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$59+ Cheap flights from Chesapeake, VA to Puerto Rico

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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
févr. 25 — mars 41
mar. 2/25
mar. 3/4
1 adult, Economy
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Cheap flight deals from Chesapeake to Puerto Rico

Keep the following information in mind while searching for Chesapeake to Puerto Rico flight deals. Data was last updated février 20, 2025.

Round-trip from

$235
(FlightHub)

One-way from

$59
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$387
From Chesapeake to Puerto Rico
Search Deals
One-way flight from Chesapeake to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chesapeake to Puerto Rico

Cheapest flights from Chesapeake to Puerto Rico
Explore the most affordable flight options available from Chesapeake to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on février 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 4/268:59 pmORF - SJU
2 stops21h 45mSpirit Airlines
dim. 5/410:19 pmSJU - ORF
1 stop13h 03mSpirit Airlines
Deal found 2/19$235
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 3/17:16 pmORF - SJU
1 stop6h 38mFrontier
mer. 3/59:30 pmSJU - ORF
1 stop20h 28mFrontier
Deal found 2/19$238
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/296:55 amORF - SJU
1 stop9h 06mDelta
jeu. 5/85:35 pmSJU - ORF
1 stop6h 26mDelta
Deal found 2/19$245
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 4/258:32 pmORF - SJU
1 stop6h 17mMultiple Airlines
dim. 4/273:52 amSJU - ORF
1 stop7h 30mMultiple Airlines
Deal found 2/19$246
This United Airlines deal was found by Cheapflights users on 2/20. 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.
mer. 10/156:00 amORF - SJU
1 stop7h 45mUnited Airlines
mer. 10/221:05 amSJU - ORF
2 stops8h 30mUnited Airlines
Deal found 2/20$267
This American Airlines deal was found by Cheapflights users on 2/19. 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.
sam. 10/45:50 amORF - SJU
2 stops10h 30mAmerican Airlines
mar. 10/1412:00 pmSJU - ORF
2 stops10h 09mAmerican Airlines
Deal found 2/19$375
This United Airlines deal was found by Cheapflights users on 2/19. 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.
mer. 3/196:10 amORF - BQN
2 stops16h 47mUnited Airlines
mar. 3/2512:09 amBQN - ORF
2 stops9h 33mUnited Airlines
Deal found 2/19$405
This Mytrip deal was found by Cheapflights users on 2/20. 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.
ven. 3/78:32 pmORF - CPX
2 stops12h 50mMultiple Airlines
mar. 3/115:41 pmCPX - ORF
2 stops25h 46mMultiple Airlines
Deal found 2/20$620

Find flights from Chesapeake to Puerto Rico within your budget

Customize your flight search to find flights from Chesapeake to Puerto Rico 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 février 20, 2025.

Fly from

Chesapeake

Fly to

Puerto Rico

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

sam. 4/26

8:59 pm-6:44 pm

2 stops21h 45m

San Juan Luis Munoz Marin Intl

jeu. 5/1

3:52 am-11:22 am

1 stop7h 30m

$235

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

sam. 3/1

7:16 pm-2:54 am

1 stop6h 38m

San Juan Luis Munoz Marin Intl

mer. 3/5

9:30 pm-4:58 pm

1 stop20h 28m

$238

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 4/29

5:30 am-11:40 am

1 stop6h 10m

San Juan Luis Munoz Marin Intl

jeu. 5/1

7:15 am-6:02 pm

1 stop10h 47m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ven. 4/25

8:32 pm-2:49 am

1 stop6h 17m

San Juan Luis Munoz Marin Intl

dim. 4/27

3:52 am-11:22 am

1 stop7h 30m

$246

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 3/25

6:10 am-3:36 pm

1 stop9h 26m

San Juan Luis Munoz Marin Intl

mar. 3/25

1:05 am-2:17 pm

2 stops13h 12m

$330

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

mer. 3/19

6:10 am-10:57 pm

2 stops16h 47m

Aguadilla Borinquen

mar. 3/25

12:09 am-9:42 am

2 stops9h 33m

$405

NorfolkCulebra

ORF - CPX

ORFCPX

Norfolk

ven. 3/7

8:32 pm-10:22 am

2 stops12h 50m

Culebra

mar. 3/11

5:41 pm-7:27 pm

2 stops25h 46m

$620

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mer. 3/26

7:41 pm-1:52 am

1 stop6h 11m

$59

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jeu. 2/27

10:20 am-9:06 pm

1 stop9h 46m

$158

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jeu. 3/13

6:32 am-2:40 pm

2 stops8h 08m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 12 results
1
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Best time to book a flight from Chesapeake to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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.

Travel insights for flights from Chesapeake to Puerto Rico

Get recent, data-driven insights about flights from Chesapeake to Puerto Rico including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chesapeake to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $254). Flying from Chesapeake to Puerto Rico in March is currently the most expensive (average of $363). 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.

What is the cheapest time of day to fly from C6E to PR?

Find hourly flight availability from Chesapeake to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated février 20, 2025.

When flying from Chesapeake to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 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 Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated février 20, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and United Airlines from Chesapeake to Puerto Rico to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,692 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,220 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,766 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Spirit Airlines
6.3
Okay
8,013 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chesapeake to Puerto Rico one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Chesapeake to Puerto Rico for a low price.

  • What are the most popular routes from Chesapeake to Puerto Rico?

    The most popular flight routes from Chesapeake to Puerto Rico are Norfolk - San Juan Luis Munoz Marin Intl, Norfolk - Culebra and Norfolk - Vieques.

  • Can I find deals for flights from Chesapeake to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Puerto Rico?

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

  • Can I find deals for business class flights from Chesapeake to Puerto Rico?

    Yes. Cheapflights offers flight deals from Chesapeake to Puerto Rico 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 Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $254). Flying from Chesapeake to Puerto Rico in March is currently the most expensive (average of $363). 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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Alternative routes for Chesapeake to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Luis Munoz Marin Intl flights
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Richmond to Punta Cana flights
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Dulles Intl to St. George's flights
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Top 7 airlines flying from Chesapeake to Puerto Rico

Discover the top 7 airlines that operate flights from Chesapeake to Puerto Rico. 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 février 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$279FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$161Average$284FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$224Average$407FlexibilityNo cancel feeOn-time62%
DeltaCheapest$232Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$237Average$506FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$527FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$344Average$507FlexibilityNo cancel feeOn-time63%
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