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Trinidad and Tobago

$486+ Cheap flights from Chicago (CHI) to Trinidad and Tobago

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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Cheap flight deals from Chicago to Trinidad and Tobago

Keep the following information in mind while searching for Chicago to Trinidad and Tobago flight deals. Data was last updated April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$486
(Copa Airlines)

Popular in

February

Cheapest in

January

Average price

$674
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 and Tobago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($153 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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Find flight deals from Chicago to Trinidad and Tobago

Cheapest flights from Chicago to Trinidad and Tobago
Explore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 4, 2025.

This Copa Airlines deal was found by Cheapflights users on 4/4. 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 5/193:07 pmORD - POS
1 stop9h 40mCopa Airlines
Sun 5/253:44 amPOS - ORD
1 stop11h 03mCopa Airlines
Deal found 4/4$486
This Air Canada deal was found by Cheapflights users on 4/4. 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 5/1912:00 pmORD - POS
1 stop12h 25mAir Canada
Sun 5/252:25 amPOS - ORD
2 stops18h 47mAir Canada
Deal found 4/4$516
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Sat 5/109:08 pmORD - POS
1 stop14h 22mMultiple Airlines
Sun 5/113:44 amPOS - ORD
2 stops38h 57mMultiple Airlines
Deal found 4/3$520
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Sat 5/105:15 amORD - POS
1 stop17h 08mUnited Airlines
Sun 5/1112:30 amPOS - ORD
1 stop10h 41mUnited Airlines
Deal found 4/3$538
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Sat 5/108:45 pmORD - POS
2 stops16h 20mAmerican Airlines
Mon 5/123:05 pmPOS - ORD
1 stop18h 55mAmerican Airlines
Deal found 4/3$543
This Mytrip deal was found by Cheapflights users on 4/3. 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 5/182:00 pmORD - TAB
2 stops15h 10mMultiple Airlines
Sun 5/259:15 amTAB - ORD
2 stops26h 39mMultiple Airlines
Deal found 4/3$654

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 4, 2025.
Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

Fly from

Chicago

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/19

3:07 pm-1:47 am

1 stop9h 40m

Port of Spain Piarco Intl

Sun 5/25

3:44 am-1:47 pm

1 stop11h 03m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/19

12:00 pm-1:25 am

1 stop12h 25m

Port of Spain Piarco Intl

Sun 5/25

2:25 am-8:12 pm

2 stops18h 47m

$516

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/10

9:08 pm-12:30 pm

1 stop14h 22m

Port of Spain Piarco Intl

Sun 5/11

3:44 am-5:41 pm

2 stops38h 57m

$520

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/10

5:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

Sun 5/11

12:30 am-10:11 am

1 stop10h 41m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/10

8:45 pm-2:05 pm

2 stops16h 20m

Port of Spain Piarco Intl

Mon 5/12

3:05 pm-9:00 am

1 stop18h 55m

$543

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sun 5/18

2:00 pm-6:10 am

2 stops15h 10m

Scarborough ANR Robinson Intl

Sun 5/25

9:15 am-10:54 am

2 stops26h 39m

$654

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Best time to book a flight from Chicago to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago 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 and Tobago

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

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

Find hourly flight availability from Chicago 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 4, 2025.

When flying from Chicago to Trinidad and Tobago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 4, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines and American Airlines from Chicago to Trinidad and Tobago by reading reviews from past customers. 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
1,404 reviews

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.6

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
1,404 reviews
Copa Airlines
7.6
Good
1,404 reviews

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.6

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
8,618 reviews
Copa Airlines
7.6
Good
1,404 reviews

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.6

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
1,404 reviews

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.6

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
9,035 reviews
Copa Airlines
7.6
Good
1,404 reviews

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.6

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 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 Chicago to Trinidad and Tobago that include hotel bookings?

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

  • How can I find direct flights from Chicago 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 Chicago to Trinidad and Tobago.

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

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

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

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 Chicago to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Trinidad and Tobago

Discover the top 2 airlines that operate flights from Chicago 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$618FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$607FlexibilityNo cancel feeOn-time71%

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