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Port of Spain

$217+ Cheap flights from Chesapeake, VA to Port of Spain (POS)

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$540
(United Airlines)

One-way from

$217
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$866
From Chesapeake to Port of Spain Piarco Intl
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One-way flight from Chesapeake to Port of Spain Piarco Intl
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Highest demand for flights based on searches. 17% potential increase in price ($185 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 10/206:00 amORF - POS
2 stops17h 23mUnited Airlines
Wed 12/171:30 amPOS - ORF
2 stops21h 25mUnited Airlines
Deal found 9/14$540
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 10/206:00 amORF - POS
1 stop8h 25mAmerican Airlines
Thu 12/184:46 pmPOS - ORF
1 stop9h 13mAmerican Airlines
Deal found 9/14$618
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/210:33 amORF - POS
2 stops12h 50mUnited Airlines
Wed 10/812:30 amPOS - ORF
2 stops21h 08mUnited Airlines
Deal found 9/14$648
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/14$738
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/16:30 amORF - POS
2 stops16h 53mUnited Airlines
Tue 10/712:30 amPOS - ORF
2 stops34h 12mUnited Airlines
Deal found 9/14$758
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/26:15 amORF - POS
1 stop8h 01mAmerican Airlines
Thu 10/97:00 amPOS - ORF
1 stop16h 16mAmerican Airlines
Deal found 9/14$788
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Sun 9/286:15 amORF - POS
1 stop17h 08mUnited Airlines
Mon 9/2912:30 amPOS - ORF
2 stops23h 00mUnited Airlines
Deal found 9/13$853

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 September 15, 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

Mon 10/20

6:00 am-11:23 pm

2 stops17h 23m

Port of Spain Piarco Intl

Wed 12/17

1:30 am-9:55 pm

2 stops21h 25m

$540

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Mon 10/20

5:00 am-9:20 pm

2 stops16h 20m

Port of Spain Piarco Intl

Thu 12/18

6:02 am-11:01 pm

2 stops17h 59m

$623

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 10/2

10:33 am-11:23 pm

2 stops12h 50m

Port of Spain Piarco Intl

Wed 10/8

12:30 am-9:38 pm

2 stops21h 08m

$648

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

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 10/2

5:30 pm-2:16 pm

2 stops20h 46m

Port of Spain Piarco Intl

Thu 10/9

7:00 am-11:16 pm

1 stop16h 16m

$743

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Wed 10/1

6:15 am-11:23 pm

1 stop17h 08m

Port of Spain Piarco Intl

Tue 10/7

12:30 am-9:37 pm

2 stops21h 07m

$758

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Sat 1/3

7:20 pm-3:46 pm

2 stops19h 26m

Port of Spain Piarco Intl

Thu 1/8

7:10 am-10:48 pm

2 stops16h 38m

$763

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 10/2

5:20 am-1:46 am

2 stops20h 26m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 September 15, 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
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Crew

8.0

Entertainment

6.9

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

Crew

8.0

Entertainment

6.9

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 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 16h 20m. United Airlines provides one of the quickest options available for as low as $623. There are 2038 mi between Chesapeake and Port of Spain. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

  • What is the cheapest month to book a flight from Chesapeake to Port of Spain?

    Currently, October is the cheapest month in which you can book a flight from Chesapeake to Port of Spain (average of $435). Flying from Chesapeake to Port of Spain 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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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$513Average$758FlexibilityNo cancel feeOn-time71%

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