HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad

$207+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Trinidad with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 abril 29, 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.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
Search Deals
From Chicago (CHI) to Trinidad
Search Deals
One-way flight from Chicago (CHI) to Trinidad
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).
Search Deals

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 abril 29, 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.
mié. 10/223:07 pmORD - POS
1 stop9h 41mCopa Airlines
dom. 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.
vie. 10/103:50 pmORD - POS
1 stop8h 35mAir Canada
dom. 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.
vie. 6/131:43 pmORD - POS
1 stop28h 12mMultiple Airlines
vie. 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.
jue. 5/299:21 amORD - POS
1 stop13h 02mUnited Airlines
mié. 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.
vie. 6/138:21 amORD - POS
1 stop12h 15mAmerican Airlines
vie. 6/207:09 amPOS - ORD
1 stop16h 20mAmerican Airlines
Deal found 4/29$539
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.
vie. 6/136:15 amORD - POS
1 stop10h 49mJetBlue
vie. 6/207:29 pmPOS - ORD
1 stop15h 44mJetBlue
Deal found 4/29$698

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 abril 29, 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

mié. 10/22

3:07 pm-1:48 am

1 stop9h 41m

Port of Spain Piarco Intl

dom. 10/26

4:01 am-1:42 pm

1 stop10h 41m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 10/10

3:50 pm-1:25 am

1 stop8h 35m

Port of Spain Piarco Intl

dom. 10/12

2:25 am-8:11 pm

2 stops18h 46m

$517

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 6/13

1:43 pm-6:55 pm

1 stop28h 12m

Port of Spain Piarco Intl

vie. 6/20

10:10 am-8:50 am

1 stop23h 40m

$531

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 5/29

9:21 am-11:23 pm

1 stop13h 02m

Port of Spain Piarco Intl

mié. 6/4

12:30 am-7:55 pm

1 stop20h 25m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 6/13

8:21 am-9:36 pm

1 stop12h 15m

Port of Spain Piarco Intl

vie. 6/20

7:09 am-10:29 pm

1 stop16h 20m

$539

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 6/13

6:15 am-6:04 pm

1 stop10h 49m

Port of Spain Piarco Intl

vie. 6/20

7:29 pm-10:13 am

1 stop15h 44m

$698

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 5/7

9:55 am-1:47 am

2 stops14h 52m

$207

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 5/5

12:00 pm-1:25 am

1 stop12h 25m

$235

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 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 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 abril 29, 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 abril 29, 2025.
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Crew

8.1

Entertainment

6.7

Overall

7.5

Boarding

7.8

Food

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
7.5
Good
1,411 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Crew

8.1

Entertainment

6.7

Overall

7.5

Boarding

7.8

Food

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
8,696 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Crew

8.1

Entertainment

6.7

Overall

7.5

Boarding

7.8

Food

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.
JetBlue
7.3
Good
2,922 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Crew

8.1

Entertainment

6.7

Overall

7.5

Boarding

7.8

Food

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
7.5
Good
1,411 reviews

Comfort

7.4

Crew

8.1

Entertainment

6.7

Overall

7.5

Boarding

7.8

Food

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
9,244 reviews
Copa Airlines
7.5
Good
1,411 reviews

Comfort

7.4

Crew

8.1

Entertainment

6.7

Overall

7.5

Boarding

7.8

Food

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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
O'Hare Intl to Scarborough flights
St. Louis to Port of Spain 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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$618FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$614FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.