Trinidad and Tobago

$248+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jun 21 — Jun 281
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Cheap 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 May 22, 2026.

This Gotogate deal was found by Cheapflights users on 5/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:35 pm
ORD
-
POS
1 stop26h 40m
Air Canada
Sun 5/311:25 am
POS
-
ORD
1 stop16h 34m
Air Canada
Deal found 5/20$520
This Expedia deal was found by Cheapflights users on 5/18. 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.
Sat 6/138:20 pm
ORD
-
POS
1 stop26h 55m
Air Canada
Fri 6/191:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Deal found 5/18$537
This Air Canada deal was found by Cheapflights users on 5/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:40 pm
ORD
-
POS
1 stop26h 35m
Air Canada
Sun 9/201:20 am
POS
-
ORD
1 stop14h 35m
Air Canada
Deal found 5/21$548
This Air Canada deal was found by Cheapflights users on 5/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:50 am
ORD
-
POS
1 stop13h 25m
Air Canada
Mon 9/211:20 am
POS
-
ORD
2 stops18h 23m
Air Canada
Deal found 5/21$551
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:45 am
ORD
-
POS
1 stop11h 15m
Multiple Airlines
Wed 9/239:10 am
POS
-
ORD
2 stops37h 24m
Multiple Airlines
Deal found 5/21$553
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:45 am
ORD
-
POS
1 stop11h 15m
Multiple Airlines
Sun 9/209:10 am
POS
-
ORD
2 stops37h 24m
Multiple Airlines
Deal found 5/21$566
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:45 am
ORD
-
POS
1 stop11h 15m
Multiple Airlines
Thu 9/2410:10 am
POS
-
ORD
1 stop30h 16m
Multiple Airlines
Deal found 5/21$568
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:35 am
STL
-
POS
1 stop13h 48m
United Airlines
Thu 10/112:30 am
POS
-
STL
1 stop10h 40m
United Airlines
Deal found 5/17$830
This Mytrip deal was found by Cheapflights users on 5/18. 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.
Thu 7/28:40 pm
ORD
-
TAB
3 stops24h 35m
Multiple Airlines
Thu 7/96:55 am
TAB
-
ORD
2 stops27h 05m
Multiple Airlines
Deal found 5/18$1,218

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 May 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$537
(Expedia)

One-way from

$248
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$498
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
From Illinois to Trinidad and Tobago
One-way flight from Illinois to Trinidad and Tobago
Highest demand for flights based on searches. 37% potential increase in price ($405 potential increase over avg. RT price).
Cheapest flight prices on average. 16% potential price decrease ($94 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 22, 2026.
Use the filters below to find and compare flights from Illinois to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-1:22 pm

1 stop12h 57m

$574

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 7/15

8:02 am-1:46 am

1 stop16h 44m

Port of Spain Piarco Intl

Tue 7/21

3:50 am-4:00 am

1 stop25h 10m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 6/18

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Sun 6/21

7:45 pm-8:45 am

1 stop14h 00m

$651
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 6/16

10:30 am-11:23 pm

1 stop11h 53m

Port of Spain Piarco Intl

Fri 7/3

2:00 am-12:06 pm

1 stop11h 06m

$675

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/4

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Wed 8/12

7:41 pm-8:48 am

1 stop14h 07m

$679

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Wed 6/17

7:40 pm-8:45 am

1 stop14h 05m

$693

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 6/15

8:00 am-11:00 pm

2 stops14h 00m

Port of Spain Piarco Intl

Fri 7/17

7:00 am-10:00 pm

2 stops16h 00m

$699

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 7/4

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Wed 7/8

7:41 pm-8:48 am

1 stop14h 07m

$700

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/4

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Sun 8/9

7:41 pm-8:48 am

1 stop14h 07m

$719

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/14

10:42 am-12:23 am

1 stop11h 41m

Port of Spain Piarco Intl

Mon 11/16

1:30 am-5:05 pm

1 stop17h 35m

$750

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 20 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $317). Flying from Illinois to Trinidad and Tobago in January is currently the most expensive (average of $638). 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 15h 03m. Air Canada provides one of the quickest options available for as low as $634. 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, June is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $317). Flying from Illinois to Trinidad and Tobago in January is currently the most expensive (average of $638). 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.

Top 4 airlines flying from Illinois to Trinidad and Tobago

Discover the top 4 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 May 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$392Average$526FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$472Average$627FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$548Average$706FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$649FlexibilityNo cancel feeOn-time69%

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