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Port of Spain

$474+ Cheap flights from Chesapeake, VA to Port of Spain (POS)

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
nov. 6 — nov. 131
jue. 11/6
jue. 11/13
1 adult, Economy
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Find flight deals from Chesapeake to Port of Spain

Cheapest flights from Chesapeake to Port of Spain
Explore the most affordable flight options available from Chesapeake to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 7, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
jue. 11/67:53 pmORF - POS
1 stop23h 07mMultiple Airlines
jue. 11/1310:10 amPOS - ORF
1 stop9h 48mMultiple Airlines
Deal found 10/7$474
This United Airlines deal was found by Cheapflights users on 10/7. 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.
jue. 11/66:20 amORF - POS
2 stops17h 03mUnited Airlines
mié. 11/121:30 amPOS - ORF
2 stops16h 06mUnited Airlines
Deal found 10/7$513
This United Airlines deal was found by Cheapflights users on 10/7. 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.
mié. 10/226:15 amORF - POS
1 stop17h 08mUnited Airlines
mar. 11/41:30 amPOS - ORF
2 stops21h 08mUnited Airlines
Deal found 10/7$603
This United Airlines deal was found by Cheapflights users on 10/7. 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. 10/216:30 amORF - POS
2 stops16h 53mUnited Airlines
lun. 10/2712:30 amPOS - ORF
2 stops14h 04mUnited Airlines
Deal found 10/7$648
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
mié. 10/227:00 amORF - POS
2 stops37h 00mMultiple Airlines
mié. 11/58:30 amPOS - ORF
1 stop28h 51mMultiple Airlines
Deal found 10/7$655
This American Airlines deal was found by Cheapflights users on 10/7. 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.
mié. 10/226:00 amORF - POS
1 stop8h 25mAmerican Airlines
mié. 11/54:30 pmPOS - ORF
1 stop8h 45mAmerican Airlines
Deal found 10/7$699
This American Airlines deal was found by Cheapflights users on 10/7. 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. 10/216:00 amORF - POS
1 stop8h 25mAmerican Airlines
mar. 10/287:00 amPOS - ORF
1 stop16h 16mAmerican Airlines
Deal found 10/7$739

Cheap flight deals from Chesapeake to Port of Spain

Keep the following information in mind while searching for Chesapeake to Port of Spain flight deals. Data was last updated octubre 7, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$648
(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 Port of Spain Piarco Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Port of Spain 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 octubre 7, 2025.
Use the filters below to find and compare flights from Chesapeake to Port of Spain that are best for you.

Fly from

Chesapeake

Fly to

Port of Spain

Route

Depart

Return

Price

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

jue. 11/6

7:53 pm-8:00 pm

1 stop23h 07m

Port of Spain Piarco Intl

jue. 11/13

10:10 am-6:58 pm

1 stop9h 48m

$474

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mié. 10/22

6:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

mar. 11/4

1:30 am-9:38 pm

2 stops21h 08m

$603

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mar. 10/21

6:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

lun. 10/27

12:30 am-1:58 pm

2 stops13h 28m

$648

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mié. 10/22

7:00 am-8:00 pm

2 stops37h 00m

Port of Spain Piarco Intl

mié. 11/5

8:30 am-12:21 pm

1 stop28h 51m

$655

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mié. 10/22

6:00 am-2:25 pm

1 stop8h 25m

Port of Spain Piarco Intl

mié. 11/5

4:30 pm-12:15 am

1 stop8h 45m

$699

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mar. 10/21

5:48 am-9:20 pm

2 stops15h 32m

Port of Spain Piarco Intl

mar. 10/28

7:00 am-11:16 pm

1 stop16h 16m

$743

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

mar. 10/28

6:20 am-11:23 pm

2 stops17h 03m

Port of Spain Piarco Intl

jue. 10/30

12:30 am-9:38 pm

2 stops21h 08m

$833

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

Best time to book a flight from Chesapeake to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain 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 Port of Spain
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Port of Spain

Get insights into the airlines that provide service to Port of Spain. 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 Port of Spain. Reviews last updated octubre 7, 2025.
Peruse reviews from past customers who have flown with American Airlines from Chesapeake to Port of Spain to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,041 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

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
11,041 reviews
American Airlines
7.2
Good
11,041 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

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 Port of Spain. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Port of Spain from Chesapeake?

    For a flight from Chesapeake to Port of Spain, you will be flying into Piarco Intl. Port of Spain Piarco Intl (POS) is just 12.6 mi from the center of the city. Piarco Intl is the only Port of Spain airport and it handles 0 inbound flights from Chesapeake per day. 1 airline has flights to Port of Spain Piarco Intl from Chesapeake on a regular basis.

  • How long is the flight from Chesapeake to Port of Spain?

    A quick flight from Chesapeake to Port of Spain can take about 17h 08m. United Airlines provides one of the quickest options available for as low as $603. There are 2038 mi between Chesapeake and Port of Spain.

  • Can I find deals for flights from Chesapeake to Port of Spain that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Port of Spain flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Port of Spain?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Port of Spain.

  • Can I find deals for business class flights from Chesapeake to Port of Spain?

    Yes. Cheapflights offers flight deals from Chesapeake to Port of Spain 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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Top airline flying from Chesapeake to Port of Spain

Discover the top airline that operate flights from Chesapeake to Port of Spain. 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 octubre 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$513Average$753FlexibilityNo cancel feeOn-time71%

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