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Trinidad and Tobago

$247+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$483
(Kiwi.com)

One-way from

$247
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$847
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. 18% potential increase in price ($165 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($62 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Mon 7/148:09 amORD - POS
1 stop9h 46mMultiple Airlines
Mon 8/253:49 amPOS - ORD
2 stops30h 33mMultiple Airlines
Deal found 6/30$483
This Copa Airlines deal was found by Cheapflights users on 6/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:55 amORD - POS
1 stop16h 51mCopa Airlines
Wed 8/272:38 pmPOS - ORD
1 stop10h 43mCopa Airlines
Deal found 6/30$516
This Air Canada deal was found by Cheapflights users on 6/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1410:40 amORD - POS
2 stops13h 40mAir Canada
Sun 7/202:20 amPOS - ORD
2 stops17h 33mAir Canada
Deal found 6/30$537
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/167:15 pmORD - POS
1 stop18h 01mAmerican Airlines
Fri 9/263:25 pmPOS - ORD
1 stop9h 23mAmerican Airlines
Deal found 6/30$548
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/16:16 amORD - POS
1 stop10h 48mJetBlue
Tue 8/128:50 amPOS - ORD
1 stop14h 38mJetBlue
Deal found 6/30$555
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/145:26 amSTL - POS
1 stop15h 10mAmerican Airlines
Thu 8/213:35 pmPOS - STL
1 stop9h 24mAmerican Airlines
Deal found 6/30$560
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Thu 8/76:00 amORD - POS
1 stop16h 23mUnited Airlines
Sun 8/1012:30 amPOS - ORD
1 stop10h 51mUnited Airlines
Deal found 6/29$600
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/141:30 pmSTL - POS
2 stops34h 50mAir Canada
Sun 8/172:20 amPOS - STL
1 stop18h 25mAir Canada
Deal found 6/30$647
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/148:25 amSTL - POS
1 stop13h 58mUnited Airlines
Wed 8/2012:30 amPOS - STL
1 stop10h 31mUnited Airlines
Deal found 6/30$658
This Mytrip deal was found by Cheapflights users on 6/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:37 amSTL - POS
1 stop8h 23mMultiple Airlines
Sun 8/172:20 amPOS - STL
1 stop18h 25mMultiple Airlines
Deal found 6/30$746
This Trip.com deal was found by Cheapflights users on 7/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/141:07 amORD - TAB
2 stops21h 48mMultiple Airlines
Thu 8/2112:30 amTAB - ORD
2 stops38h 11mMultiple Airlines
Deal found 7/1$753

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 July 1, 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

Mon 7/14

8:09 am-6:55 pm

1 stop9h 46m

Port of Spain Piarco Intl

Mon 8/25

3:49 am-9:22 am

2 stops30h 33m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 8/14

7:55 am-1:46 am

1 stop16h 51m

Port of Spain Piarco Intl

Wed 8/27

2:38 pm-12:21 am

1 stop10h 43m

$516

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/14

10:40 am-1:20 am

2 stops13h 40m

Port of Spain Piarco Intl

Sun 7/20

2:20 am-6:53 pm

2 stops17h 33m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

7:15 pm-2:16 pm

1 stop18h 01m

Port of Spain Piarco Intl

Fri 9/26

3:25 pm-11:48 pm

1 stop9h 23m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 8/1

6:16 am-6:04 pm

1 stop10h 48m

Port of Spain Piarco Intl

Tue 8/12

8:50 am-10:28 pm

1 stop14h 38m

$555

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Thu 8/14

5:26 am-9:36 pm

1 stop15h 10m

Port of Spain Piarco Intl

Thu 8/21

3:35 pm-11:59 pm

1 stop9h 24m

$560

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 8/7

6:00 am-11:23 pm

1 stop16h 23m

Port of Spain Piarco Intl

Sun 8/10

12:30 am-10:21 am

1 stop10h 51m

$600

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Thu 8/14

1:30 pm-1:20 am

2 stops34h 50m

Port of Spain Piarco Intl

Sun 8/17

2:20 am-7:45 pm

1 stop18h 25m

$647

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Thu 8/14

8:25 am-11:23 pm

1 stop13h 58m

Port of Spain Piarco Intl

Wed 8/20

12:30 am-10:01 am

1 stop10h 31m

$658

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Thu 8/14

10:37 am-8:00 pm

1 stop8h 23m

Port of Spain Piarco Intl

Sun 8/17

2:20 am-7:45 pm

1 stop18h 25m

$746

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 13 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, October 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 December is currently the most expensive (average of $710). 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 July 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Trinidad and Tobago as you normally would.

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Trinidad and Tobago. Reviews last updated July 1, 2025.
See what other customers who have flown with Copa Airlines, United Airlines, and JetBlue from Illinois to Trinidad and Tobago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,465 reviews

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Food

6.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,465 reviews
Copa Airlines
7.5
Good
1,465 reviews

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Food

6.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,852 reviews
Copa Airlines
7.5
Good
1,465 reviews

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Food

6.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
JetBlue
7.3
Good
2,920 reviews
Copa Airlines
7.5
Good
1,465 reviews

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Food

6.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,465 reviews

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Food

6.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,657 reviews
Copa Airlines
7.5
Good
1,465 reviews

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Food

6.8

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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.

  • 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, October 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 December is currently the most expensive (average of $710). 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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Top 2 airlines flying from Illinois to Trinidad and Tobago

Discover the top 2 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$615FlexibilityNo cancel feeOn-time71%

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