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Trinidad and Tobago

$207+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$486
(Copa Airlines)

One-way from

$207
(Kiwi.com)

Popular in

February

Cheapest in

January
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
Search Deals
One-way flight from Illinois to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($154 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($61 potential savings vs. average RT price).
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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 April 30, 2025.

This Copa Airlines deal was found by Cheapflights users on 4/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/223:07 pmORD - POS
1 stop9h 41mCopa Airlines
Sun 10/264:01 amPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 4/29$486
This Air Canada deal was found by Cheapflights users on 4/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/103:50 pmORD - POS
1 stop8h 35mAir Canada
Sun 10/122:25 amPOS - ORD
2 stops18h 46mAir Canada
Deal found 4/29$517
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/131:43 pmORD - POS
1 stop28h 12mMultiple Airlines
Fri 6/2010:10 amPOS - ORD
1 stop23h 40mMultiple Airlines
Deal found 4/29$531
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/299:21 amORD - POS
1 stop13h 02mUnited Airlines
Wed 6/412:30 amPOS - ORD
1 stop20h 25mUnited Airlines
Deal found 4/29$538
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/138:21 amORD - POS
1 stop12h 15mAmerican Airlines
Fri 6/207:09 amPOS - ORD
1 stop16h 20mAmerican Airlines
Deal found 4/29$539
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/131:43 pmORD - TAB
2 stops31h 17mMultiple Airlines
Fri 6/207:35 amTAB - ORD
2 stops26h 15mMultiple Airlines
Deal found 4/29$608
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/136:15 amORD - POS
1 stop10h 49mJetBlue
Fri 6/207:29 pmPOS - ORD
1 stop15h 44mJetBlue
Deal found 4/29$698
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 4/304:20 pmSTL - POS
1 stop30h 03mUnited Airlines
Tue 5/612:30 amPOS - STL
1 stop16h 19mUnited Airlines
Deal found 4/29$1,001

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 April 30, 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 10/22

3:07 pm-1:48 am

1 stop9h 41m

Port of Spain Piarco Intl

Sun 10/26

4:01 am-1:42 pm

1 stop10h 41m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/10

3:50 pm-1:25 am

1 stop8h 35m

Port of Spain Piarco Intl

Sun 10/12

2:25 am-8:11 pm

2 stops18h 46m

$517

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 6/13

1:43 pm-6:55 pm

1 stop28h 12m

Port of Spain Piarco Intl

Fri 6/20

10:10 am-8:50 am

1 stop23h 40m

$531

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/29

9:21 am-11:23 pm

1 stop13h 02m

Port of Spain Piarco Intl

Wed 6/4

12:30 am-7:55 pm

1 stop20h 25m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 6/13

8:21 am-9:36 pm

1 stop12h 15m

Port of Spain Piarco Intl

Fri 6/20

7:09 am-10:29 pm

1 stop16h 20m

$539

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 6/13

1:43 pm-10:00 pm

2 stops31h 17m

Scarborough ANR Robinson Intl

Fri 6/20

7:35 am-8:50 am

2 stops26h 15m

$608

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 6/13

6:15 am-6:04 pm

1 stop10h 49m

Port of Spain Piarco Intl

Fri 6/20

7:29 pm-10:13 am

1 stop15h 44m

$698

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 5/7

9:55 am-1:47 am

2 stops14h 52m

$207

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/5

12:00 pm-1:25 am

1 stop12h 25m

$235

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 5/6

9:25 am-11:23 pm

1 stop12h 58m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April 30, 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 April 30, 2025.
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.7

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LIM - PTY

you go security buy an expensive bottle of water to take on the plane and then you have to go to another security point where they confiscate your water, the planes left on time and arrived on time. excellent food was mostly tasteless and overheated, no entertainment. wifi was glitchy.
Copa Airlines
7.5
Good
1,411 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.7

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LIM - PTY

you go security buy an expensive bottle of water to take on the plane and then you have to go to another security point where they confiscate your water, the planes left on time and arrived on time. excellent food was mostly tasteless and overheated, no entertainment. wifi was glitchy.
United Airlines
7.4
Good
8,696 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.7

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LIM - PTY

you go security buy an expensive bottle of water to take on the plane and then you have to go to another security point where they confiscate your water, the planes left on time and arrived on time. excellent food was mostly tasteless and overheated, no entertainment. wifi was glitchy.
JetBlue
7.3
Good
2,922 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.7

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LIM - PTY

you go security buy an expensive bottle of water to take on the plane and then you have to go to another security point where they confiscate your water, the planes left on time and arrived on time. excellent food was mostly tasteless and overheated, no entertainment. wifi was glitchy.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.7

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LIM - PTY

you go security buy an expensive bottle of water to take on the plane and then you have to go to another security point where they confiscate your water, the planes left on time and arrived on time. excellent food was mostly tasteless and overheated, no entertainment. wifi was glitchy.
Air Canada
7.0
Good
9,244 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.7

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LIM - PTY

you go security buy an expensive bottle of water to take on the plane and then you have to go to another security point where they confiscate your water, the planes left on time and arrived on time. excellent food was mostly tasteless and overheated, no entertainment. wifi was glitchy.

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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See prices for flight routes from nearby airports that may be better suited for you.
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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$618FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$614FlexibilityNo cancel feeOn-time71%

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