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$307+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Chesapeake to San José Juan Santamaria Intl are usually found in September or October, booked 45 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from Chesapeake to San José

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$307
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$538
From Chesapeake to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 14% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/26:12 pmORF - SJO
1 stop18h 12mMultiple Airlines
Mon 3/1712:26 pmSJO - ORF
1 stop20h 04mMultiple Airlines
Deal found 1/21$307
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/266:09 amORF - SJO
1 stop15h 56mAmerican Airlines
Wed 3/53:10 pmSJO - ORF
1 stop16h 24mAmerican Airlines
Deal found 1/21$332
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/194:29 pmORF - SJO
2 stops19h 55mSpirit Airlines
Mon 3/312:29 pmSJO - ORF
1 stop9h 52mSpirit Airlines
Deal found 1/20$335
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 2/2210:40 amORF - SJO
2 stops10h 59mUnited Airlines
Thu 2/278:45 amSJO - ORF
2 stops28h 31mUnited Airlines
Deal found 1/20$536
This Copa Airlines deal was found by Cheapflights users on 1/20. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/217:50 pmORF - SJO
2 stops24h 02mCopa Airlines
Tue 1/2810:56 amSJO - ORF
2 stops21h 42mCopa Airlines
Deal found 1/20$556
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/293:40 pmORF - SJO
2 stops22h 30mSouthwest
Sat 4/51:35 pmSJO - ORF
2 stops18h 55mSouthwest
Deal found 1/20$655

Find flights from Chesapeake to San José within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sun 3/2

6:12 pm-11:24 am

1 stop18h 12m

San José Juan Santamaria Intl

Mon 3/17

12:26 pm-10:30 am

1 stop20h 04m

$307

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 2/26

6:09 am-9:05 pm

1 stop15h 56m

San José Juan Santamaria Intl

Wed 3/5

3:10 pm-8:34 am

1 stop16h 24m

$332

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 2/19

4:29 pm-11:24 am

2 stops19h 55m

San José Juan Santamaria Intl

Mon 3/3

12:29 pm-11:21 pm

1 stop9h 52m

$335

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sat 2/22

10:40 am-8:39 pm

2 stops10h 59m

San José Juan Santamaria Intl

Thu 2/27

8:45 am-2:16 pm

2 stops28h 31m

$536

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sat 3/29

3:40 pm-12:10 pm

2 stops22h 30m

San José Juan Santamaria Intl

Sat 4/5

1:35 pm-10:30 am

2 stops18h 55m

$655

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Tue 2/18

6:00 am-6:55 pm

2 stops37h 55m

San José Juan Santamaria Intl

Tue 2/25

7:50 pm-9:40 am

2 stops12h 50m

$896

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sat 3/1

6:00 am-10:05 pm

2 stops17h 05m

San José Juan Santamaria Intl

Fri 3/7

4:09 am-7:27 pm

2 stops14h 18m

$1,914

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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.

Travel insights for flights from Chesapeake to San José

Get recent, data-driven insights about flights from Chesapeake to San José including ideal travel times, pricing trends, and more.

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 January 17, 2025.

The best time to book flights from Chesapeake to San José, San José Province is 45 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 January 21, 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 January 21, 2025.
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Avianca
6.9
Okay
2,579 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 5 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
Jacó
Monteverde
Alajuela

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Top 5 airlines flying from Chesapeake to San José

Discover the top 5 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$224Average$333FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$322Average$506FlexibilityNo cancel feeOn-time62%
DeltaCheapest$346Average$571FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$371Average$589FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$413Average$650FlexibilityNo cancel feeOn-time69%
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