Trinidad and Tobago

$253+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Jul 17 — Jul 241
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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 June 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 8/207:55 am
ORD
-
POS
1 stop11h 05m
Multiple Airlines
Sun 8/2310:10 am
POS
-
ORD
1 stop27h 15m
Multiple Airlines
Deal found 6/16$538
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Mon 7/138:05 am
ORD
-
POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
-
ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13$549
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Thu 7/98:05 am
ORD
-
POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
-
ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13$563
This JetBlue deal was found by Cheapflights users on 6/17. 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.
Tue 8/46:00 am
ORD
-
POS
1 stop11h 35m
JetBlue
Tue 8/117:41 pm
POS
-
ORD
1 stop14h 07m
JetBlue
Deal found 6/17$585
This Orbitz deal was found by Cheapflights users on 6/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/29:50 am
ORD
-
POS
1 stop13h 25m
Air Canada
Fri 8/71:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Deal found 6/15$593
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sun 7/128:05 am
ORD
-
POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
-
ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13$598
This Air Canada deal was found by Cheapflights users on 6/13. 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 7/138:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Sun 7/191:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 6/13$602
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Thu 7/23:45 pm
ORD
-
POS
1 stop31h 30m
Air Canada
Sun 7/51:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Deal found 6/15$603
This Air Canada deal was found by Cheapflights users on 6/13. 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 7/38:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Sun 7/191:25 am
POS
-
ORD
2 stops18h 19m
Air Canada
Deal found 6/13$610
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Tue 7/79:57 pm
ORD
-
POS
2 stops43h 58m
Multiple Airlines
Fri 7/1710:10 am
POS
-
ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13$611
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Fri 7/319:50 am
ORD
-
TAB
2 stops29h 45m
Multiple Airlines
Fri 8/73:30 pm
TAB
-
ORD
2 stops26h 27m
Multiple Airlines
Deal found 6/15$950
This Travelocity deal was found by Cheapflights users on 6/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/154:40 pm
ORD
-
TAB
2 stops19h 35m
Multiple Airlines
Sun 1/310:20 pm
TAB
-
ORD
3 stops36h 40m
Multiple Airlines
Deal found 6/14$4,053

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 June 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$538
(Kiwi.com)

One-way from

$253
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$669
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
From Chicago (CHI) to Trinidad and Tobago
One-way flight from Chicago (CHI) to Trinidad and Tobago
Highest demand for flights based on searches. 39% potential increase in price ($440 potential increase over avg. RT price).
Cheapest flight prices on average. 18% potential price decrease ($105 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 June 17, 2026.
Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/4

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Tue 8/11

7:41 pm-8:48 am

1 stop14h 07m

$585

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 7/17

3:21 pm-1:46 am

1 stop9h 25m

Port of Spain Piarco Intl

Sun 7/19

2:19 pm-1:57 pm

1 stop24h 38m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 7/11

8:02 am-1:46 am

1 stop16h 44m

Port of Spain Piarco Intl

Sat 7/18

2:19 pm-12:01 am

1 stop10h 42m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 7/21

1:20 am-1:16 pm

1 stop10h 56m

Port of Spain Piarco Intl

Sun 7/26

2:19 pm-1:57 pm

1 stop24h 38m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 7/17

3:21 pm-1:46 am

1 stop9h 25m

Port of Spain Piarco Intl

Fri 7/24

2:19 pm-4:00 am

1 stop14h 41m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 7/18

8:02 am-1:46 am

1 stop16h 44m

Port of Spain Piarco Intl

Sun 8/9

2:19 pm-1:02 am

1 stop11h 43m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 8/12

8:02 am-1:17 pm

1 stop28h 15m

Port of Spain Piarco Intl

Sun 8/16

2:19 pm-1:02 am

1 stop11h 43m

$618

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 7/14

8:02 am-1:46 am

1 stop16h 44m

Port of Spain Piarco Intl

Mon 7/20

3:50 am-12:01 am

1 stop21h 11m

$618
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 7/18

10:51 am-12:50 am

1 stop12h 59m

Port of Spain Piarco Intl

Thu 7/23

12:30 am-10:20 am

1 stop10h 50m

$630

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 7/14

5:00 am-10:33 pm

1 stop16h 33m

Port of Spain Piarco Intl

Tue 7/21

7:00 am-10:00 pm

2 stops16h 00m

$634

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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, January is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $285). Flying from Chicago to Trinidad and Tobago in September is currently the most expensive (average of $562). 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 June 17, 2026.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as American Airlines and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

6.8

Crew

7.9

Overall

7.1

Boarding

7.5

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

Entertainment

6.8

Crew

7.9

Overall

7.1

Boarding

7.5

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

Entertainment

6.8

Crew

7.9

Overall

7.1

Boarding

7.5

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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 9h 25m. The distance between Chicago and Trinidad and Tobago is about 2697 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $285). Flying from Chicago to Trinidad and Tobago in September is currently the most expensive (average of $562). 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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Top 4 airlines flying from Chicago to Trinidad and Tobago

Discover the top 4 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 June 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$285Average$627FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$317Average$515FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$548Average$669FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$649FlexibilityNo cancel feeOn-time69%

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