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Puerto Rico

$117+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
1 adult, Economy
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Cheap flight deals from Chesapeake to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Puerto Rico (PR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 20, 2024.

Round-trip from

$254
(American Airlines)

One-way from

$117
(American Airlines)
From Chesapeake to Puerto Rico
Search Deals
One-way flight from Chesapeake to Puerto Rico
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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 December 20, 2024.

This American Airlines deal was found by Cheapflights users on 12/19. 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.
Mon 12/236:52 pmORF - SJU
1 stop16h 08mAmerican Airlines
Tue 12/316:05 pmSJU - ORF
1 stop7h 17mAmerican Airlines
Deal found 12/19$518
This Booking.com deal was found by Cheapflights users on 12/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/311:42 pmORF - SJU
1 stop12h 07mMultiple Airlines
Tue 1/711:25 pmSJU - ORF
1 stop10h 25mMultiple Airlines
Deal found 12/19$531
This Frontier deal was found by Cheapflights users on 12/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/229:01 pmORF - SJU
1 stop11h 09mFrontier
Mon 12/306:00 amSJU - ORF
1 stop6h 02mFrontier
Deal found 12/19$593
This eDestinos deal was found by Cheapflights users on 12/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/239:45 amORF - SJU
1 stop14h 40mSpirit Airlines
Thu 1/211:25 pmSJU - ORF
1 stop10h 25mSpirit Airlines
Deal found 12/19$669
This Southwest deal was found by Cheapflights users on 12/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/196:20 amORF - SJU
2 stops9h 30mSouthwest
Sun 12/225:35 amSJU - ORF
2 stops9h 50mSouthwest
Deal found 12/18$764
This United Airlines deal was found by Cheapflights users on 12/19. 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.
Fri 12/208:00 pmORF - SJU
1 stop25h 22mUnited Airlines
Wed 12/255:50 pmSJU - ORF
1 stop6h 40mUnited Airlines
Deal found 12/19$949
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Fri 12/206:00 amORF - BQN
2 stops16h 57mUnited Airlines
Sun 1/51:09 amBQN - ORF
2 stops13h 58mUnited Airlines
Deal found 12/18$1,860

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 December 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 1/30

4:30 pm-11:58 pm

1 stop6h 28m

San Juan Luis Munoz Marin Intl

Tue 2/4

7:45 am-11:52 pm

1 stop17h 07m

$254

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 1/18

4:31 pm-9:21 am

1 stop15h 50m

San Juan Luis Munoz Marin Intl

Wed 1/29

4:53 pm-11:59 pm

3 stops32h 06m

$262

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 1/18

4:31 pm-9:21 am

1 stop15h 50m

San Juan Luis Munoz Marin Intl

Wed 1/29

8:40 pm-9:36 pm

2 stops25h 56m

$268

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 3/26

12:15 pm-10:13 pm

1 stop9h 58m

San Juan Luis Munoz Marin Intl

Tue 4/15

2:04 pm-11:29 pm

1 stop9h 25m

$289

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 3/8

9:05 am-7:12 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Wed 3/12

9:35 pm-4:58 pm

1 stop19h 23m

$298

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

Wed 1/29

6:00 am-11:57 pm

2 stops16h 57m

Aguadilla Borinquen

Mon 2/3

1:09 am-9:38 am

2 stops9h 29m

$344

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 1/29

6:00 am-4:36 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Mon 2/3

2:05 am-10:53 am

1 stop9h 48m

$364

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 3/31

3:20 pm-12:40 am

2 stops9h 20m

San Juan Luis Munoz Marin Intl

Mon 4/14

6:05 am-3:55 pm

1 stop9h 50m

$444

NorfolkCulebra

ORF - CPX

ORFCPX

Norfolk

Thu 2/13

6:15 am-5:21 pm

2 stops10h 06m

Culebra

Sun 2/16

10:48 am-11:36 pm

3 stops13h 48m

$2,444

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 1/13

1:11 pm-11:58 pm

2 stops9h 47m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 15 results
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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 $334). 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 December 20, 2024.

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 December 20, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Frontier and Southwest 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.
Southwest
8.1
Very good
4,821 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,821 reviews
Southwest
8.1
Very good
4,821 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,601 reviews
Southwest
8.1
Very good
4,821 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,041 reviews
Southwest
8.1
Very good
4,821 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,821 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Spirit Airlines
6.3
Okay
8,120 reviews
Southwest
8.1
Very good
4,821 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 American Airlines, with whom users have recently found tickets for as low as $117. However, be on the lookout for offers from Spirit Airlines and Frontier, 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 - Aguadilla Borinquen and Norfolk - Culebra.

  • 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 $334). 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.
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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 December 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$142Average$274FlexibilityNo cancel feeOn-time65%
FrontierCheapest$158Average$285FlexibilityNo cancel feeOn-time62%
DeltaCheapest$227Average$392FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$227Average$409FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$240Average$515FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$247Average$515FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$345Average$494FlexibilityNo cancel feeOn-time63%
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