San Juan

$117+ Cheap flights from Chesapeake, VA to San Juan

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 27 — Jan 31
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The best prices from Chesapeake to San Juan are usually found in July or September, booked 19 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chesapeake to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$254
(Delta)

One-way from

$117
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$564
From Chesapeake to San Juan
One-way flight from Chesapeake to San Juan
High demand for flights, 11% potential price rise
Best time to find cheap flights, 4% potential price drop
Average for round-trip flights in December 2024

Find flight deals from Chesapeake to San Juan

Cheapest flights from Chesapeake to San Juan
Explore the most affordable flight options available from Chesapeake to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 22, 2024.

This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/299:01 pmORF - SJU
2 stops50h 58mMultiple Airlines
Sat 1/1111:55 amSJU - ORF
1 stop21h 44mMultiple Airlines
Deal found 12/21$485
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/298:00 pmORF - SJU
1 stop16h 34mAmerican Airlines
Sat 1/116:00 amSJU - ORF
1 stop10h 22mAmerican Airlines
Deal found 12/21$509
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/319:45 amORF - SJU
1 stop14h 40mSpirit Airlines
Sun 1/511:25 pmSJU - ORF
1 stop10h 25mSpirit Airlines
Deal found 12/22$563
This Frontier deal was found by Cheapflights users on 12/22. 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.
Sun 12/299:01 pmORF - SJU
1 stop11h 09mFrontier
Wed 1/13:54 amSJU - ORF
1 stop9h 48mFrontier
Deal found 12/22$578
This Southwest deal was found by Cheapflights users on 12/21. 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.
Mon 12/2310:05 amORF - SJU
2 stops11h 10mSouthwest
Mon 12/306:10 amSJU - ORF
1 stop9h 15mSouthwest
Deal found 12/21$801
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/296:00 amORF - SJU
1 stop15h 22mUnited Airlines
Fri 1/102:05 amSJU - ORF
2 stops13h 38mUnited Airlines
Deal found 12/21$816
This Delta deal was found by Cheapflights users on 12/21. 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 12/246:00 amORF - SJU
1 stop10h 15mDelta
Mon 12/306:30 amSJU - ORF
1 stop11h 28mDelta
Deal found 12/21$871

Find flights from Chesapeake to San Juan within your budget

Customize your flight search to find flights from Chesapeake to San Juan 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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 1/12

7:05 am-4:55 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Sat 1/25

6:15 am-3:35 pm

1 stop10h 20m

$254

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 1/12

5:25 am-12:59 am

1 stop18h 34m

San Juan Luis Munoz Marin Intl

Fri 1/17

10:09 pm-3:36 pm

1 stop18h 27m

$256

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 2/8

4:31 pm-9:21 am

1 stop15h 50m

San Juan Luis Munoz Marin Intl

Sat 2/15

7:00 am-6:15 pm

1 stop12h 15m

$258

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 1/13

3:52 pm-11:58 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Thu 1/16

2:35 pm-10:24 pm

2 stops8h 49m

$274

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 1/22

6:10 am-10:22 pm

3 stops15h 12m

San Juan Luis Munoz Marin Intl

Thu 1/23

7:45 am-11:26 pm

2 stops16h 41m

$318

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 3/2

6:12 pm-9:35 am

1 stop14h 23m

San Juan Luis Munoz Marin Intl

Sat 3/8

3:44 am-5:28 pm

1 stop13h 44m

$417

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 3/5

2:10 pm-12:25 am

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Sun 3/9

5:35 am-4:05 pm

1 stop10h 30m

$435

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 3/11

6:16 am-8:24 pm

1 stop14h 08m

$117

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 1/4

6:00 am-8:22 pm

1 stop13h 22m

$133

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 12/31

12:29 pm-9:12 pm

1 stop7h 43m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 12 results
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Best time to book a flight from Chesapeake to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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.

Travel insights for flights from Chesapeake to San Juan

Get recent, data-driven insights about flights from Chesapeake to San Juan including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chesapeake to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to San Juan. Price data was last updated on December 20, 2024.

Booking 19 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chesapeake to San Juan. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chesapeake to San Juan?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to San Juan (average of $254). Flying from Chesapeake to San Juan in March is currently the most expensive (average of $380). 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 SJU?

Find hourly flight availability from Chesapeake to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 22, 2024.

When flying from Chesapeake to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chesapeake to San Juan?

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

Travelers seeking maximum savings on their Chesapeake to San Juan flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in San Juan by month

Plan your trip to San Juan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Juan 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 San Juan when rainfall is around 2.2 in.

Temperature in San Juan by month

Plan your trip to San Juan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Juan, 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 San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated December 22, 2024.
Peruse reviews from past customers who have flown with Delta, Frontier and Spirit Airlines from Chesapeake to San Juan to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.2
Good
10,000 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

6.3
Okay
8,111 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to San Juan. 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 San Juan one-way?

    The cheapest airlines for a one-way flight from Chesapeake to San Juan are American Airlines ($117), Spirit Airlines ($133), and Delta ($152).

  • Can I find deals for flights from Chesapeake to San Juan that include hotel bookings?

    Yes. In addition to deals on Chesapeake to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to San Juan.

  • Can I find deals for business class flights from Chesapeake to San Juan?

    Yes. Cheapflights offers flight deals from Chesapeake to San Juan 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 San Juan?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to San Juan (average of $254). Flying from Chesapeake to San Juan in March is currently the most expensive (average of $380). 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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Top 7 airlines flying from Chesapeake to San Juan

Discover the top 7 airlines that operate flights from Chesapeake to San Juan. 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$142Average$274FlexibilityNo cancel feeOn-time65%
FrontierCheapest$158Average$285FlexibilityNo cancel feeOn-time62%
DeltaCheapest$227Average$392FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$240Average$504FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$247Average$515FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$250Average$437FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$345Average$494FlexibilityNo cancel feeOn-time63%
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