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Trinidad and Tobago

$553+ Cheap flights from Chesapeake, VA 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap flight deals from Chesapeake to Trinidad and Tobago

Best flights from Chesapeake to Trinidad and Tobago
Discover carefully curated flight deals from Chesapeake to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 26, 2025.

This United Airlines deal was found by Cheapflights users on 12/25. 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 1/246:00 amORF - POS
1 stop17h 23mUnited Airlines
Fri 1/301:30 amPOS - ORF
2 stops16h 36mUnited Airlines
Deal found 12/25$553
This American Airlines deal was found by Cheapflights users on 12/25. 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 4/47:05 pmORF - POS
2 stops19h 13mAmerican Airlines
Fri 4/103:10 pmPOS - ORF
2 stops19h 56mAmerican Airlines
Deal found 12/25$813
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 4/48:29 pmORF - POS
1 stop23h 31mMultiple Airlines
Fri 4/1010:10 amPOS - ORF
1 stop9h 21mMultiple Airlines
Deal found 12/25$918
This United Airlines deal was found by Cheapflights users on 12/25. 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.
Thu 2/196:00 amORF - POS
1 stop17h 23mUnited Airlines
Sun 2/221:30 amPOS - ORF
2 stops33h 18mUnited Airlines
Deal found 12/25$701
This American Airlines deal was found by Cheapflights users on 12/24. 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.
Thu 2/197:42 pmORF - POS
1 stop16h 36mAmerican Airlines
Mon 2/234:40 pmPOS - ORF
1 stop27h 32mAmerican Airlines
Deal found 12/24$928
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 2/127:13 pmORF - POS
1 stop23h 17mMultiple Airlines
Tue 2/173:13 amPOS - ORF
2 stops19h 37mMultiple Airlines
Deal found 12/24$1,063

Find flight deals from Chesapeake to Trinidad and Tobago

Keep the following information in mind while searching for Chesapeake to Trinidad and Tobago flight deals. Data was last updated December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$553
(United Airlines)
Provider with most accurate pricing for Norfolk-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Port of Spain Piarco Intl flights.
Search Deals
From Chesapeake to Trinidad and Tobago
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake 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 26, 2025.
Use the filters below to find and compare flights from Chesapeake to Trinidad and Tobago that are best for you.

Fly from

Chesapeake

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 1/24

6:00 am-12:23 am

1 stop17h 23m

Port of Spain Piarco Intl

Fri 1/30

1:30 am-5:06 pm

2 stops16h 36m

$553

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 2/19

6:00 am-12:23 am

1 stop17h 23m

Port of Spain Piarco Intl

Sun 2/22

1:30 am-9:48 am

2 stops33h 18m

$701

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 4/4

7:05 pm-2:18 pm

2 stops19h 13m

Port of Spain Piarco Intl

Fri 4/10

3:10 pm-11:06 am

2 stops19h 56m

$813

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 4/4

8:29 pm-8:00 pm

1 stop23h 31m

Port of Spain Piarco Intl

Fri 4/10

10:10 am-7:31 pm

1 stop9h 21m

$918

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 2/19

7:42 pm-1:18 pm

1 stop16h 36m

Port of Spain Piarco Intl

Mon 2/23

4:40 pm-7:12 pm

1 stop27h 32m

$928

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 2/12

7:13 pm-7:30 pm

1 stop23h 17m

Port of Spain Piarco Intl

Tue 2/17

3:13 am-9:50 pm

2 stops19h 37m

$1,063

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from Chesapeake 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 Chesapeake to Trinidad and Tobago
No data available for this route at this time. Please check back soon.

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 26, 2025.
Get a feel of what it's like to fly with American Airlines from Chesapeake to Trinidad and Tobago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,067 reviews

Entertainment

6.9

Comfort

7.2

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,067 reviews
American Airlines
7.2
Good
11,067 reviews

Entertainment

6.9

Comfort

7.2

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

Find useful and relevant information for your journey from Chesapeake 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 Chesapeake to Trinidad and Tobago?

    For as low as $553, United Airlines can have you in Trinidad and Tobago from Chesapeake in 17h 23m. Airlines will cover a distance of 2038 mi.

  • Can I find deals for flights from Chesapeake to Trinidad and Tobago that include hotel bookings?

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

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

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

    Yes. Cheapflights offers flight deals from Chesapeake 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.

See more FAQs

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Alternative routes for Chesapeake to Trinidad and Tobago

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

Discover the top airline that operate flights from Chesapeake 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 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$513Average$753FlexibilityNo cancel feeOn-time71%

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