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Trinidad and Tobago

$246+ Cheap flights from Chesapeake, VA 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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Cheap 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 February 19, 2026.

This United Airlines deal was found by Cheapflights users on 2/18. 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 4/219:45 am
ORF
-
POS
2 stops13h 38m
United Airlines
Sun 5/1012:30 am
POS
-
ORF
2 stops20h 34m
United Airlines
Deal found 2/18$564
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 5/238:27 pm
ORF
-
POS
1 stop23h 33m
Multiple Airlines
Fri 5/2910:10 am
POS
-
ORF
1 stop9h 22m
Multiple Airlines
Deal found 2/18$570
This United Airlines deal was found by Cheapflights users on 2/18. 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 7/18:00 am
ORF
-
POS
2 stops15h 23m
United Airlines
Wed 7/2212:30 am
POS
-
ORF
2 stops14h 44m
United Airlines
Deal found 2/18$575
This United Airlines deal was found by Cheapflights users on 2/18. 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 5/98:00 am
ORF
-
POS
2 stops15h 23m
United Airlines
Sun 5/1012:30 am
POS
-
ORF
2 stops20h 34m
United Airlines
Deal found 2/18$584
This United Airlines deal was found by Cheapflights users on 2/15. 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 4/26:11 am
ORF
-
POS
2 stops17h 12m
United Airlines
Wed 4/812:30 am
POS
-
ORF
2 stops13h 50m
United Airlines
Deal found 2/15$589
This United Airlines deal was found by Cheapflights users on 2/18. 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 5/236:15 am
ORF
-
POS
1 stop17h 08m
United Airlines
Thu 5/2812:30 am
POS
-
ORF
2 stops13h 47m
United Airlines
Deal found 2/18$603
This American Airlines deal was found by Cheapflights users on 2/15. 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 4/156:15 am
ORF
-
POS
1 stop8h 17m
American Airlines
Sat 4/253:47 pm
POS
-
ORF
1 stop8h 12m
American Airlines
Deal found 2/15$610
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/97:52 pm
ORF
-
POS
1 stop18h 40m
American Airlines
Mon 5/113:47 pm
POS
-
ORF
1 stop8h 12m
American Airlines
Deal found 2/18$621

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 February 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$564
(United Airlines)

One-way from

$246
(Kiwi.com)
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
Search Deals
One-way flight from Chesapeake to Trinidad and Tobago
Search Deals

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 February 19, 2026.
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

Tue 4/21

9:45 am-11:23 pm

2 stops13h 38m

Port of Spain Piarco Intl

Sun 5/10

12:30 am-9:04 pm

2 stops20h 34m

$564

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 5/23

8:27 pm-8:00 pm

1 stop23h 33m

Port of Spain Piarco Intl

Fri 5/29

10:10 am-7:32 pm

1 stop9h 22m

$570

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Wed 7/1

8:00 am-11:23 pm

2 stops15h 23m

Port of Spain Piarco Intl

Wed 7/22

12:30 am-3:14 pm

2 stops14h 44m

$575

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 5/9

8:00 am-11:23 pm

2 stops15h 23m

Port of Spain Piarco Intl

Sun 5/10

12:30 am-9:04 pm

2 stops20h 34m

$584

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 4/2

6:11 am-11:23 pm

2 stops17h 12m

Port of Spain Piarco Intl

Wed 4/8

12:30 am-2:20 pm

2 stops13h 50m

$589

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 5/23

6:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

Thu 5/28

12:30 am-2:17 pm

2 stops13h 47m

$603

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Fri 4/17

6:15 am-2:32 pm

1 stop8h 17m

Port of Spain Piarco Intl

Sat 4/25

3:47 pm-11:59 pm

1 stop8h 12m

$610

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Tue 4/21

6:15 am-2:32 pm

1 stop8h 17m

Port of Spain Piarco Intl

Mon 5/11

3:47 pm-11:59 pm

1 stop8h 12m

$610

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Wed 3/25

8:41 pm-8:00 pm

1 stop23h 19m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

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 February 19, 2026.
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
11,313 reviews

Overall

7.2

Comfort

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,313 reviews
American Airlines
7.2
Good
11,313 reviews

Overall

7.2

Comfort

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 $564, United Airlines can have you in Trinidad and Tobago from Chesapeake in 13h 38m. 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 February 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$549Average$758FlexibilityNo cancel feeOn-time71%

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