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Puerto Rico

$128+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
may. 4 — may. 111
dom. 5/4
dom. 5/11
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 abril 29, 2025.

Round-trip from

$245
(Delta)

One-way from

$128
(Delta)

Popular in

December

Cheapest in

July

Average price

$459
From Chesapeake to Puerto Rico
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One-way flight from Chesapeake to Puerto Rico
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Highest demand for flights based on searches. 11% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 29, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/167:00 amORF - SJU
1 stop9h 18mDelta
mar. 9/237:00 amSJU - ORF
1 stop9h 48mDelta
Deal found 4/28$245
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/2812:13 pmORF - SJU
1 stop12h 41mSpirit Airlines
lun. 6/28:12 pmSJU - ORF
2 stops14h 17mSpirit Airlines
Deal found 4/29$251
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/208:32 amORF - SJU
2 stops11h 38mAmerican Airlines
sáb. 9/273:55 pmSJU - ORF
1 stop16h 23mAmerican Airlines
Deal found 4/28$265
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/124:11 pmORF - SJU
1 stop27h 08mMultiple Airlines
dom. 6/159:30 amSJU - ORF
1 stop28h 59mMultiple Airlines
Deal found 4/28$310
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/223:28 pmORF - SJU
1 stop8h 53mFrontier
dom. 5/256:00 amSJU - ORF
1 stop8h 33mFrontier
Deal found 4/29$318
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/166:30 amORF - SJU
1 stop8h 14mUnited Airlines
lun. 10/61:05 amSJU - ORF
2 stops13h 35mUnited Airlines
Deal found 4/29$335
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/293:28 pmORF - BQN
1 stop10h 29mFrontier
mié. 6/42:59 amBQN - ORF
1 stop6h 54mFrontier
Deal found 4/29$378
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/65:09 pmORF - BQN
1 stop8h 48mMultiple Airlines
lun. 5/122:47 amBQN - ORF
1 stop7h 42mMultiple Airlines
Deal found 4/29$383
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/14:00 pmORF - SJU
1 stop7h 25mSouthwest
sáb. 7/55:00 amSJU - ORF
1 stop11h 00mSouthwest
Deal found 4/28$454
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/61:00 pmORF - BQN
2 stops10h 09mUnited Airlines
lun. 5/1212:15 amBQN - ORF
2 stops14h 16mUnited Airlines
Deal found 4/29$505
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/1412:13 pmORF - CPX
3 stops29h 08mMultiple Airlines
dom. 5/1810:48 amCPX - ORF
2 stops23h 41mMultiple Airlines
Deal found 4/29$560

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 abril 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

mié. 5/28

12:13 pm-12:54 am

1 stop12h 41m

San Juan Luis Munoz Marin Intl

lun. 6/2

8:12 pm-10:29 am

2 stops14h 17m

$251

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jue. 5/29

4:21 pm-11:42 pm

1 stop7h 21m

San Juan Luis Munoz Marin Intl

jue. 6/5

1:12 pm-11:02 pm

1 stop9h 50m

$255

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 6/2

10:26 am-9:17 pm

2 stops34h 51m

San Juan Luis Munoz Marin Intl

vie. 6/6

8:12 pm-4:35 pm

1 stop20h 23m

$258

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mié. 5/21

8:24 pm-1:20 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

mié. 5/28

11:50 am-11:28 pm

1 stop11h 38m

$303

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jue. 5/22

3:28 pm-2:32 am

1 stop11h 04m

San Juan Luis Munoz Marin Intl

dom. 5/25

6:00 am-2:33 pm

1 stop8h 33m

$318

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

jue. 5/29

3:28 pm-1:57 am

1 stop10h 29m

Aguadilla Borinquen

mié. 6/4

2:59 am-9:53 am

1 stop6h 54m

$378

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

mar. 5/6

5:09 pm-1:57 am

1 stop8h 48m

Aguadilla Borinquen

lun. 5/12

2:47 am-10:29 am

1 stop7h 42m

$383

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

vie. 5/9

6:25 am-5:45 pm

2 stops11h 20m

San Juan Luis Munoz Marin Intl

lun. 5/12

7:40 am-6:45 pm

2 stops11h 05m

$497

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jue. 5/29

6:15 am-1:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

mié. 6/4

1:05 am-9:41 am

2 stops8h 36m

$505

NorfolkAguadilla

ORF - BQN

ORFBQN

Norfolk

mar. 5/6

1:00 pm-11:09 pm

2 stops10h 09m

Aguadilla Borinquen

lun. 5/12

12:15 am-2:31 pm

2 stops14h 16m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 18 results
1
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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, 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 December is currently the most expensive (average of $336). 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 abril 29, 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 abril 29, 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
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Spirit Airlines
6.3
Okay
7,956 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Delta, with whom users have recently found tickets for as low as $128. However, be on the lookout for offers from Frontier 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 - Vieques and Norfolk - Aguadilla Borinquen.

  • 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 December is currently the most expensive (average of $336). 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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Reagan-National to Kingston flights
Reagan-National to Christiansted flights
Dulles Intl to Christiansted flights
Richmond to Simpson Bay 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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$163Average$283FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$224Average$498FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$224Average$410FlexibilityNo cancel feeOn-time62%
DeltaCheapest$234Average$375FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$562FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$345Average$519FlexibilityNo cancel feeOn-time63%

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