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Puerto Rico

$104+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
jun 17 — jun 241
ter 6/17
ter 6/24
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 junho 12, 2025.

Round-trip from

$255
(Delta)

One-way from

$104
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$448
From Chesapeake to Puerto Rico
Search Deals
One-way flight from Chesapeake to Puerto Rico
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junho 12, 2025.

This CheapOair deal was found by Cheapflights users on 6/11. 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.
dom 8/102:03 pmORF - SJU
1 stop19h 01mFrontier
sáb 8/238:13 pmSJU - ORF
1 stop24h 54mFrontier
Deal found 6/11$259
This FlightHub deal was found by Cheapflights users on 6/11. 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.
qui 8/77:39 pmORF - BQN
1 stop14h 42mFrontier
qua 8/273:39 amBQN - ORF
1 stop17h 28mFrontier
Deal found 6/11$263
This Mytrip deal was found by Cheapflights users on 6/11. 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.
qui 7/179:05 amORF - SJU
1 stop12h 04mMultiple Airlines
sex 7/181:37 amSJU - ORF
2 stops30h 38mMultiple Airlines
Deal found 6/11$264
This CheapOair deal was found by Cheapflights users on 6/11. 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.
qui 8/215:30 amORF - SJU
1 stop16h 13mSpirit Airlines
seg 8/255:57 pmSJU - ORF
1 stop28h 52mSpirit Airlines
Deal found 6/11$275
This American Airlines deal was found by Cheapflights users on 6/11. 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.
seg 11/108:26 pmORF - SJU
1 stop14h 19mAmerican Airlines
qui 11/136:30 amSJU - ORF
2 stops9h 13mAmerican Airlines
Deal found 6/11$278
This Southwest deal was found by Cheapflights users on 6/10. 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.
qua 9/103:45 pmORF - SJU
1 stop7h 00mSouthwest
dom 9/215:45 amSJU - ORF
1 stop11h 45mSouthwest
Deal found 6/10$305
This Delta deal was found by Cheapflights users on 6/11. 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.
seg 8/187:00 amORF - SJU
1 stop9h 27mDelta
qua 8/277:00 amSJU - ORF
1 stop10h 54mDelta
Deal found 6/11$340
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 9/166:00 amORF - SJU
1 stop7h 45mUnited Airlines
seg 9/221:05 amSJU - ORF
2 stops13h 35mUnited Airlines
Deal found 6/12$345
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 6/1410:21 amORF - BQN
2 stops15h 38mMultiple Airlines
dom 6/292:59 amBQN - ORF
1 stop9h 57mMultiple Airlines
Deal found 6/11$701
This United Airlines deal was found by Cheapflights users on 6/10. 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.
dom 7/610:31 amORF - BQN
2 stops12h 38mUnited Airlines
qui 7/1012:15 amBQN - ORF
2 stops9h 26mUnited Airlines
Deal found 6/10$745

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 junho 12, 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

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

qua 7/23

1:48 pm-10:23 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

qua 8/6

7:30 am-3:30 pm

1 stop8h 00m

$255

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

qui 7/17

7:39 pm-12:32 am

1 stop28h 53m

San Juan Luis Munoz Marin Intl

qua 7/30

1:37 am-5:35 pm

1 stop15h 58m

$256

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom 8/10

2:03 pm-9:04 am

1 stop19h 01m

San Juan Luis Munoz Marin Intl

sáb 8/23

8:13 pm-9:07 pm

1 stop24h 54m

$259

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

qui 8/7

7:39 pm-10:21 am

1 stop14h 42m

Aguadilla Borinquen

qua 8/27

3:39 am-9:07 pm

1 stop17h 28m

$263

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

qui 8/21

5:30 am-9:43 pm

1 stop16h 13m

San Juan Luis Munoz Marin Intl

seg 8/25

5:57 pm-10:49 pm

1 stop28h 52m

$275

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

seg 11/10

7:03 pm-5:05 am

1 stop9h 02m

San Juan Luis Munoz Marin Intl

qui 11/13

6:30 am-2:43 pm

2 stops9h 13m

$278

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

qua 9/10

3:45 pm-10:45 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

dom 9/21

5:45 am-5:30 pm

1 stop11h 45m

$305

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ter 9/16

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

seg 10/6

1:05 am-9:37 am

2 stops8h 32m

$345

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

dom 7/6

10:31 am-11:09 pm

2 stops12h 38m

Aguadilla Borinquen

qui 7/10

12:15 am-9:41 am

2 stops9h 26m

$745

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom 6/29

9:05 am-7:19 pm

1 stop10h 14m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 17 results
1
2

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, 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 June is currently the most expensive (average of $339). 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 junho 12, 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 junho 12, 2025.
Peruse reviews from past customers who have flown with Southwest, 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.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Spirit Airlines
6.3
Okay
8,052 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $107. However, be on the lookout for offers from Spirit Airlines and Delta, 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 - 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 June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

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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 junho 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$207FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$286FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$412FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$224Average$494FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$378FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$541FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$346Average$535FlexibilityNo cancel feeOn-time63%

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