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Trinidad and Tobago

$251+ Cheap flights from O'Hare Intl (ORD) 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Trinidad and Tobago

Cheapest flights from O'Hare Intl to Trinidad and Tobago
Explore the most affordable flight options available from O'Hare Intl to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Copa Airlines deal was found by Cheapflights users on 12/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:33 amORD - POS
1 stop16h 15mCopa Airlines
Wed 12/243:13 amPOS - ORD
1 stop11h 39mCopa Airlines
Deal found 12/17$567
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:41 pmORD - POS
2 stops32h 37mJetBlue
Wed 1/78:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 12/16$759
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Thu 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$765
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Fri 1/99:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$777
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:38 pmORD - POS
2 stops19h 17mMultiple Airlines
Tue 12/232:15 amPOS - ORD
1 stop14h 55mMultiple Airlines
Deal found 12/16$804
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Wed 1/79:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 12/16$846
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/175:40 amORD - POS
2 stops12h 40mMultiple Airlines
Thu 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$867
This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:30 pmORD - TAB
2 stops20h 00mMultiple Airlines
Fri 12/2610:20 pmTAB - ORD
2 stops23h 25mMultiple Airlines
Deal found 12/17$1,314

Find flight deals from O'Hare Intl to Trinidad and Tobago

Keep the following information in mind while searching for O'Hare Intl to Trinidad and Tobago flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$391
(Trip.com)

One-way from

$251
(Expedia)

Popular in

December

Cheapest in

October

Average price

$1,705
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 O'Hare Intl to Trinidad and Tobago
Search Deals
One-way flight from Chicago O'Hare Intl to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($425 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($107 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Trinidad and Tobago that are best for you.

Fly from

O'Hare Intl

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/15

5:15 am-8:00 pm

1 stop12h 45m

Port of Spain Piarco Intl

Thu 1/22

10:10 am-9:03 pm

1 stop12h 53m

$391

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

7:20 am-8:00 pm

1 stop10h 40m

Port of Spain Piarco Intl

Fri 2/6

10:10 am-7:38 pm

1 stop11h 28m

$435

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Thu 2/5

2:20 am-6:55 pm

2 stops18h 35m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/31

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 2/6

2:20 am-1:01 pm

1 stop12h 41m

$453

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

6:04 pm-12:20 am

2 stops29h 16m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:20 pm-12:20 am

2 stops29h 00m

Port of Spain Piarco Intl

Mon 4/6

3:40 pm-9:10 am

2 stops18h 30m

$480

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sat 1/31

8:45 pm-7:05 pm

2 stops20h 20m

Scarborough ANR Robinson Intl

Sat 2/7

10:20 pm-6:16 pm

2 stops21h 56m

$855

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Thu 2/12

8:40 pm-6:50 am

3 stops32h 10m

Scarborough ANR Robinson Intl

Thu 2/19

10:20 pm-11:47 pm

3 stops27h 27m

$1,293

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/24

7:41 pm-2:31 pm

2 stops16h 50m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 12 results
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Best time to book a flight from O'Hare Intl to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from O'Hare Intl 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 O'Hare Intl Airport to Trinidad and Tobago

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago?

Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago (average of $435). Flying from Chicago O'Hare Intl Airport 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.

What is the cheapest time of day to fly from ORD to TT?

Find hourly flight availability from O'Hare Intl 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 December 18, 2025.

When flying from Chicago O'Hare Intl Airport to Trinidad and Tobago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 41% versus a flight in the evening.

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 December 18, 2025.
See what other customers who have flown with United Airlines, American Airlines, and Air Canada from Chicago O'Hare Intl Airport to Trinidad and Tobago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,093 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
United Airlines
7.4
Good
9,093 reviews
United Airlines
7.4
Good
9,093 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
American Airlines
7.2
Good
11,055 reviews
United Airlines
7.4
Good
9,093 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
Air Canada
7.1
Good
10,534 reviews
United Airlines
7.4
Good
9,093 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl 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 O'Hare Intl Airport to Trinidad and Tobago?

    Air Canada can get you from Chicago O'Hare Intl Airport to Trinidad and Tobago in just under 9h 20m. Your travel time can differ by up to . The distance between Chicago O'Hare Intl Airport and Trinidad and Tobago is about 2697 mi.

  • Can I find deals for flights from O'Hare Intl to Trinidad and Tobago that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl 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 O'Hare Intl to Trinidad and Tobago.

  • Can I find deals for business class flights from O'Hare Intl to Trinidad and Tobago?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Trinidad and Tobago?

    Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago (average of $435). Flying from Chicago O'Hare Intl Airport 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 O'Hare Intl 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 O'Hare Intl to Trinidad and Tobago

Discover the top 3 airlines that operate flights from O'Hare Intl 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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