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Trinidad

$189+ Cheap flights from Illinois to Trinidad

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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap flight deals from Illinois to Trinidad

Cheapest flights from Illinois to Trinidad
Explore the most affordable flight options available from Illinois to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.

This Air Canada deal was found by Cheapflights users on 2/3. 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 3/308:20 pm
ORD
-
POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/3$358
This Air Canada deal was found by Cheapflights users on 2/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:40 pm
ORD
-
POS
1 stop26h 40m
Air Canada
Fri 2/272:20 am
POS
-
ORD
2 stops18h 32m
Air Canada
Deal found 2/4$363
This Air Canada deal was found by Cheapflights users on 2/3. 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.
Fri 2/278:00 am
ORD
-
POS
1 stop15h 20m
Air Canada
Thu 3/52:20 am
POS
-
ORD
1 stop17h 28m
Air Canada
Deal found 2/3$368
This Travelocity deal was found by Cheapflights users on 2/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/297:13 am
ORD
-
POS
2 stops16h 07m
Air Canada
Fri 4/31:20 am
POS
-
ORD
2 stops31h 40m
Air Canada
Deal found 2/1$375
This Air Canada deal was found by Cheapflights users on 2/3. 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 4/29:50 am
ORD
-
POS
1 stop13h 30m
Air Canada
Fri 4/101:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/3$383
This Air Canada deal was found by Cheapflights users on 2/2. 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 3/1510:00 am
ORD
-
POS
1 stop13h 20m
Air Canada
Tue 3/171:20 am
POS
-
ORD
2 stops18h 32m
Air Canada
Deal found 2/2$398
This Air Canada deal was found by Cheapflights users on 2/5. 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.
Fri 3/271:55 pm
ORD
-
POS
1 stop9h 25m
Air Canada
Thu 4/21:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/5$408
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 3/3110:10 am
STL
-
POS
1 stop12h 13m
United Airlines
Sat 4/412:30 am
POS
-
STL
1 stop9h 55m
United Airlines
Deal found 2/2$600
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Sat 10/311:00 am
STL
-
POS
1 stop11h 23m
United Airlines
Fri 10/912:30 am
POS
-
STL
1 stop17h 05m
United Airlines
Deal found 2/4$620
This Mytrip deal was found by Cheapflights users on 2/3. 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.
Sat 2/214:05 pm
STL
-
POS
1 stop31h 15m
Air Canada
Fri 2/272:20 am
POS
-
STL
2 stops20h 06m
Air Canada
Deal found 2/3$681
This Air Canada deal was found by Cheapflights users on 2/1. 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 pm
STL
-
POS
1 stop31h 15m
Air Canada
Thu 3/261:20 am
POS
-
STL
1 stop15h 09m
Air Canada
Deal found 2/1$688
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 3/316:20 pm
STL
-
POS
1 stop18h 50m
American Airlines
Sun 4/53:10 pm
POS
-
STL
1 stop20h 22m
American Airlines
Deal found 2/2$708

Find flight deals from Illinois to Trinidad

Keep the following information in mind while searching for Illinois to Trinidad flight deals. Data was last updated February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Air Canada)

One-way from

$189
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$902
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
Search Deals
One-way flight from Illinois to Trinidad
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($449 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 17% potential price decrease ($117 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Trinidad 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 February 5, 2026.
Use the filters below to find and compare flights from Illinois to Trinidad that are best for you.

Fly from

Illinois

Fly to

Trinidad

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-1:05 pm

1 stop12h 45m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/29

8:40 am-12:20 am

2 stops14h 40m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-1:05 pm

1 stop12h 45m

$361

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 2/21

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 2/27

2:20 am-6:52 pm

2 stops18h 32m

$363

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/27

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Thu 3/5

2:20 am-5:48 pm

1 stop17h 28m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

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

$398

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Tue 3/31

10:10 am-11:23 pm

1 stop12h 13m

Port of Spain Piarco Intl

Sat 4/4

12:30 am-9:25 am

1 stop9h 55m

$600

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-9:05 pm

2 stops20h 45m

$681

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

$688

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Tue 3/31

6:20 pm-2:10 pm

1 stop18h 50m

Port of Spain Piarco Intl

Sun 4/5

3:10 pm-10:32 am

1 stop20h 22m

$708

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 19 results
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Best time to book a flight from Illinois to Trinidad

Have a flexible travel schedule? Discover the best time to fly to Trinidad 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

What is the cheapest month to book a flight from Illinois to Trinidad?

Currently, November is the cheapest month in which you can book a flight from Illinois to Trinidad (average of $435). Flying from Illinois to Trinidad 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. 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?

    For as low as $600, Air Canada can have you in Trinidad from Illinois in 12h 13m. There are 2641 mi between Illinois and Trinidad. This flight may include one or multiple stops.

  • Can I find deals for flights from Illinois to Trinidad that include hotel bookings?

    Yes. In addition to deals on Illinois to Trinidad flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Trinidad?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Trinidad.

  • Can I find deals for business class flights from Illinois to Trinidad?

    Yes. Cheapflights offers flight deals from Illinois to Trinidad 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?

    Currently, November is the cheapest month in which you can book a flight from Illinois to Trinidad (average of $435). Flying from Illinois to Trinidad 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Trinidad

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Port of Spain flights
Newark to Port of Spain flights
LaGuardia to Port of Spain flights
Miami to Port of Spain flights
Atlanta to Port of Spain flights
Dulles Intl to Port of Spain flights
Reagan-National to Port of Spain flights
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Fort Lauderdale to Port of Spain flights
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O'Hare Intl to Port of Spain flights
John F Kennedy Intl to Scarborough flights
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Minneapolis to Port of Spain flights
New Orleans to Port of Spain flights
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Indianapolis to Port of Spain flights
Miami to Scarborough flights
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Charlotte to Port of Spain flights
Newark to Scarborough flights
Austin to Port of Spain flights
Nashville to Port of Spain flights
Jacksonville to Port of Spain flights
Pittsburgh to Port of Spain flights
San Diego to Port of Spain flights
Charleston to Port of Spain flights
Denver to Port of Spain flights
Providence to Port of Spain flights
Fort Lauderdale to Scarborough flights
Madison to Port of Spain flights
St. Louis to Port of Spain flights
Fayetteville to Port of Spain flights
Sacramento to Port of Spain flights
Hartford to Port of Spain flights

Top 3 airlines flying from Illinois to Trinidad

Discover the top 3 airlines that operate flights from Illinois to Trinidad. 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$501Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$528Average$669FlexibilityNo cancel feeOn-time71%

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