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San Juan

$98+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San Juan are usually found in September or October, booked 67 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 July 30, 2025.

Round-trip from

$204
(CheapOair)

One-way from

$98
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$470
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. 6% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:24 amORF - SJU
1 stop5h 47mMultiple Airlines
Sun 10/269:07 amSJU - ORF
1 stop6h 15mMultiple Airlines
Deal found 7/28$204
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 9/167:10 amORF - SJU
1 stop9h 07mDelta
Tue 9/237:00 amSJU - ORF
1 stop10h 39mDelta
Deal found 7/28$205
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 9/210:30 amORF - SJU
2 stops13h 27mUnited Airlines
Tue 10/71:05 amSJU - ORF
2 stops8h 32mUnited Airlines
Deal found 7/30$216
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/115:12 pmORF - SJU
1 stop6h 47mFrontier
Thu 9/259:07 amSJU - ORF
1 stop7h 05mFrontier
Deal found 7/27$226
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Mon 8/255:20 pmORF - SJU
1 stop6h 37mSpirit Airlines
Thu 9/411:59 amSJU - ORF
1 stop10h 49mSpirit Airlines
Deal found 7/29$228
This Southwest deal was found by Cheapflights users on 7/30. 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.
Wed 9/172:20 pmORF - SJU
1 stop8h 10mSouthwest
Sun 9/215:05 amSJU - ORF
1 stop9h 20mSouthwest
Deal found 7/30$245
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/175:30 amORF - SJU
2 stops10h 22mAmerican Airlines
Tue 9/3012:01 pmSJU - ORF
2 stops10h 36mAmerican Airlines
Deal found 7/30$284

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 July 30, 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

Thu 10/23

5:24 am-11:11 am

1 stop5h 47m

San Juan Luis Munoz Marin Intl

Sun 10/26

9:07 am-3:22 pm

1 stop6h 15m

$204

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 9/16

7:10 am-4:17 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Tue 9/23

7:00 am-5:39 pm

1 stop10h 39m

$205

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 9/2

10:30 am-11:57 pm

2 stops13h 27m

San Juan Luis Munoz Marin Intl

Tue 10/7

1:05 am-9:37 am

2 stops8h 32m

$216

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 9/11

5:12 pm-11:59 pm

1 stop6h 47m

San Juan Luis Munoz Marin Intl

Thu 9/25

9:07 am-4:12 pm

1 stop7h 05m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 8/25

5:20 pm-11:57 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Thu 9/4

11:59 am-10:48 pm

1 stop10h 49m

$228

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 9/17

2:20 pm-10:30 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Sun 9/21

5:05 am-2:25 pm

1 stop9h 20m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 9/17

5:30 am-3:52 pm

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Tue 9/30

12:01 pm-10:37 pm

2 stops10h 36m

$284

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 8/18

5:30 am-9:48 pm

1 stop16h 18m

$98

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 8/7

7:39 pm-2:39 am

1 stop7h 00m

$118

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 8/18

9:50 am-6:15 pm

2 stops8h 25m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 14 results
1
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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 July 25, 2025.

Booking 67 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 July 30, 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 July 30, 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
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 ($98), Frontier ($118), and United Airlines ($148).

  • 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

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$292FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$407FlexibilityNo cancel feeOn-time62%
DeltaCheapest$234Average$381FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$253Average$505FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$254Average$547FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$290Average$514FlexibilityNo cancel feeOn-time63%

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