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Trinidad and Tobago

$182+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$371
(Expedia)

One-way from

$182
(Kiwi.com)

Popular in

December

Cheapest in

October
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 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. 36% potential increase in price ($449 potential increase over avg. RT price).
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Cheapest flight prices on average. 17% potential price decrease ($116 potential savings vs. average RT price).
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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 January 8, 2026.

This Expedia deal was found by Cheapflights users on 1/7. 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.
Thu 3/510:00 amORD - POS
2 stops19h 17mJetBlue
Mon 3/98:05 amPOS - ORD
2 stops26h 04mJetBlue
Deal found 1/7$371
This Air Canada deal was found by Cheapflights users on 1/8. 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
1 stop12h 41mAir Canada
Deal found 1/8$417
This Air Canada deal was found by Cheapflights users on 1/6. 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 1/6$427
This Air Canada deal was found by Cheapflights users on 1/6. 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.
Wed 1/218:45 pmORD - POS
1 stop26h 35mAir Canada
Fri 1/232:20 amPOS - ORD
1 stop19h 25mAir Canada
Deal found 1/6$427
This Air Canada deal was found by Cheapflights users on 1/7. 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 1/108:30 pmORD - POS
1 stop26h 50mAir Canada
Tue 1/132:20 amPOS - ORD
2 stops14h 35mAir Canada
Deal found 1/7$436
This Expedia deal was found by Cheapflights users on 1/7. 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.
Sun 1/258:00 amORD - POS
1 stop15h 20mMultiple Airlines
Sun 2/18:20 amPOS - ORD
2 stops35h 23mMultiple Airlines
Deal found 1/7$440
This Expedia deal was found by Cheapflights users on 1/7. 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.
Sun 1/257:45 amORD - POS
2 stops33h 26mJetBlue
Sun 2/18:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 1/7$444
This FlightHub deal was found by Cheapflights users on 1/6. 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.
Sun 3/228:00 amORD - POS
1 stop15h 20mMultiple Airlines
Mon 3/233:26 pmPOS - ORD
2 stops19h 39mMultiple Airlines
Deal found 1/6$446
This Air Canada deal was found by Cheapflights users on 1/7. 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
1 stop12h 41mAir Canada
Deal found 1/7$447
This United Airlines deal was found by Cheapflights users on 1/8. 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.
Sun 2/227:41 amSTL - POS
2 stops15h 24mUnited Airlines
Sat 2/281:30 amPOS - STL
1 stop9h 53mUnited Airlines
Deal found 1/8$580
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Sun 2/224:13 pmSTL - POS
2 stops20h 53mAmerican Airlines
Sun 3/14:06 pmPOS - STL
2 stops22h 27mAmerican Airlines
Deal found 1/8$609
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/45:53 pmORD - TAB
1 stop17h 07mMultiple Airlines
Wed 2/1110:20 pmTAB - ORD
2 stops27h 04mMultiple Airlines
Deal found 1/7$719

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 8, 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

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-1:01 pm

1 stop12h 41m

$417

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/21

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 3/27

1:20 am-2:55 pm

2 stops14h 35m

$421

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

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/21

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 1/23

2:20 am-7:45 pm

1 stop19h 25m

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 1/25

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 1/25

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$444

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/22

8:00 am-12:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Mon 3/23

3:26 pm-10:05 am

2 stops19h 39m

$446

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-3:10 pm

1 stop14h 50m

$447

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$451

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sun 2/22

10:10 am-12:23 am

1 stop12h 13m

Port of Spain Piarco Intl

Sat 2/28

2:20 am-10:58 am

1 stop10h 38m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 25 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 12h 13m. Air Canada provides one of the quickest options available for as low as $580. The distance between Illinois and Trinidad and Tobago is about 2641 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, 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 8, 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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