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San José

$339+ Cheap flights from Chesapeake, VA to San José (SJO)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San José Juan Santamaria Intl are usually found in September or October, booked 61 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from Chesapeake to San José

Keep the following information in mind while searching for Chesapeake to San José flight deals. Data was last updated April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$339
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$661
Provider with most accurate pricing for Norfolk-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-San José Juan Santamaria Intl flights.
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From Chesapeake to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 13% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chesapeake to San José

Cheapest flights from Chesapeake to San José
Explore the most affordable flight options available from Chesapeake to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2025.

This Mytrip deal was found by Cheapflights users on 4/2. 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.
Mon 4/216:13 pmORF - SJO
1 stop19h 05mSpirit Airlines
Sat 4/2612:55 amSJO - ORF
1 stop21h 24mSpirit Airlines
Deal found 4/2$339
This American Airlines deal was found by Cheapflights users on 4/2. 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 10/237:10 pmORF - SJO
2 stops18h 00mAmerican Airlines
Sun 10/262:25 pmSJO - ORF
2 stops17h 58mAmerican Airlines
Deal found 4/2$481
This Copa Airlines deal was found by Cheapflights users on 4/2. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/46:10 amORF - SJO
2 stops12h 13mCopa Airlines
Tue 4/85:52 pmSJO - ORF
2 stops13h 29mCopa Airlines
Deal found 4/2$521
This United deal was found by Cheapflights users on 4/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/85:15 pmORF - SJO
2 stops18h 56mUnited Airlines
Mon 8/185:30 amSJO - ORF
2 stops31h 10mUnited Airlines
Deal found 4/2$527
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Sun 6/229:05 amORF - SJO
2 stops27h 22mMultiple Airlines
Mon 6/307:45 pmSJO - ORF
2 stops20h 11mMultiple Airlines
Deal found 4/2$601
This Avianca deal was found by Cheapflights users on 4/2. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/218:00 pmORF - SJO
2 stops17h 15mAvianca
Sun 5/251:40 amSJO - ORF
2 stops15h 28mAvianca
Deal found 4/2$2,054

Cheapflights Fare Finder

Customize your flight search to find flights from Chesapeake to San José 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 3, 2025.
Use the filters below to find and compare flights from Chesapeake to San José that are best for you.

Fly from

Chesapeake

Fly to

San José

Route

Depart

Return

Price

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 4/21

6:13 pm-11:18 am

1 stop19h 05m

San José Juan Santamaria Intl

Sat 4/26

12:55 am-12:19 am

1 stop21h 24m

$339

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 5/21

6:00 am-12:50 pm

1 stop8h 50m

San José Juan Santamaria Intl

Mon 5/26

6:03 am-11:28 pm

1 stop15h 25m

$488

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 8/8

5:15 pm-10:11 am

2 stops18h 56m

San José Juan Santamaria Intl

Mon 8/18

5:30 am-2:40 pm

2 stops31h 10m

$527

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sun 6/22

9:05 am-10:27 am

2 stops27h 22m

San José Juan Santamaria Intl

Mon 6/30

7:45 pm-5:56 pm

2 stops20h 11m

$601

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 5/21

8:00 pm-11:15 am

2 stops17h 15m

San José Juan Santamaria Intl

Sun 5/25

1:40 am-7:08 pm

2 stops15h 28m

$2,054

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Best time to book a flight from Chesapeake to San José

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

How far ahead should I book a flight from Chesapeake to San José, San José Province?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to San José. Price data was last updated on March 28, 2025.

The best time to book flights from Chesapeake to San José, San José Province is 61 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chesapeake to San José, San José Province?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to San José, San José Province (average of $398). Flying from Chesapeake to San José, San José Province in March is currently the most expensive (average of $555). 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 SJO?

Find hourly flight availability from Chesapeake to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 3, 2025.

When flying from Chesapeake to San José, San José Province, 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 José, San José Province?

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

Travelers seeking maximum savings on their Chesapeake to San José, San José Province flight should consider departing on Wednesday 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 José by month

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

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 in.

Temperature in San José by month

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

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 José. Reviews last updated April 3, 2025.
United Airlines
7.4
Good
8,619 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,619 reviews
United Airlines
7.4
Good
8,619 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,619 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Avianca
6.7
Okay
2,304 reviews
United Airlines
7.4
Good
8,619 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Spirit Airlines
6.3
Okay
7,889 reviews
United Airlines
7.4
Good
8,619 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San José from Chesapeake?

    San José Juan Santamaria Intl (SJO) is the airport you will fly into if you book a flight from Chesapeake to San José. You should not have trouble finding flights to Juan Santamaria Intl from Chesapeake; the airport handles an average of 0 inbound flights from Chesapeake per day. You should also have plenty of airline options to choose from since 6 airlines have flights to the San José airport from Chesapeake. It is only a 8.8 mi journey from Juan Santamaria Intl (SJO) to San José’s city center.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to San José 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 José, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to San José, San José Province (average of $398). Flying from Chesapeake to San José, San José Province in March is currently the most expensive (average of $555). 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

Traveling to a place near Chesapeake?

Book flights to Chesapeake if you plan to visit one of these locations
Manuel Antonio
Heredia
Alajuela
Monteverde
Jacó

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Top 6 airlines flying from Chesapeake to San José

Discover the top 6 airlines that operate flights from Chesapeake to San José. 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$247Average$363FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$336Average$515FlexibilityNo cancel feeOn-time62%
DeltaCheapest$346Average$565FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$360Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$389Average$607FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$480Average$780FlexibilityNo cancel feeOn-time63%

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