HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Juan

$128+ 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 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
Sun 5/4
Sun 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to San Juan with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: 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 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 April 29, 2025.

Round-trip from

$245
(Delta)

One-way from

$128
(Delta)

Popular in

December

Cheapest in

July

Average price

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

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 April 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.
Tue 9/167:00 amORF - SJU
1 stop9h 18mDelta
Tue 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.
Wed 5/2812:13 pmORF - SJU
1 stop12h 41mSpirit Airlines
Mon 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.
Sat 9/208:32 amORF - SJU
2 stops11h 38mAmerican Airlines
Sat 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.
Thu 6/124:11 pmORF - SJU
1 stop27h 08mMultiple Airlines
Sun 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.
Thu 5/223:28 pmORF - SJU
1 stop8h 53mFrontier
Sun 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.
Tue 9/166:30 amORF - SJU
1 stop8h 14mUnited Airlines
Mon 10/61:05 amSJU - ORF
2 stops13h 35mUnited Airlines
Deal found 4/29$335
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.
Tue 7/14:00 pmORF - SJU
1 stop7h 25mSouthwest
Sat 7/55:00 amSJU - ORF
1 stop11h 00mSouthwest
Deal found 4/28$454

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 April 29, 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 5/28

12:13 pm-12:54 am

1 stop12h 41m

San Juan Luis Munoz Marin Intl

Mon 6/2

8:12 pm-10:29 am

2 stops14h 17m

$251

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 5/29

4:21 pm-11:42 pm

1 stop7h 21m

San Juan Luis Munoz Marin Intl

Thu 6/5

1:12 pm-11:02 pm

1 stop9h 50m

$255

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 6/2

10:26 am-9:17 pm

2 stops34h 51m

San Juan Luis Munoz Marin Intl

Fri 6/6

8:12 pm-4:35 pm

1 stop20h 23m

$258

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 5/21

8:24 pm-1:20 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Wed 5/28

11:50 am-11:28 pm

1 stop11h 38m

$303

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 5/22

3:28 pm-2:32 am

1 stop11h 04m

San Juan Luis Munoz Marin Intl

Sun 5/25

6:00 am-2:33 pm

1 stop8h 33m

$318

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 5/9

6:25 am-5:45 pm

2 stops11h 20m

San Juan Luis Munoz Marin Intl

Mon 5/12

7:40 am-6:45 pm

2 stops11h 05m

$497

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 5/29

6:15 am-1:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Wed 6/4

1:05 am-9:41 am

2 stops8h 36m

$505

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 7/12

6:50 pm-1:31 am

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Thu 7/17

7:20 am-5:54 pm

1 stop10h 34m

$530

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 5/26

6:15 am-1:45 pm

1 stop7h 30m

$128

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 6/24

7:32 pm-7:19 pm

1 stop23h 47m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 14 results
1
2

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 April 25, 2025.

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 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 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 April 29, 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 April 29, 2025.
Peruse reviews from past customers who have flown with Southwest, 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.
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

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

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

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

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

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

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

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

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

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

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Boarding

8.2

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 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 Delta ($128), Frontier ($149), and American Airlines ($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 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to San Juan

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
Richmond to Luis Munoz Marin Intl flights
Norfolk to Luis Munoz Marin Intl flights
Greensboro to Luis Munoz Marin Intl flights
Dulles Intl to Ponce flights
Blountville to Luis Munoz Marin Intl flights
Reagan-National to Aguadilla flights
Raleigh to Ponce flights
Dulles Intl to Aguadilla flights
Raleigh to Aguadilla flights
Roanoke to Luis Munoz Marin Intl flights
Charlottesville to Luis Munoz Marin Intl flights
Richmond to Aguadilla flights
Newport News to Luis Munoz Marin Intl flights
Richmond to Ponce flights
Salisbury to Luis Munoz Marin Intl flights
Dulles Intl to Culebra flights
Dulles Intl to Vieques flights
Raleigh to Culebra flights
Norfolk to Vieques flights
Reagan-National to Vieques flights
Reagan-National to Culebra flights
Reagan-National to Mayagüez flights
Staunton to Luis Munoz Marin Intl flights
Richmond to Vieques flights
Richmond to Culebra flights
Reagan-National to Ponce flights
Newport News to Aguadilla flights
Greensboro to Aguadilla flights
Norfolk to Aguadilla flights

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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$163Average$283FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$224Average$494FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$375FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$562FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$255Average$412FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$345Average$519FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.