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Trinidad and Tobago

$623+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
déc. 12 — déc. 191
ven. 12/12
ven. 12/19
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 novembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$623
(United Airlines)
Provider with most accurate pricing for Norfolk-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Port of Spain Piarco Intl flights.
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From Chesapeake to Trinidad and Tobago
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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 novembre 12, 2025.

This United Airlines deal was found by Cheapflights users on 11/10. 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.
lun. 12/16:35 amORF - POS
2 stops16h 48mUnited Airlines
sam. 12/131:30 amPOS - ORF
2 stops14h 04mUnited Airlines
Deal found 11/10$623
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/19:26 pmORF - POS
3 stops26h 44mMultiple Airlines
dim. 12/1410:10 amPOS - ORF
1 stop10h 06mMultiple Airlines
Deal found 11/10$669
This American Airlines deal was found by Cheapflights users on 11/10. 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.
lun. 12/16:00 amORF - POS
1 stop8h 30mAmerican Airlines
dim. 12/147:10 amPOS - ORF
1 stop12h 49mAmerican Airlines
Deal found 11/10$704
This United Airlines deal was found by Cheapflights users on 11/10. 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.
lun. 11/176:20 amORF - POS
2 stops17h 03mUnited Airlines
dim. 11/231:30 amPOS - ORF
2 stops13h 28mUnited Airlines
Deal found 11/10$738
This American Airlines deal was found by Cheapflights users on 11/10. 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.
lun. 11/176:00 amORF - POS
1 stop8h 30mAmerican Airlines
lun. 11/244:30 pmPOS - ORF
1 stop8h 45mAmerican Airlines
Deal found 11/10$789
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/177:00 amORF - POS
2 stops12h 00mMultiple Airlines
lun. 11/248:30 amPOS - ORF
1 stop13h 01mMultiple Airlines
Deal found 11/10$790
This United Airlines deal was found by Cheapflights users on 11/11. 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.
mer. 12/241:05 pmORF - POS
2 stops34h 18mUnited Airlines
mar. 12/302:20 amPOS - ORF
3 stops22h 21mUnited Airlines
Deal found 11/11$840

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 novembre 12, 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

lun. 12/1

6:35 am-12:23 am

2 stops16h 48m

Port of Spain Piarco Intl

sam. 12/13

1:30 am-2:34 pm

2 stops14h 04m

$623

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

lun. 12/1

9:26 pm-1:10 am

3 stops26h 44m

Port of Spain Piarco Intl

dim. 12/14

10:10 am-7:16 pm

1 stop10h 06m

$669

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

lun. 12/1

6:00 am-3:30 pm

1 stop8h 30m

Port of Spain Piarco Intl

dim. 12/14

7:10 am-6:59 pm

1 stop12h 49m

$704

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mer. 12/24

1:05 pm-12:23 am

2 stops34h 18m

Port of Spain Piarco Intl

mar. 12/30

2:20 am-10:59 am

1 stop9h 39m

$840

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

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 novembre 12, 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
11,049 reviews

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,049 reviews
American Airlines
7.2
Good
11,049 reviews

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 $704, United Airlines can have you in Trinidad and Tobago from Chesapeake in 8h 30m. Airlines will cover a distance of 2038 mi. This flight may include one or multiple stops.

  • 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 novembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$513Average$753FlexibilityNo cancel feeOn-time71%

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