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

$193+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$427
(Kiwi.com)

One-way from

$193
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$621
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. 16% potential increase in price ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($71 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 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/211:40 amORD - POS
1 stop29h 15mMultiple Airlines
Tue 12/98:55 amPOS - ORD
1 stop32h 02mMultiple Airlines
Deal found 11/1$427
This Air Canada deal was found by Cheapflights users on 11/1. 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.
Thu 11/206:05 pmORD - POS
2 stops29h 05mAir Canada
Sun 11/302:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 11/1$443
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Mon 12/87:41 pmORD - POS
1 stop21h 14mMultiple Airlines
Fri 12/1210:10 amPOS - ORD
1 stop26h 58mMultiple Airlines
Deal found 10/31$448
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/77:10 amORD - POS
1 stop10h 50mMultiple Airlines
Fri 12/1210:10 amPOS - ORD
1 stop26h 58mMultiple Airlines
Deal found 10/31$458
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:26 pmORD - POS
1 stop26h 34mMultiple Airlines
Tue 11/183:35 pmPOS - ORD
2 stops23h 10mMultiple Airlines
Deal found 11/2$477
This Air Canada deal was found by Cheapflights users on 11/2. 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.
Sat 11/228:15 pmORD - POS
1 stop26h 55mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/2$483
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/205:00 amORD - POS
1 stop13h 00mMultiple Airlines
Mon 12/12:38 pmPOS - ORD
2 stops45h 57mMultiple Airlines
Deal found 10/30$488

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 3, 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

Thu 11/20

12:50 pm-1:10 am

2 stops34h 20m

Port of Spain Piarco Intl

Sun 11/30

2:15 am-6:55 pm

2 stops18h 40m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/27

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-8:00 am

2 stops55h 45m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 11/12

3:26 pm-8:00 pm

1 stop26h 34m

Port of Spain Piarco Intl

Tue 11/18

3:35 pm-12:45 pm

2 stops23h 10m

$477

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

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

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/19

8:34 am-1:46 am

1 stop16h 12m

Port of Spain Piarco Intl

Fri 3/27

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

7:35 am-1:44 am

1 stop16h 09m

Port of Spain Piarco Intl

Mon 1/19

3:40 am-12:46 pm

1 stop11h 06m

$527

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

Tue 3/17

3:46 am-1:31 pm

1 stop10h 45m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 12/25

2:07 pm-1:48 am

1 stop9h 41m

Port of Spain Piarco Intl

Sat 3/7

3:46 am-12:31 pm

1 stop10h 45m

$527

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/3

6:35 pm-3:46 pm

2 stops19h 11m

Port of Spain Piarco Intl

Sat 1/17

6:30 am-10:59 pm

2 stops18h 29m

$738

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 19 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 $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 November 3, 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. Air Canada 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.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
Orlando to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
John F Kennedy Intl to Santo Domingo flights
Dulles Intl to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Baltimore to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Newark to Oranjestad flights
John F Kennedy Intl to Montego Bay flights
Boston to Oranjestad flights
LaGuardia to Punta Cana flights
Hartford to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
Newark to Montego Bay flights
Tampa to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
John F Kennedy Intl to Port of Spain flights
Raleigh to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
Newark to Nassau flights
O'Hare Intl to Punta Cana flights
Minneapolis to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island flights
George Bush Intcntl to Luis Munoz Marin Intl flights
LaGuardia to Oranjestad flights
Dulles Intl to Punta Cana flights
John F Kennedy Intl to Nassau flights
Miami to Santo Domingo flights
Fort Lauderdale to Santo Domingo flights
John F Kennedy Intl to Simpson Bay flights
John F Kennedy Intl to Kingston flights
Detroit to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
Orlando to Punta Cana flights
LaGuardia to Montego Bay flights
John F Kennedy Intl to Saint Thomas Island 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$487Average$556FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$560Average$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.