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San Juan

$59+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chesapeake to San Juan are usually found in May or September, booked 50 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Chesapeake to San Juan

Keep the following information in mind while searching for Chesapeake to San Juan flight deals. Data was last updated February 20, 2025.

Round-trip from

$235
(FlightHub)

One-way from

$59
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$387
From Chesapeake to San Juan
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One-way flight from Chesapeake to San Juan
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Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/268:59 pmORF - SJU
2 stops21h 45mSpirit Airlines
Sun 5/410:19 pmSJU - ORF
1 stop13h 03mSpirit Airlines
Deal found 2/19$235
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.
Sat 3/17:16 pmORF - SJU
1 stop6h 38mFrontier
Wed 3/59:30 pmSJU - ORF
1 stop20h 28mFrontier
Deal found 2/19$238
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/296:55 amORF - SJU
1 stop9h 06mDelta
Thu 5/85:35 pmSJU - ORF
1 stop6h 26mDelta
Deal found 2/19$245
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.
Fri 4/258:32 pmORF - SJU
1 stop6h 17mMultiple Airlines
Sun 4/273:52 amSJU - ORF
1 stop7h 30mMultiple Airlines
Deal found 2/19$246
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 10/156:00 amORF - SJU
1 stop7h 45mUnited Airlines
Wed 10/221:05 amSJU - ORF
2 stops8h 30mUnited Airlines
Deal found 2/20$267
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:50 amORF - SJU
2 stops10h 30mAmerican Airlines
Tue 10/1412:00 pmSJU - ORF
2 stops10h 09mAmerican Airlines
Deal found 2/19$375

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 February 20, 2025.

Fly from

Chesapeake

Fly to

San Juan

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 4/26

8:59 pm-6:44 pm

2 stops21h 45m

San Juan Luis Munoz Marin Intl

Thu 5/1

3:52 am-11:22 am

1 stop7h 30m

$235

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 3/1

7:16 pm-2:54 am

1 stop6h 38m

San Juan Luis Munoz Marin Intl

Wed 3/5

9:30 pm-4:58 pm

1 stop20h 28m

$238

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 4/29

5:30 am-11:40 am

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Thu 5/1

7:15 am-6:02 pm

1 stop10h 47m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 4/25

8:32 pm-2:49 am

1 stop6h 17m

San Juan Luis Munoz Marin Intl

Sun 4/27

3:52 am-11:22 am

1 stop7h 30m

$246

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 3/25

6:10 am-3:36 pm

1 stop9h 26m

San Juan Luis Munoz Marin Intl

Tue 3/25

1:05 am-2:17 pm

2 stops13h 12m

$330

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 3/26

7:41 pm-1:52 am

1 stop6h 11m

$59

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 2/27

10:20 am-9:06 pm

1 stop9h 46m

$158

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 3/13

6:32 am-2:40 pm

2 stops8h 08m

$273

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 4/5

6:10 am-8:38 pm

3 stops14h 28m

$536

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 4/5

6:00 am-1:45 pm

3 stops31h 45m

$1,009

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February 14, 2025.

Booking 50 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 $363). 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 February 20, 2025.

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. Sunday at noon 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 February 20, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and United 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.
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,697 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,219 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,765 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Spirit Airlines
6.3
Okay
8,013 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Spirit Airlines ($59), Delta ($158), and American Airlines ($273).

  • 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 $363). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$279FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$161Average$284FlexibilityNo cancel feeOn-time65%
DeltaCheapest$232Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$237Average$499FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$250Average$416FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$257Average$527FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$344Average$507FlexibilityNo cancel feeOn-time63%
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