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Trinidad and Tobago

$198+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Dec 22 — Dec 291
Mon 12/22
Mon 12/29
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 November 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$433
(Air Canada)

One-way from

$198
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$578
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. 33% potential increase in price ($365 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($99 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 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 November 22, 2025.

This Air Canada deal was found by Cheapflights users on 11/19. 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.
Tue 12/27:05 amORD - POS
2 stops16h 05mAir Canada
Fri 12/52:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/19$433
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Mon 12/86:05 pmORD - POS
2 stops29h 05mAir Canada
Thu 12/112:15 amPOS - ORD
2 stops42h 40mAir Canada
Deal found 11/20$493
This Expedia deal was found by Cheapflights users on 11/20. 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.
Mon 12/88:38 pmORD - POS
2 stops17h 26mJetBlue
Thu 12/115:56 pmPOS - ORD
1 stop29h 56mJetBlue
Deal found 11/20$494
This Mytrip deal was found by Cheapflights users on 11/21. 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.
Mon 12/85:00 amORD - POS
1 stop13h 00mMultiple Airlines
Thu 12/1110:10 amPOS - ORD
1 stop11h 51mMultiple Airlines
Deal found 11/21$504
This Expedia deal was found by Cheapflights users on 11/20. 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.
Mon 12/88:38 pmORD - POS
2 stops17h 26mJetBlue
Fri 12/125:42 pmPOS - ORD
1 stop30h 10mJetBlue
Deal found 11/20$518
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Mon 12/87:10 amORD - POS
1 stop10h 50mMultiple Airlines
Fri 12/1210:10 amPOS - ORD
1 stop11h 51mMultiple Airlines
Deal found 11/20$551
This Copa Airlines deal was found by Cheapflights users on 11/21. 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.
Mon 12/87:33 amORD - POS
1 stop16h 15mCopa Airlines
Wed 12/103:47 amPOS - ORD
1 stop11h 05mCopa Airlines
Deal found 11/21$567
This Justfly.com deal was found by Cheapflights users on 11/20. 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 Justfly.com 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
2 stops14h 40mAir Canada
Deal found 11/20$582

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 November 22, 2025.
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

Sat 1/10

4:05 pm-1:20 am

1 stop31h 15m

Port of Spain Piarco Intl

Fri 1/16

2:20 am-3:29 pm

1 stop15h 09m

$438

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Mon 5/11

1:30 pm-1:35 am

2 stops35h 05m

Port of Spain Piarco Intl

Thu 5/14

2:35 am-7:30 pm

1 stop17h 55m

$443

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-1:01 pm

1 stop12h 41m

$463

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-2:55 pm

2 stops14h 35m

$463

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

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Mon 3/16

6:24 pm-1:51 pm

2 stops18h 27m

Port of Spain Piarco Intl

Mon 3/23

3:34 pm-2:48 pm

2 stops24h 14m

$583

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/10

6:30 am-12:23 am

2 stops15h 53m

Port of Spain Piarco Intl

Fri 1/16

1:30 am-3:39 pm

1 stop16h 09m

$599

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/10

10:00 am-10:48 pm

1 stop10h 48m

Port of Spain Piarco Intl

Sat 1/17

6:30 am-11:26 pm

2 stops18h 56m

$613

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/6

2:00 pm-1:20 am

1 stop9h 20m

$198

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/5

8:30 pm-1:20 am

1 stop26h 50m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 17 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.

What is the cheapest time of day to fly from IL to TT?

Find hourly flight availability from Illinois to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 22, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 33% on flights from Illinois to Trinidad and Tobago by exploring options for tickets in the afternoon.

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 16h 05m. Air Canada provides one of the quickest options available for as low as $433. The distance between Illinois and Trinidad and Tobago is about 2697 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 November 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$487Average$572FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$560Average$628FlexibilityNo cancel feeOn-time69%

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