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Trinidad and Tobago

$290+ 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$302
(Kiwi.com)

One-way from

$290
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$1,342
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
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From Illinois to Trinidad and Tobago
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One-way flight from Illinois to Trinidad and Tobago
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Highest demand for flights based on searches. 22% potential increase in price ($202 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($59 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
mié. 3/268:42 pmORD - POS
1 stop18h 59mMultiple Airlines
jue. 4/176:01 pmPOS - ORD
2 stops21h 25mMultiple Airlines
Deal found 2/19$302
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/199:12 amORD - POS
2 stops30h 29mFrontier
dom. 3/236:01 pmPOS - ORD
2 stops47h 37mFrontier
Deal found 2/20$398
This Copa Airlines deal was found by Cheapflights users on 2/19. 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.
vie. 7/253:07 pmORD - POS
1 stop9h 40mCopa Airlines
mié. 8/132:35 pmPOS - ORD
1 stop10h 47mCopa Airlines
Deal found 2/19$486
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/192:50 pmORD - POS
1 stop22h 15mAmerican Airlines
dom. 3/233:15 pmPOS - ORD
1 stop18h 50mAmerican Airlines
Deal found 2/20$555
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/67:45 amORD - POS
1 stop14h 38mUnited Airlines
sáb. 4/1212:30 amPOS - ORD
1 stop10h 41mUnited Airlines
Deal found 2/20$628
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/64:32 pmORD - TAB
2 stops27h 33mMultiple Airlines
dom. 4/136:55 amTAB - ORD
2 stops29h 03mMultiple Airlines
Deal found 2/20$628

Find flights from Illinois to Trinidad and Tobago within your budget

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 febrero 20, 2025.

Fly from

Illinois

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 3/26

8:42 pm-4:41 pm

1 stop18h 59m

Port of Spain Piarco Intl

jue. 4/17

6:01 pm-2:26 pm

2 stops21h 25m

$302

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 3/19

9:12 am-4:41 pm

2 stops30h 29m

Port of Spain Piarco Intl

dom. 3/23

6:01 pm-4:38 pm

2 stops47h 37m

$398

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 7/25

3:07 pm-1:47 am

1 stop9h 40m

Port of Spain Piarco Intl

mié. 8/13

2:35 pm-12:22 am

1 stop10h 47m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 3/19

2:50 pm-2:05 pm

1 stop22h 15m

Port of Spain Piarco Intl

dom. 3/23

3:15 pm-9:05 am

1 stop18h 50m

$555

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 4/6

9:15 am-11:23 pm

1 stop13h 08m

Port of Spain Piarco Intl

sáb. 4/12

12:30 am-11:31 am

1 stop12h 01m

$628

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

dom. 4/6

4:32 pm-9:05 pm

2 stops27h 33m

Scarborough ANR Robinson Intl

dom. 4/13

6:55 am-10:58 am

2 stops29h 03m

$628

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 3/20

6:25 pm-8:00 pm

2 stops24h 35m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Illinois to Trinidad and Tobago

Get recent, data-driven insights about flights from Illinois to Trinidad and Tobago including ideal travel times, pricing trends, and more.

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 febrero 20, 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.

Rainfall in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Trinidad and Tobago ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Trinidad and Tobago when rainfall is around 1.2 in.

Temperature in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Trinidad and Tobago, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 febrero 20, 2025.
To help decide which airline to fly from Illinois to Trinidad and Tobago, see what other customers have to say about Copa Airlines, United Airlines and American Airlines. 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
7.6
Good
1,510 reviews

Comfort

7.4

Food

6.9

Entertainment

6.9

Overall

7.6

Crew

8.1

Boarding

7.8

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Copa Airlines
7.6
Good
1,510 reviews
Copa Airlines
7.6
Good
1,510 reviews

Comfort

7.4

Food

6.9

Entertainment

6.9

Overall

7.6

Crew

8.1

Boarding

7.8

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

United Airlines
7.4
Good
8,766 reviews
Copa Airlines
7.6
Good
1,510 reviews

Comfort

7.4

Food

6.9

Entertainment

6.9

Overall

7.6

Crew

8.1

Boarding

7.8

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,510 reviews

Comfort

7.4

Food

6.9

Entertainment

6.9

Overall

7.6

Crew

8.1

Boarding

7.8

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Frontier
6.0
Okay
3,355 reviews
Copa Airlines
7.6
Good
1,510 reviews

Comfort

7.4

Food

6.9

Entertainment

6.9

Overall

7.6

Crew

8.1

Boarding

7.8

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

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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Alternative routes for Illinois to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$449Average$596FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$452Average$557FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$478Average$614FlexibilityNo cancel feeOn-time69%
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