HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad and Tobago

$308+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Trinidad and Tobago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$433
(Air Canada)

One-way from

$308
(Copa Airlines)

Popular in

December

Cheapest in

October

Average price

$578
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 and Tobago
Search Deals
One-way flight from Illinois to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($367 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($99 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 26, 2025.

This Mytrip deal was found by Cheapflights users on 11/25. 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 11/293:55 pmORD - POS
3 stops25h 55mMultiple Airlines
Sun 11/302:15 amPOS - ORD
2 stops38h 40mMultiple Airlines
Deal found 11/25$616
This Copa Airlines deal was found by Cheapflights users on 11/25. 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.
Sat 11/296:56 amORD - POS
1 stop16h 52mCopa Airlines
Sun 11/303:47 amPOS - ORD
1 stop11h 05mCopa Airlines
Deal found 11/25$660
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Fri 12/129:14 pmORD - POS
2 stops19h 41mMultiple Airlines
Wed 12/319:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Deal found 11/25$691
This Mytrip deal was found by Cheapflights users on 11/25. 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.
Wed 11/263:55 pmORD - POS
1 stop31h 15mMultiple Airlines
Sun 11/309:55 pmPOS - ORD
3 stops23h 28mMultiple Airlines
Deal found 11/25$724
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Sat 12/135:40 amORD - POS
2 stops12h 40mMultiple Airlines
Wed 12/319:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Deal found 11/25$729
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Sun 12/1410:24 amORD - POS
2 stops31h 36mMultiple Airlines
Wed 12/319:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Deal found 11/25$730
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Sat 12/207:43 pmSTL - POS
2 stops31h 32mMultiple Airlines
Sun 12/288:30 amPOS - STL
1 stop27h 15mMultiple Airlines
Deal found 11/25$1,025
This United Airlines deal was found by Cheapflights users on 11/25. 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 12/206:35 pmSTL - POS
2 stops27h 48mUnited Airlines
Sat 12/271:30 amPOS - STL
1 stop10h 19mUnited Airlines
Deal found 11/25$1,062
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Sat 12/206:00 pmSTL - POS
1 stop19h 46mAmerican Airlines
Sun 12/286:02 amPOS - STL
1 stop13h 49mAmerican Airlines
Deal found 11/25$1,294

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 26, 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

Wed 1/21

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Fri 1/23

2:20 am-3:10 pm

1 stop14h 50m

$433

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-3:16 pm

1 stop13h 41m

$438

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

$453

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$453

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 5/11

6:15 am-11:23 pm

1 stop16h 08m

Port of Spain Piarco Intl

Thu 5/14

12:30 am-3:04 pm

1 stop15h 34m

$729

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Mon 5/11

10:48 am-2:00 pm

2 stops26h 12m

Port of Spain Piarco Intl

Fri 5/15

3:10 pm-12:05 pm

2 stops21h 55m

$733

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 12/20

7:43 pm-5:15 am

2 stops31h 32m

Port of Spain Piarco Intl

Sun 12/28

8:30 am-9:45 am

1 stop27h 15m

$1,025

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 12/12

2:07 pm-1:48 am

1 stop9h 41m

$308

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 12/12

2:00 pm-8:20 pm

3 stops28h 20m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 16 results
1
2

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 26, 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 29h 20m. 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

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.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Santo Domingo flights
John F Kennedy Intl to Punta Cana flights
Dulles Intl to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
LaGuardia to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Boston to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Atlanta to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
O'Hare Intl to Punta Cana flights
Hartford to Luis Munoz Marin Intl flights
John F Kennedy Intl to Port of Spain flights
LaGuardia to Santo Domingo flights
Tampa to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
Boston to Punta Cana flights
Boston to Oranjestad flights
Dulles Intl to Punta Cana flights
Minneapolis to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
John F Kennedy Intl to Kingston flights
Newark to Nassau flights
Orlando to Punta Cana flights
Detroit to Luis Munoz Marin Intl flights
John F Kennedy Intl to Simpson Bay flights
LaGuardia to Nassau flights
Newark to Montego Bay flights
LaGuardia to Oranjestad flights
Midway to Luis Munoz Marin Intl flights
John F Kennedy Intl to Nassau flights
John F Kennedy Intl to Saint Thomas Island flights
Newark to Simpson Bay flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Miami to Santo Domingo flights
Hobby to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island flights
Fort Lauderdale to Santo Domingo flights

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 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$518Average$621FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.