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Trinidad and Tobago

$513+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$513
(United Airlines)

Popular in

January

Cheapest in

November

Average price

$866
From Chesapeake to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($197 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Chesapeake to Trinidad and Tobago

Cheapest flights from Chesapeake to Trinidad and Tobago
Explore the most affordable flight options available from Chesapeake to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/87:59 pmORF - POS
2 stops27h 24mUnited Airlines
Tue 10/1412:30 amPOS - ORF
2 stops18h 00mUnited Airlines
Deal found 9/10$513
This Expedia deal was found by Cheapflights users on 9/10. 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 10/810:25 amORF - POS
2 stops28h 09mJetBlue
Wed 10/153:59 pmPOS - ORF
2 stops17h 40mJetBlue
Deal found 9/10$630
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/86:00 amORF - POS
1 stop8h 25mAmerican Airlines
Wed 10/157:00 amPOS - ORF
1 stop16h 16mAmerican Airlines
Deal found 9/10$658
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 10/286:35 amORF - POS
2 stops16h 48mUnited Airlines
Thu 10/3012:30 amPOS - ORF
2 stops21h 08mUnited Airlines
Deal found 9/10$718
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/286:00 amORF - POS
1 stop15h 20mAmerican Airlines
Fri 10/317:00 amPOS - ORF
1 stop16h 16mAmerican Airlines
Deal found 9/9$728
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Wed 10/16:15 amORF - POS
1 stop8h 01mAmerican Airlines
Wed 10/87:00 amPOS - ORF
1 stop16h 16mAmerican Airlines
Deal found 9/11$738
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Wed 10/16:15 amORF - POS
1 stop17h 08mUnited Airlines
Tue 10/712:30 amPOS - ORF
2 stops14h 10mUnited Airlines
Deal found 9/11$758

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 September 11, 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

Wed 10/8

6:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

Tue 10/14

12:30 am-6:30 pm

2 stops18h 00m

$513

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Tue 10/28

6:00 am-11:23 pm

2 stops17h 23m

Port of Spain Piarco Intl

Thu 10/30

12:30 am-9:38 pm

2 stops21h 08m

$718

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Tue 10/28

6:00 am-9:20 pm

1 stop15h 20m

Port of Spain Piarco Intl

Fri 10/31

7:00 am-11:16 pm

1 stop16h 16m

$728

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Wed 10/1

6:15 am-2:16 pm

1 stop8h 01m

Port of Spain Piarco Intl

Wed 10/8

7:00 am-11:16 pm

1 stop16h 16m

$738

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 September 11, 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
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 $513, United Airlines can have you in Trinidad and Tobago from Chesapeake in 17h 08m. 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.

  • What is the cheapest month to book a flight from Chesapeake to Trinidad and Tobago?

    Currently, October is the cheapest month in which you can book a flight from Chesapeake to Trinidad and Tobago (average of $435). Flying from Chesapeake to Trinidad and Tobago 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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$513Average$752FlexibilityNo cancel feeOn-time71%

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