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Trinidad and Tobago

$688+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
jul. 30 — ago. 61
mié. 7/30
mié. 8/6
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 julio 25, 2025.

Round-trip from

$688
(American Airlines)

Popular in

January

Cheapest in

November

Average price

$838
From Chesapeake to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($187 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 July 2025
Search Deals

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 julio 25, 2025.

This American Airlines deal was found by Cheapflights users on 7/22. 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.
mar. 10/286:00 amORF - POS
1 stop8h 25mAmerican Airlines
vie. 10/317:00 amPOS - ORF
1 stop16h 16mAmerican Airlines
Deal found 7/22$688
This United Airlines deal was found by Cheapflights users on 7/23. 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.
mar. 10/286:07 amORF - POS
1 stop17h 16mUnited Airlines
jue. 10/3012:30 amPOS - ORF
2 stops14h 34mUnited Airlines
Deal found 7/23$703

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 julio 25, 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

mar. 10/28

6:00 am-2:25 pm

1 stop8h 25m

Port of Spain Piarco Intl

vie. 10/31

7:00 am-11:16 pm

1 stop16h 16m

$688

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mar. 10/28

6:07 am-11:23 pm

1 stop17h 16m

Port of Spain Piarco Intl

jue. 10/30

12:30 am-3:04 pm

2 stops14h 34m

$703

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

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

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.

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 julio 25, 2025.
Get a feel of what it's like to fly with United Airlines and 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.
United Airlines
7.4
Good
8,880 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,880 reviews
United Airlines
7.4
Good
8,880 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,880 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • 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 julio 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$513Average$752FlexibilityNo cancel feeOn-time71%

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