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San José

$144+ Cheap flights from Chesapeake, VA to San José (SJO)

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 May, booked 62 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 July 31, 2025.

Round-trip from

$283
(FlightHub)

One-way from

$144
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$579
From Chesapeake to San José Juan Santamaria Intl
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One-way flight from Chesapeake to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 10% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 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 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 July 31, 2025.

This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/185:30 amORF - SJO
1 stop7h 42mSpirit Airlines
Tue 8/2612:18 pmSJO - ORF
1 stop8h 16mSpirit Airlines
Deal found 7/30$283
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Fri 9/195:20 amORF - SJO
1 stop7h 54mMultiple Airlines
Mon 9/227:30 amSJO - ORF
1 stop7h 13mMultiple Airlines
Deal found 7/31$316
This Delta deal was found by Cheapflights users on 7/31. 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 10/215:24 amORF - SJO
1 stop8h 32mDelta
Tue 10/281:21 pmSJO - ORF
1 stop8h 59mDelta
Deal found 7/31$460

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 July 31, 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 8/18

5:30 am-11:12 am

1 stop7h 42m

San José Juan Santamaria Intl

Tue 8/26

12:18 pm-10:34 pm

1 stop8h 16m

$283

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 9/19

5:20 am-11:14 am

1 stop7h 54m

San José Juan Santamaria Intl

Mon 9/22

7:30 am-4:43 pm

1 stop7h 13m

$316

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Tue 10/21

5:24 am-11:56 am

1 stop8h 32m

San José Juan Santamaria Intl

Thu 10/30

1:21 pm-12:20 am

1 stop8h 59m

$460

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sun 1/11

8:00 pm-4:48 pm

2 stops21h 48m

San José Juan Santamaria Intl

Sun 1/18

5:51 pm-9:35 am

2 stops14h 44m

$462

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 8/14

7:39 pm-10:32 am

1 stop16h 53m

$144

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sat 8/16

5:20 pm-10:32 am

1 stop19h 12m

$145

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 10/1

5:30 am-12:08 pm

1 stop8h 38m

$150

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 8/11

8:10 pm-7:34 am

2 stops13h 24m

$219

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sun 8/10

5:13 pm-1:40 pm

2 stops22h 27m

$269

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 8/13

6:10 am-11:15 am

3 stops31h 05m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 11 results
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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 July 25, 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 July 31, 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.

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 July 31, 2025.
Get a feel of what it's like to fly with Delta, Copa Airlines, and United Airlines from Chesapeake to San José by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,493 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Avianca
6.7
Okay
2,388 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Chesapeake to San José, San José Province one-way?

    One-way options have recently been found by users for as low as $145 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $150 and Copa Airlines from $219 one-way.

  • 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 San José?

Book flights to San José if you plan to visit one of these locations
Heredia
Manuel Antonio
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$259Average$389FlexibilityNo cancel feeOn-time65%
DeltaCheapest$333Average$543FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$336Average$466FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$359Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$389Average$623FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$480Average$732FlexibilityNo cancel feeOn-time63%

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