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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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
janv. 26 — févr. 21
dim. 1/26
dim. 2/2
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 janvier 21, 2025.

Round-trip from

$240
(Mytrip)

One-way from

$59
(Frontier)
From Chesapeake to Puerto Rico
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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 janvier 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
mar. 3/47:00 amORF - SJU
2 stops16h 27mSpirit Airlines
mar. 3/115:45 pmSJU - ORF
2 stops25h 30mSpirit Airlines
Deal found 1/20$240
This Delta deal was found by Cheapflights users on 1/21. 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. 3/45:30 amORF - SJU
1 stop10h 37mDelta
jeu. 3/136:15 amSJU - ORF
1 stop9h 02mDelta
Deal found 1/21$245
This Mytrip deal was found by Cheapflights users on 1/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/34:31 pmORF - SJU
1 stop15h 50mMultiple Airlines
mer. 2/510:16 amSJU - ORF
3 stops25h 03mMultiple Airlines
Deal found 1/19$246
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/256:34 pmORF - SJU
1 stop14h 15mFrontier
sam. 3/83:44 amSJU - ORF
1 stop13h 54mFrontier
Deal found 1/20$248
This American Airlines deal was found by Cheapflights users on 1/19. 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.
lun. 2/101:11 pmORF - SJU
2 stops9h 47mAmerican Airlines
mar. 2/116:00 amSJU - ORF
2 stops9h 55mAmerican Airlines
Deal found 1/19$260
This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/256:34 pmORF - BQN
1 stop7h 27mFrontier
lun. 3/33:51 amBQN - ORF
1 stop14h 43mFrontier
Deal found 1/20$260
This United Airlines deal was found by Cheapflights users on 1/20. 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.
lun. 2/36:25 amORF - SJU
1 stop5h 52mUnited Airlines
mer. 8/131:05 amSJU - ORF
1 stop9h 15mUnited Airlines
Deal found 1/20$298
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/13:10 pmORF - SJU
1 stop8h 30mSouthwest
lun. 4/75:35 amSJU - ORF
1 stop5h 55mSouthwest
Deal found 1/20$300
This JetBlue deal was found by Cheapflights users on 1/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/316:00 pmORF - SJU
1 stop7h 20mJetBlue
sam. 6/78:50 amSJU - ORF
1 stop8h 15mJetBlue
Deal found 1/21$388
This United Airlines deal was found by Cheapflights users on 1/20. 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.
jeu. 2/66:35 amORF - BQN
2 stops16h 22mUnited Airlines
dim. 2/91:09 amBQN - ORF
2 stops9h 29mUnited Airlines
Deal found 1/20$396
This Mytrip deal was found by Cheapflights users on 1/20. 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.
lun. 1/274:31 pmORF - CPX
2 stops21h 50mMultiple Airlines
lun. 2/35:41 pmCPX - ORF
3 stops24h 44mMultiple Airlines
Deal found 1/20$571
This Mytrip deal was found by Cheapflights users on 1/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/45:25 amORF - VQS
3 stops36h 05mMultiple Airlines
sam. 2/89:00 amVQS - ORF
3 stops26h 02mMultiple Airlines
Deal found 1/19$680

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 janvier 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 3/4

7:00 am-12:27 am

2 stops16h 27m

San Juan Luis Munoz Marin Intl

mar. 3/11

5:45 pm-7:15 pm

2 stops25h 30m

$240

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 3/4

5:30 am-5:07 pm

1 stop10h 37m

San Juan Luis Munoz Marin Intl

jeu. 3/13

6:15 am-3:17 pm

1 stop9h 02m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 2/3

4:31 pm-9:21 am

1 stop15h 50m

San Juan Luis Munoz Marin Intl

mer. 2/5

10:16 am-10:19 am

3 stops25h 03m

$246

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 2/25

6:34 pm-9:49 am

1 stop14h 15m

San Juan Luis Munoz Marin Intl

sam. 3/8

3:44 am-5:38 pm

1 stop13h 54m

$248

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 2/10

1:11 pm-11:58 pm

2 stops9h 47m

San Juan Luis Munoz Marin Intl

mar. 2/11

6:00 am-2:55 pm

2 stops9h 55m

$260

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

mar. 2/25

6:34 pm-3:01 am

1 stop7h 27m

Aguadilla Borinquen

lun. 3/3

3:51 am-5:34 pm

1 stop14h 43m

$260

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 2/3

6:25 am-1:17 pm

1 stop5h 52m

San Juan Luis Munoz Marin Intl

mer. 8/13

1:05 am-10:20 am

1 stop9h 15m

$298

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 4/1

3:10 pm-11:40 pm

1 stop8h 30m

San Juan Luis Munoz Marin Intl

lun. 4/7

5:35 am-11:30 am

1 stop5h 55m

$300

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

sam. 5/31

6:00 pm-1:20 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

sam. 6/7

8:50 am-5:05 pm

1 stop8h 15m

$388

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

jeu. 2/6

6:35 am-11:57 pm

2 stops16h 22m

Aguadilla Borinquen

dim. 2/9

1:09 am-9:38 am

2 stops9h 29m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 21 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 $378). 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 janvier 21, 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 janvier 21, 2025.
Peruse reviews from past customers who have flown with Spirit Airlines, Frontier and American 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.
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

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.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

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.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

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
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

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 Frontier, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Spirit Airlines 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 - 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 $378). 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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Raleigh to Nassau flights
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Dulles Intl to Port of Spain flights
Raleigh to Montego Bay flights
Dulles Intl to Bridgetown flights
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Dulles Intl to St. John's flights
Richmond to Punta Cana flights
Reagan-National to St. John's flights
Reagan-National to Kingston flights
Richmond to Montego Bay flights
Dulles Intl to St. George's flights
Dulles Intl to Puerto Plata flights
Richmond to Saint Thomas Island flights
Raleigh to Providenciales flights
Raleigh to Santo Domingo flights
Reagan-National to Port of Spain flights
Reagan-National to Puerto Plata flights

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 janvier 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$278FlexibilityNo cancel feeOn-time65%
FrontierCheapest$158Average$285FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$227Average$406FlexibilityNo cancel feeOn-time62%
DeltaCheapest$229Average$390FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$241Average$556FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$247Average$545FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$345Average$500FlexibilityNo cancel feeOn-time63%
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