:29 pm

1 stop15h 09m

$473

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 3/6

7:20 am-9:40 pm

2 stops12h 20m

Scarborough ANR Robinson Intl

Wed 3/11

12:25 am-6:29 pm

1 stop19h 04m

$615

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/21

6:53 pm-3:06 pm

2 stops18h 13m

Port of Spain Piarco Intl

Sat 2/28

4:06 pm-10:32 am

1 stop20h 26m

$626

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Fri 6/19

8:00 am-11:23 pm

2 stops14h 23m

Port of Spain Piarco Intl

Fri 6/26

12:30 am-2:18 pm

2 stops14h 48m

$713

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 15 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 $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.

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 31h 15m. Air Canada provides one of the quickest options available for as low as $423. The distance between Illinois and Trinidad and Tobago is about 2641 mi.

  • 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 $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 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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$637FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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