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San Juan

$113+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San Juan are usually found in September or May, booked 78 days in advance, depart on a Monday or Tuesday and return on a Monday

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 September 15, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$301
From Chesapeake to San Juan
Search Deals
One-way flight from Chesapeake to San Juan
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Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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 10/288:00 amORF - SJU
1 stop8h 33mDelta
Wed 11/56:43 pmSJU - ORF
1 stop6h 37mDelta
Deal found 9/14$225
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/2512:35 pmORF - SJU
1 stop10h 30mAmerican Airlines
Wed 10/297:45 amSJU - ORF
1 stop7h 31mAmerican Airlines
Deal found 9/14$231
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 10/25:12 pmORF - SJU
1 stop9h 22mFrontier
Mon 10/69:26 pmSJU - ORF
2 stops19h 23mFrontier
Deal found 9/14$234
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/2212:19 pmORF - SJU
1 stop11h 40mAmerican Airlines
Thu 10/235:30 amSJU - ORF
1 stop6h 35mAmerican Airlines
Deal found 9/13$240
This Priceline deal was found by Cheapflights users on 9/13. 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.
Sun 9/285:47 pmORF - SJU
1 stop8h 47mFrontier
Wed 10/13:39 amSJU - ORF
1 stop12h 33mFrontier
Deal found 9/13$242
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 10/315:24 amORF - SJU
1 stop6h 12mDelta
Sat 11/11:06 pmSJU - ORF
1 stop9h 59mDelta
Deal found 9/13$245
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 11/156:00 amORF - SJU
2 stops14h 00mUnited Airlines
Wed 11/192:05 amSJU - ORF
2 stops13h 29mUnited Airlines
Deal found 9/13$253
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 11/156:00 amORF - SJU
2 stops14h 00mUnited Airlines
Tue 11/188:30 amSJU - ORF
1 stop6h 28mUnited Airlines
Deal found 9/13$263
This Frontier deal was found by Cheapflights users on 9/13. 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.
Thu 10/25:12 pmORF - SJU
1 stop9h 22mFrontier
Sun 10/59:07 amSJU - ORF
1 stop7h 50mFrontier
Deal found 9/13$264
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 12/47:29 pmORF - SJU
1 stop15h 30mAmerican Airlines
Sat 12/136:25 amSJU - ORF
1 stop13h 28mAmerican Airlines
Deal found 9/14$265
This Priceline deal was found by Cheapflights users on 9/13. 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.
Fri 10/315:38 pmORF - SJU
1 stop8h 06mMultiple Airlines
Sat 11/13:04 amSJU - ORF
1 stop10h 12mMultiple Airlines
Deal found 9/13$274

Cheapflights Fare Finder

 
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 September 15, 2025.
Use the filters below to find and compare flights from Chesapeake to San Juan that are best for you.

Fly from

Chesapeake

Fly to

San Juan

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 10/29

1:36 pm-9:59 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Tue 11/4

7:15 am-12:31 pm

1 stop6h 16m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 10/28

6:00 am-1:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:05 am-10:49 am

1 stop9h 44m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 10/28

2:55 pm-11:50 pm

2 stops8h 55m

San Juan Luis Munoz Marin Intl

Wed 11/5

2:05 pm-10:00 pm

2 stops8h 55m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 10/28

6:07 am-6:25 pm

2 stops12h 18m

San Juan Luis Munoz Marin Intl

Wed 11/5

8:20 am-1:42 pm

1 stop6h 22m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 10/29

12:22 pm-9:59 pm

1 stop9h 37m

San Juan Luis Munoz Marin Intl

Sat 11/1

1:06 pm-11:05 pm

1 stop9h 59m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 10/31

5:24 am-4:33 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

Tue 11/4

7:15 am-3:18 pm

1 stop9h 03m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 10/30

5:24 am-4:33 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

Wed 11/5

2:06 pm-11:05 pm

1 stop9h 59m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 10/28

8:00 am-4:33 pm

1 stop8h 33m

San Juan Luis Munoz Marin Intl

Wed 11/5

6:43 pm-12:20 am

1 stop6h 37m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 10/19

6:10 am-12:10 pm

1 stop6h 00m

San Juan Luis Munoz Marin Intl

Wed 10/22

6:10 am-3:55 pm

1 stop9h 45m

$275

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 11/3

5:45 am-2:12 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-3:18 pm

1 stop9h 03m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 21 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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to San Juan

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 September 12, 2025.

Booking 78 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 June is currently the most expensive (average of $339). 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 September 15, 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 Thursday 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.

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 September 15, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chesapeake to San Juan by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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 San Juan. 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 San Juan?

    Departing from Chesapeake to San Juan will take you 7h 40m. Chesapeake and San Juan are separated by a distance of 1416 mi. This flight may include one or multiple stops.

  • 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 June is currently the most expensive (average of $339). 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 San Juan

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 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$164Average$293FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$421FlexibilityNo cancel feeOn-time62%
DeltaCheapest$234Average$382FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$498FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$254Average$540FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$508FlexibilityNo cancel feeOn-time63%

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