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Port of Spain

$601+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — POS
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$601
(Mytrip)

Popular in

January

Cheapest in

November

Average price

$935
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 Port of Spain Piarco Intl
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Highest demand for flights based on searches. 19% potential increase in price ($202 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Mytrip deal was found by Cheapflights users on 4/22. 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.
Thu 5/293:11 pmORF - POS
1 stop28h 49mMultiple Airlines
Sun 6/110:10 amPOS - ORF
2 stops31h 13mMultiple Airlines
Deal found 4/22$601
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/2910:30 amORF - POS
2 stops36h 53mUnited Airlines
Mon 6/212:30 amPOS - ORF
3 stops37h 59mUnited Airlines
Deal found 4/22$619
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/295:32 pmORF - POS
2 stops20h 33mAmerican Airlines
Tue 6/33:05 pmPOS - ORF
1 stop8h 23mAmerican Airlines
Deal found 4/22$653

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 April 24, 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

Thu 5/29

3:11 pm-8:00 pm

1 stop28h 49m

Port of Spain Piarco Intl

Sun 6/1

10:10 am-5:23 pm

2 stops31h 13m

$601

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 5/29

10:30 am-11:23 pm

2 stops36h 53m

Port of Spain Piarco Intl

Mon 6/2

12:30 am-2:29 pm

3 stops37h 59m

$619

NorfolkPort of Spain

ORF - POS

ORFPOS

Norfolk

Thu 5/29

5:32 pm-2:05 pm

2 stops20h 33m

Port of Spain Piarco Intl

Tue 6/3

3:05 pm-11:28 pm

1 stop8h 23m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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

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.

Rainfall in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Port of Spain ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Port of Spain when rainfall is around 1.2 in.

Temperature in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Port of Spain, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
United Airlines
7.4
Good
8,685 reviews

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,685 reviews
United Airlines
7.4
Good
8,685 reviews

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,685 reviews

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$536Average$787FlexibilityNo cancel feeOn-time71%

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