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Trinidad and Tobago

$205+ Cheap flights from Chicago (CHI) 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Air Canada deal was found by Cheapflights users on 1/28. 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 2/272:00 pm
ORD
-
POS
1 stop9h 20m
Air Canada
Thu 3/52:20 am
POS
-
ORD
1 stop14h 50m
Air Canada
Deal found 1/28$358
This Trip.com deal was found by Cheapflights users on 1/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/85:15 am
ORD
-
POS
1 stop13h 45m
Multiple Airlines
Mon 3/1610:10 am
POS
-
ORD
1 stop10h 36m
Multiple Airlines
Deal found 1/26$437
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:00 am
ORD
-
POS
2 stops19h 17m
Multiple Airlines
Thu 3/121:20 am
POS
-
ORD
1 stop19h 25m
Multiple Airlines
Deal found 1/27$446
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Wed 3/48:40 pm
ORD
-
POS
1 stop26h 40m
Air Canada
Tue 3/101:20 am
POS
-
ORD
1 stop14h 50m
Air Canada
Deal found 1/27$458
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Wed 5/68:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Sun 5/101:25 am
POS
-
ORD
1 stop13h 00m
Air Canada
Deal found 1/27$461
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/288:16 pm
ORD
-
POS
1 stop21h 44m
Multiple Airlines
Mon 3/29:10 am
POS
-
ORD
1 stop26h 29m
Multiple Airlines
Deal found 1/27$480
This Mytrip deal was found by Cheapflights users on 1/27. 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 2/228:42 pm
ORD
-
TAB
3 stops36h 18m
Multiple Airlines
Sun 3/19:00 pm
TAB
-
ORD
2 stops24h 45m
Multiple Airlines
Deal found 1/27$683
This Mytrip deal was found by Cheapflights users on 1/27. 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.
Sat 1/318:00 am
ORD
-
TAB
3 stops33h 35m
Multiple Airlines
Mon 2/27:35 am
TAB
-
ORD
2 stops18h 12m
Multiple Airlines
Deal found 1/27$860

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Air Canada)

One-way from

$205
(Air Canada)

Popular in

December

Cheapest in

October
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 and Tobago
Search Deals
One-way flight from Chicago (CHI) to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($449 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 17% potential price decrease ($116 potential savings vs. average RT price).
Search Deals

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 January 29, 2026.
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

Sun 3/29

6:21 pm-12:20 am

2 stops52h 59m

Port of Spain Piarco Intl

Tue 4/7

1:20 am-12:17 pm

2 stops35h 57m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/27

6:04 pm-1:20 am

2 stops53h 16m

Port of Spain Piarco Intl

Thu 3/5

2:20 am-6:52 pm

2 stops42h 32m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/8

5:15 am-8:00 pm

1 stop13h 45m

Port of Spain Piarco Intl

Mon 3/16

10:10 am-7:46 pm

1 stop10h 36m

$437

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 5/6

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Sun 5/10

1:25 am-1:25 pm

1 stop13h 00m

$458

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 3/4

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Tue 3/10

1:20 am-6:52 pm

2 stops18h 32m

$463

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 2/26

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Sun 3/1

2:20 am-7:45 pm

1 stop19h 25m

$468

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 2/28

4:42 pm-1:05 pm

2 stops18h 23m

Port of Spain Piarco Intl

Mon 3/2

9:10 am-9:39 am

1 stop26h 29m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

6:04 pm-12:20 am

2 stops53h 16m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$498

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sun 2/22

8:42 pm-11:00 am

3 stops36h 18m

Scarborough ANR Robinson Intl

Sun 3/1

9:00 pm-7:45 pm

2 stops24h 45m

$683

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 12 results
1
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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, November 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 April is currently the most expensive (average of $628). 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.

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 January 29, 2026.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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.

  • How long is the flight from Chicago to Trinidad and Tobago?

    Departing from Chicago to Trinidad and Tobago will take you 52h 59m. The distance between Chicago and Trinidad and Tobago is about 2697 mi.

  • 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, November 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 April is currently the most expensive (average of $628). 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 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 3 airlines flying from Chicago to Trinidad and Tobago

Discover the top 3 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$501Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$528Average$641FlexibilityNo cancel feeOn-time71%

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