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Trinidad and Tobago

$178+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$439
(Kiwi.com)

One-way from

$178
(Trip.com)

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 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. 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 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 noviembre 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/87:10 amORD - POS
1 stop10h 50mMultiple Airlines
vie. 12/129:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 11/6$439
This Air Canada deal was found by Cheapflights users on 11/5. 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.
jue. 11/2012:50 pmORD - POS
2 stops34h 20mAir Canada
jue. 11/272:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/5$443
This Air Canada deal was found by Cheapflights users on 11/5. 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.
sáb. 11/228:15 pmORD - POS
1 stop26h 55mAir Canada
vie. 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/5$483
This Mytrip deal was found by Cheapflights users on 11/5. 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.
sáb. 11/228:15 pmORD - POS
1 stop26h 55mMultiple Airlines
jue. 11/2710:10 amPOS - ORD
1 stop12h 17mMultiple Airlines
Deal found 11/5$528
This Air Canada deal was found by Cheapflights users on 11/5. 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.
jue. 11/208:00 amORD - POS
1 stop15h 10mAir Canada
vie. 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/5$543
This United Airlines deal was found by Cheapflights users on 11/5. 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.
vie. 12/56:15 amSTL - POS
1 stop16h 08mUnited Airlines
jue. 12/111:30 amPOS - STL
1 stop10h 34mUnited Airlines
Deal found 11/5$579
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
dom. 11/166:21 pmSTL - POS
1 stop23h 39mMultiple Airlines
lun. 11/2410:10 amPOS - STL
2 stops30h 19mMultiple Airlines
Deal found 11/4$635
This American Airlines deal was found by Cheapflights users on 11/5. 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.
vie. 12/55:10 amSTL - POS
1 stop16h 49mAmerican Airlines
vie. 12/127:10 amPOS - STL
1 stop18h 49mAmerican Airlines
Deal found 11/5$649
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
dom. 11/166:21 pmSTL - POS
1 stop23h 39mMultiple Airlines
sáb. 11/2212:10 amPOS - STL
2 stops25h 47mMultiple Airlines
Deal found 11/4$712
This United Airlines deal was found by Cheapflights users on 11/4. 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.
dom. 11/1611:20 amSTL - POS
1 stop11h 03mUnited Airlines
dom. 11/231:30 amPOS - STL
1 stop11h 09mUnited Airlines
Deal found 11/4$784
This United Airlines deal was found by Cheapflights users on 11/4. 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.
dom. 11/1611:20 amSTL - POS
1 stop11h 03mUnited Airlines
sáb. 11/221:30 amPOS - STL
1 stop16h 20mUnited Airlines
Deal found 11/4$804
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/165:15 amSTL - POS
1 stop16h 24mAmerican Airlines
lun. 11/247:19 amPOS - STL
1 stop17h 15mAmerican Airlines
Deal found 11/6$824

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 noviembre 6, 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

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 3/13

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

mié. 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 3/12

8:34 am-1:46 am

1 stop16h 12m

Port of Spain Piarco Intl

mié. 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 3/14

12:46 pm-11:23 pm

1 stop9h 37m

Port of Spain Piarco Intl

vie. 3/20

12:30 am-10:07 am

1 stop10h 37m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 3/12

7:20 pm-1:51 pm

2 stops17h 31m

Port of Spain Piarco Intl

mié. 3/18

3:34 pm-12:14 am

1 stop9h 40m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

vie. 11/28

2:15 am-3:10 pm

1 stop14h 55m

$583

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

vie. 12/5

10:00 am-12:23 am

2 stops12h 23m

Port of Spain Piarco Intl

jue. 12/11

1:30 am-10:04 am

1 stop10h 34m

$583

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 3/15

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

sáb. 3/21

3:46 am-1:31 pm

1 stop10h 45m

$595

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 3/15

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

vie. 3/20

3:46 am-1:31 pm

1 stop10h 45m

$598

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 4/6

8:35 am-1:44 am

1 stop16h 09m

Port of Spain Piarco Intl

sáb. 4/11

2:16 pm-1:24 am

1 stop12h 08m

$598

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

vie. 12/5

5:10 am-11:59 pm

1 stop16h 49m

Port of Spain Piarco Intl

vie. 12/12

7:10 am-11:59 pm

1 stop18h 49m

$649

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 20 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 $436). Flying from Illinois to Trinidad and Tobago 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 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 noviembre 6, 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 9h 24m. Copa Airlines provides one of the quickest options available for as low as $527. The distance between Illinois and Trinidad and Tobago is about 2697 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 $436). Flying from Illinois to Trinidad and Tobago 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 noviembre 6, 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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