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Trinidad

$292+ Cheap flights from Chicago (CHI) to Trinidad

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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Cheap flight deals from Chicago to Trinidad

Keep the following information in mind while searching for Chicago to Trinidad flight deals. Data was last updated April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$485
(Mytrip)

One-way from

$292
(Mytrip)

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 Chicago (CHI) to Trinidad
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One-way flight from Chicago (CHI) to Trinidad
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Highest demand for flights based on searches. 17% potential increase in price ($152 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($61 potential savings vs. average RT price).
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Find flight deals from Chicago to Trinidad

Cheapest flights from Chicago to Trinidad
Explore the most affordable flight options available from Chicago to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

This Mytrip deal was found by Cheapflights users on 4/15. 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.
Sun 5/45:55 amORD - POS
2 stops13h 05mMultiple Airlines
Tue 5/139:10 amPOS - ORD
1 stop9h 31mMultiple Airlines
Deal found 4/15$485
This Copa Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 5/53:07 pmORD - POS
1 stop9h 40mCopa Airlines
Tue 5/133:44 amPOS - ORD
1 stop11h 03mCopa Airlines
Deal found 4/14$492
This Air Canada deal was found by Cheapflights users on 4/14. 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 5/33:35 pmORD - POS
2 stops32h 50mAir Canada
Mon 5/52:25 amPOS - ORD
2 stops30h 08mAir Canada
Deal found 4/14$512
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 5/57:16 pmORD - POS
1 stop17h 49mAmerican Airlines
Fri 5/93:05 pmPOS - ORD
1 stop18h 55mAmerican Airlines
Deal found 4/14$538
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Mon 5/55:15 amORD - POS
1 stop17h 08mUnited Airlines
Wed 5/1412:30 amPOS - ORD
1 stop12h 01mUnited Airlines
Deal found 4/15$539

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Trinidad 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 15, 2025.
Use the filters below to find and compare flights from Chicago to Trinidad that are best for you.

Fly from

Chicago

Fly to

Trinidad

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 5/4

5:55 am-8:00 pm

2 stops13h 05m

Port of Spain Piarco Intl

Tue 5/13

9:10 am-5:41 pm

1 stop9h 31m

$485

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/5

3:07 pm-1:47 am

1 stop9h 40m

Port of Spain Piarco Intl

Tue 5/13

3:44 am-1:47 pm

1 stop11h 03m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/3

3:35 pm-1:25 am

2 stops32h 50m

Port of Spain Piarco Intl

Mon 5/5

2:25 am-7:33 am

2 stops30h 08m

$512

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/5

7:16 pm-2:05 pm

1 stop17h 49m

Port of Spain Piarco Intl

Fri 5/9

3:05 pm-9:00 am

1 stop18h 55m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/5

5:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

Wed 5/14

12:30 am-11:31 am

1 stop12h 01m

$539

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 4/26

9:09 am-6:10 pm

2 stops32h 01m

$292

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 4/26

9:15 am-11:23 pm

1 stop13h 08m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Best time to book a flight from Chicago to Trinidad

Have a flexible travel schedule? Discover the best time to fly to Trinidad from Chicago 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 Chicago to Trinidad

What is the cheapest month to book a flight from Chicago to Trinidad?

Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad 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 CHI to LAZ?

Find hourly flight availability from Chicago to Trinidad. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 15, 2025.

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

Rainfall in Trinidad by month

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

In terms of precipitation, rainfall in Trinidad 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 when rainfall is around 1.2 in.

Temperature in Trinidad by month

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

If weather is an important factor for your trip to Trinidad, 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

Get insights into the airlines that provide service to Trinidad. 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. Reviews last updated April 15, 2025.
Copa Airlines
7.6
Good
1,408 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Boarding

7.8

Overall

7.6

Entertainment

6.8

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
7.6
Good
1,408 reviews
Copa Airlines
7.6
Good
1,408 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Boarding

7.8

Overall

7.6

Entertainment

6.8

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
8,658 reviews
Copa Airlines
7.6
Good
1,408 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Boarding

7.8

Overall

7.6

Entertainment

6.8

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
7.6
Good
1,408 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Boarding

7.8

Overall

7.6

Entertainment

6.8

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
9,127 reviews
Copa Airlines
7.6
Good
1,408 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Boarding

7.8

Overall

7.6

Entertainment

6.8

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 Chicago to Trinidad. 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 Chicago to Trinidad that include hotel bookings?

    Yes. In addition to deals on Chicago to Trinidad flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Trinidad?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Trinidad.

  • Can I find deals for business class flights from Chicago to Trinidad?

    Yes. Cheapflights offers flight deals from Chicago to Trinidad 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 Chicago to Trinidad?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Trinidad

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Port of Spain flights
St. Louis to Port of Spain flights
O'Hare Intl to Scarborough flights

Top 2 airlines flying from Chicago to Trinidad

Discover the top 2 airlines that operate flights from Chicago to Trinidad. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$618FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$612FlexibilityNo cancel feeOn-time71%

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