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Puerto Rico

$113+ 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
janv. 14 — janv. 211
mer. 1/14
mer. 1/21
1 adult, Economy
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Cheap 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 décembre 15, 2025.

This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/222:04 pmORF - SJU
1 stop8h 34mFrontier
jeu. 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/14$284
This Priceline deal was found by Cheapflights users on 12/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/233:11 pmORF - SJU
1 stop28h 16mFrontier
mer. 1/79:23 pmSJU - ORF
1 stop17h 11mFrontier
Deal found 12/14$343
This Orbitz deal was found by Cheapflights users on 12/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/233:11 pmORF - SJU
1 stop10h 39mMultiple Airlines
mer. 1/71:55 amSJU - ORF
2 stops17h 43mMultiple Airlines
Deal found 12/13$351
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 12/213:09 pmORF - SJU
1 stop10h 41mFrontier
jeu. 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/13$353
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/203:01 pmORF - SJU
1 stop10h 49mFrontier
dim. 12/216:00 amSJU - ORF
1 stop9h 14mFrontier
Deal found 12/13$354
This Priceline deal was found by Cheapflights users on 12/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 12/213:09 pmORF - SJU
1 stop7h 34mFrontier
mer. 1/79:23 pmSJU - ORF
1 stop17h 11mFrontier
Deal found 12/14$373
This Booking.com deal was found by Cheapflights users on 12/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/158:38 amORF - SJU
1 stop14h 38mMultiple Airlines
lun. 12/229:37 pmSJU - ORF
1 stop17h 39mMultiple Airlines
Deal found 12/14$379
This Priceline deal was found by Cheapflights users on 12/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/223:01 pmORF - SJU
1 stop6h 04mMultiple Airlines
mer. 1/79:23 pmSJU - ORF
1 stop17h 11mMultiple Airlines
Deal found 12/14$381
This Booking.com deal was found by Cheapflights users on 12/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/292:04 pmORF - SJU
1 stop8h 34mFrontier
sam. 1/106:18 pmSJU - ORF
1 stop20h 16mFrontier
Deal found 12/12$382
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/168:11 pmORF - SJU
1 stop22h 49mMultiple Airlines
dim. 12/217:35 amSJU - ORF
1 stop7h 31mMultiple Airlines
Deal found 12/13$384
This United Airlines deal was found by Cheapflights users on 12/14. 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.
mer. 12/176:05 amORF - SJU
2 stops15h 17mUnited Airlines
mer. 12/245:50 pmSJU - ORF
1 stop6h 51mUnited Airlines
Deal found 12/14$386
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/3111:44 amORF - BQN
2 stops14h 26mMultiple Airlines
lun. 1/56:42 pmBQN - ORF
1 stop25h 03mMultiple Airlines
Deal found 12/15$522

Find 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 décembre 15, 2025.

Round-trip from

$166
(Priceline)

One-way from

$113
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$583
From Chesapeake to Puerto Rico
Search Deals
One-way flight from Chesapeake to Puerto Rico
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
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 décembre 15, 2025.
Use the filters below to find and compare flights from Chesapeake to Puerto Rico that are best for you.

Fly from

Chesapeake

Fly to

Puerto Rico

Route

Depart

Return

Price

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

lun. 1/26

10:05 am-11:57 pm

2 stops12h 52m

Aguadilla Borinquen

sam. 1/31

1:09 am-2:25 pm

2 stops14h 16m

$225

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

dim. 2/22

3:26 pm-2:57 am

1 stop10h 31m

Aguadilla Borinquen

sam. 2/28

3:58 am-2:41 pm

1 stop11h 43m

$250

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 1/13

5:20 am-1:05 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

jeu. 1/22

6:27 pm-12:16 am

1 stop6h 49m

$285

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ven. 2/6

7:01 am-4:50 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

lun. 2/9

6:27 pm-12:16 am

1 stop6h 49m

$285

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ven. 2/6

7:01 am-4:50 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

jeu. 2/12

3:55 pm-10:23 pm

1 stop7h 28m

$285

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dim. 2/15

6:45 am-11:09 pm

1 stop15h 24m

San Juan Luis Munoz Marin Intl

mar. 2/17

4:36 pm-6:26 pm

1 stop26h 50m

$291

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 1/12

10:05 am-12:36 am

2 stops13h 31m

San Juan Luis Munoz Marin Intl

jeu. 1/22

8:35 am-6:53 pm

2 stops11h 18m

$297

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ven. 5/1

1:50 pm-5:20 pm

Nonstop3h 30m

San Juan Luis Munoz Marin Intl

lun. 5/4

9:00 am-12:50 pm

Nonstop3h 50m

$298

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 1/27

8:50 am-7:05 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

jeu. 1/29

6:10 am-4:45 pm

2 stops11h 35m

$299

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jeu. 2/5

6:45 am-7:26 pm

2 stops11h 41m

San Juan Luis Munoz Marin Intl

jeu. 2/12

12:00 pm-6:28 pm

1 stop7h 28m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 37 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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Puerto Rico

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

Currently, May is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $113). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $275). 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 décembre 15, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 12% on flights from Chesapeake to Puerto Rico by exploring options for tickets in the evening.

What is the cheapest day to fly from Chesapeake to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Puerto Rico. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Puerto Rico flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 décembre 15, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chesapeake to Puerto Rico have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,185 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chesapeake to Puerto Rico?

    Airlines like United Airlines, Frontier, and Delta fly from Chesapeake to Puerto Rico in about 6h 45m. The time it takes to get you to your destination can typically vary by up to 6h 07m. The distance between Chesapeake and Puerto Rico is about 1416 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $84. However, be on the lookout for offers from Spirit Airlines and Southwest, 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, May is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $113). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $275). 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 décembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$154Average$297FlexibilityNo cancel feeOn-time65%
DeltaCheapest$212Average$379FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$479FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$521FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$241Average$426FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$250Average$499FlexibilityNo cancel feeOn-time63%

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