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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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
nov 28 — dez 51
sex 11/28
sex 12/5
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 outubro 29, 2025.

Round-trip from

$225
(United Airlines)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$361
From Chesapeake to Puerto Rico
Search Deals
One-way flight from Chesapeake to Puerto Rico
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 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 October 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 outubro 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
qui 11/277:18 pmORF - SJU
1 stop27h 26mMultiple Airlines
sáb 12/68:00 amSJU - ORF
1 stop15h 03mMultiple Airlines
Deal found 10/28$269
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
qua 11/269:26 pmORF - SJU
1 stop22h 46mMultiple Airlines
sáb 12/68:00 amSJU - ORF
1 stop15h 03mMultiple Airlines
Deal found 10/28$273
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sex 11/218:02 pmORF - SJU
1 stop26h 27mMultiple Airlines
dom 11/233:59 amSJU - ORF
1 stop6h 44mMultiple Airlines
Deal found 10/28$278
This American Airlines deal was found by Cheapflights users on 10/29. 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.
sex 11/146:00 amORF - SJU
2 stops10h 05mAmerican Airlines
qua 11/196:25 amSJU - ORF
1 stop14h 35mAmerican Airlines
Deal found 10/29$290
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
dom 11/239:26 pmORF - SJU
1 stop13h 12mMultiple Airlines
seg 11/243:59 amSJU - ORF
1 stop17h 32mMultiple Airlines
Deal found 10/28$294
This Priceline deal was found by Cheapflights users on 10/29. 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.
qui 11/132:00 pmORF - SJU
1 stop11h 54mFrontier
sáb 11/153:59 amSJU - ORF
1 stop9h 17mFrontier
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sex 11/219:26 pmORF - SJU
1 stop12h 20mMultiple Airlines
sáb 11/223:59 amSJU - ORF
1 stop10h 16mMultiple Airlines
Deal found 10/28$299
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
qua 11/269:26 pmORF - SJU
1 stop22h 46mMultiple Airlines
qua 12/39:15 amSJU - ORF
2 stops47h 28mMultiple Airlines
Deal found 10/29$300
This Delta deal was found by Cheapflights users on 10/27. 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.
ter 12/27:00 amORF - SJU
1 stop9h 20mDelta
qua 12/101:57 pmSJU - ORF
1 stop11h 35mDelta
Deal found 10/27$301
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
qui 11/132:00 pmORF - BQN
1 stop12h 04mMultiple Airlines
dom 11/163:59 amBQN - ORF
1 stop9h 25mMultiple Airlines
Deal found 10/29$423
This United Airlines deal was found by Cheapflights users on 10/26. 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 12/910:36 amORF - BQN
3 stops12h 21mUnited Airlines
qua 12/171:09 amBQN - ORF
2 stops9h 46mUnited Airlines
Deal found 10/26$450
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
sáb 11/810:05 pmORF - BQN
2 stops27h 59mMultiple Airlines
qua 11/123:59 amBQN - ORF
1 stop10h 16mMultiple Airlines
Deal found 10/28$499

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 outubro 29, 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

ter 3/3

5:30 am-5:12 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

qui 3/5

6:15 am-2:00 pm

1 stop8h 45m

$247

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

seg 1/26

5:20 am-1:05 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

sex 1/30

6:27 pm-12:16 am

1 stop6h 49m

$247

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

qui 1/8

7:00 am-4:49 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

sex 1/16

2:15 pm-9:30 pm

1 stop8h 15m

$247

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

dom 2/8

10:05 am-11:57 pm

2 stops12h 52m

Aguadilla Borinquen

sáb 2/14

1:09 am-2:23 pm

2 stops14h 14m

$250

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom 1/25

6:05 am-1:17 pm

1 stop6h 12m

San Juan Luis Munoz Marin Intl

sex 1/30

2:05 am-2:25 pm

2 stops13h 20m

$264

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

seg 1/19

10:05 am-10:22 pm

2 stops11h 17m

San Juan Luis Munoz Marin Intl

ter 1/20

2:05 am-2:25 pm

2 stops13h 20m

$300

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ter 12/2

7:00 am-5:20 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

qua 12/10

1:57 pm-12:32 am

1 stop11h 35m

$301

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom 2/1

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

sex 2/6

2:05 am-2:25 pm

2 stops13h 20m

$315

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

sáb 1/24

10:05 am-11:57 pm

2 stops12h 52m

Aguadilla Borinquen

dom 2/1

1:09 am-9:52 am

2 stops9h 43m

$315

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

seg 1/26

4:12 pm-11:57 pm

1 stop6h 45m

Aguadilla Borinquen

sáb 1/31

1:09 am-2:25 pm

2 stops14h 16m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 36 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 $109). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $236). 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 outubro 29, 2025.

Unlike at noon, 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. Wednesday at noon 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 outubro 29, 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
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 and United Airlines 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 3h 57m. The distance between Chesapeake and Puerto Rico is about 1384 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $109). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $236). 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 outubro 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$164Average$297FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$522FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$378FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$419FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$242Average$531FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$510FlexibilityNo cancel feeOn-time63%

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