Puerto Rico

$68+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Mar 21 — Mar 281
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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 February 19, 2026.

This Delta deal was found by Cheapflights users on 2/16. 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.
Tue 4/147:00 am
ORF
-
SJU
1 stop6h 25m
Delta
Tue 4/216:15 am
SJU
-
ORF
1 stop6h 42m
Delta
Deal found 2/16$206
This CheapOair deal was found by Cheapflights users on 2/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/131:50 pm
ORF
-
SJU
Nonstop3h 30m
Multiple Airlines
Sat 4/188:00 am
SJU
-
ORF
1 stop9h 49m
Multiple Airlines
Deal found 2/18$208
This Priceline deal was found by Cheapflights users on 2/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:43 pm
ORF
-
SJU
1 stop7h 15m
Multiple Airlines
Sun 3/298:15 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/15$209
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.
Thu 4/238:41 pm
ORF
-
SJU
1 stop26h 07m
Frontier
Wed 4/293:21 am
SJU
-
ORF
1 stop16h 25m
Frontier
Deal found 2/19$210
This CheapOair deal was found by Cheapflights users on 2/16. 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.
Sun 5/106:43 pm
ORF
-
SJU
1 stop7h 18m
Multiple Airlines
Mon 5/189:00 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/16$212
This Priceline deal was found by Cheapflights users on 2/17. 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.
Mon 4/276:43 pm
ORF
-
SJU
1 stop7h 18m
Frontier
Sat 5/28:00 am
SJU
-
ORF
1 stop9h 49m
Frontier
Deal found 2/17$213
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Tue 3/316:06 am
ORF
-
SJU
1 stop16h 52m
American Airlines
Tue 4/146:00 am
SJU
-
ORF
1 stop11h 00m
American Airlines
Deal found 2/16$215
This Frontier deal was found by Cheapflights users on 2/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/233:26 pm
ORF
-
BQN
1 stop10h 16m
Frontier
Tue 3/312:43 am
BQN
-
ORF
1 stop12h 00m
Frontier
Deal found 2/15$216
This CheapOair deal was found by Cheapflights users on 2/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:43 pm
ORF
-
SJU
1 stop7h 18m
Multiple Airlines
Mon 5/119:00 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/18$217
This KAYAK deal was found by Cheapflights users on 2/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2310:04 am
ORF
-
SJU
1 stop7h 47m
JetBlue
Wed 4/19:00 am
SJU
-
ORF
Nonstop3h 41m
JetBlue
Deal found 2/15$222
This United Airlines deal was found by Cheapflights users on 2/17. 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.
Mon 4/276:00 am
ORF
-
SJU
1 stop8h 44m
United Airlines
Fri 5/11:00 am
SJU
-
ORF
2 stops8h 31m
United Airlines
Deal found 2/17$224
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:03 am
ORF
-
SJU
1 stop9h 28m
Delta
Fri 4/242:45 pm
SJU
-
ORF
1 stop7h 48m
Delta
Deal found 2/18$226

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 February 19, 2026.

Round-trip from

$206
(Delta)

One-way from

$68
(SmartFares)

Popular in

December

Cheapest in

September

Average price

$378
From Chesapeake to Puerto Rico
One-way flight from Chesapeake to Puerto Rico
Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 19, 2026.
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

Sat 4/18

2:03 pm-8:24 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

Wed 4/22

5:34 pm-12:37 am

1 stop7h 03m

$206

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 4/27

6:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Thu 4/30

1:00 am-9:31 am

2 stops8h 31m

$224

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 4/27

5:50 am-4:23 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:15 am-5:17 pm

1 stop10h 02m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 4/26

7:03 am-4:31 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:15 am-5:17 pm

1 stop10h 02m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 3/31

5:50 am-11:46 am

1 stop5h 56m

San Juan Luis Munoz Marin Intl

Tue 4/7

7:30 am-4:08 pm

1 stop8h 38m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 4/28

5:45 am-12:52 pm

1 stop7h 07m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:15 am-5:17 pm

1 stop10h 02m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 5/3

7:03 am-4:31 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:15 am-5:17 pm

1 stop10h 02m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 5/3

7:03 am-4:31 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Thu 5/7

6:15 am-12:58 pm

1 stop6h 43m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 4/29

7:03 am-4:31 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:15 am-5:17 pm

1 stop10h 02m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 4/29

7:03 am-4:31 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Sat 5/2

5:34 pm-12:37 am

1 stop7h 03m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/15

Showing 1-10 of 43 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, July is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $119). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $259). 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.

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 February 19, 2026.
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.

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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 Delta, United Airlines, and Frontier fly from Chesapeake to Puerto Rico in about 6h 26m. The time it takes to get you to your destination can typically vary by up to 2h 18m. 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 $77. However, be on the lookout for offers from Southwest and Spirit 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?

  • What are the cheapest flights from Chesapeake to Puerto Rico?

    While on average a flight from Chesapeake to Puerto Rico is generally $438, our data shows the cheapest flight currently is $265. When looking at the most popular route, (Norfolk - San Juan Luis Munoz Marin Intl), you can expect to pay $128 for that flight.

  • 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, July is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $119). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $259). 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.

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 February 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$94Average$326FlexibilityNo cancel feeOn-time65%
FrontierCheapest$110Average$289FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$373FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$191Average$483FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$442FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$205Average$485FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$521FlexibilityNo cancel feeOn-time71%

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