HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Port of Spain

$544+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
Mar 19 — Mar 261
Thu 3/19
Thu 3/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Port of Spain with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 February 17, 2026.

This United Airlines deal was found by Cheapflights users on 2/13. 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.
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 2/13$544
This United Airlines deal was found by Cheapflights users on 2/14. 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 7/136:15 am
ORF
-
POS
1 stop17h 08m
United Airlines
Mon 7/202:00 am
POS
-
ORF
2 stops12h 11m
United Airlines
Deal found 2/14$571
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 United Airlines deal was found by Cheapflights users on 2/12. 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 3/217:45 pm
ORF
-
POS
2 stops27h 38m
United Airlines
Tue 3/2412:30 am
POS
-
ORF
2 stops23h 04m
United Airlines
Deal found 2/12$674
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Sat 3/147:45 pm
ORF
-
POS
2 stops27h 38m
United Airlines
Fri 3/2012:30 am
POS
-
ORF
2 stops20h 24m
United Airlines
Deal found 2/14$694
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Sat 3/146:06 am
ORF
-
POS
1 stop8h 04m
American Airlines
Sat 3/213:10 pm
POS
-
ORF
1 stop8h 41m
American Airlines
Deal found 2/14$730

Find 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 February 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$544
(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 February 17, 2026.
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

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

$544

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Mon 7/13

6:10 am-11:23 pm

2 stops17h 13m

Port of Spain Piarco Intl

Mon 7/20

2:00 am-3:14 pm

2 stops13h 14m

$544

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Tue 8/11

6:29 am-2:24 pm

1 stop7h 55m

Port of Spain Piarco Intl

Tue 8/18

7:00 am-11:42 pm

1 stop16h 42m

$610

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

Wed 4/15

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

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 February 17, 2026.
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
11,294 reviews

Crew

8.0

Entertainment

6.9

Boarding

7.5

Food

6.4

Comfort

7.2

Overall

7.2

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
11,294 reviews
American Airlines
7.2
Good
11,294 reviews

Crew

8.0

Entertainment

6.9

Boarding

7.5

Food

6.4

Comfort

7.2

Overall

7.2

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 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 7h 55m. United Airlines provides one of the quickest options available for as low as $610. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$549Average$758FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights