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San José

$195+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 64 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 September 17, 2025.

Round-trip from

$195
(Expedia)

Popular in

December

Cheapest in

September

Average price

$358
From Chesapeake to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 September 17, 2025.

This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:20 amORF - SJO
1 stop7h 54mSpirit Airlines
Thu 10/212:19 pmSJO - ORF
1 stop8h 29mSpirit Airlines
Deal found 9/15$195
This Travelocity deal was found by Cheapflights users on 9/16. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:24 amORF - SJO
1 stop8h 06mSpirit Airlines
Thu 10/2312:35 pmSJO - ORF
1 stop8h 11mSpirit Airlines
Deal found 9/16$259
This Mytrip deal was found by Cheapflights users on 9/16. 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 11/108:01 amORF - SJO
1 stop8h 15mMultiple Airlines
Fri 11/147:30 amSJO - ORF
1 stop15h 37mMultiple Airlines
Deal found 9/16$265
This CheapOair deal was found by Cheapflights users on 9/15. 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 - SJO
1 stop8h 06mSpirit Airlines
Sun 10/2612:35 pmSJO - ORF
1 stop8h 11mSpirit Airlines
Deal found 9/15$283
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Mon 11/35:24 amORF - SJO
1 stop8h 06mMultiple Airlines
Sat 11/151:19 pmSJO - ORF
2 stops20h 30mMultiple Airlines
Deal found 9/16$321

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 September 17, 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 11/3

5:24 am-12:30 pm

1 stop8h 06m

San José Juan Santamaria Intl

Sat 11/15

1:19 pm-11:40 pm

1 stop9h 21m

$259

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/10

8:01 am-3:16 pm

1 stop8h 15m

San José Juan Santamaria Intl

Fri 11/14

7:30 am-12:07 am

1 stop15h 37m

$265

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 9/29

5:38 pm-11:14 am

2 stops19h 36m

San José Juan Santamaria Intl

Thu 10/2

12:19 pm-4:43 pm

3 stops26h 24m

$333

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/3

4:57 pm-12:30 pm

2 stops20h 33m

San José Juan Santamaria Intl

Fri 11/7

12:22 pm-12:07 am

1 stop10h 45m

$349

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/3

5:24 am-12:30 pm

1 stop8h 06m

San José Juan Santamaria Intl

Fri 11/14

4:08 am-11:40 pm

2 stops18h 32m

$370

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 10/1

10:33 am-11:35 pm

2 stops15h 02m

San José Juan Santamaria Intl

Tue 10/7

4:20 pm-9:37 am

2 stops15h 17m

$378

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 12/15

12:35 pm-8:52 am

1 stop21h 17m

San José Juan Santamaria Intl

Mon 12/29

5:31 pm-11:49 am

1 stop17h 18m

$421

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/10

8:01 am-12:14 pm

3 stops29h 13m

San José Juan Santamaria Intl

Fri 11/14

12:22 pm-11:40 pm

3 stops34h 18m

$456

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 1/30

7:45 pm-8:40 am

2 stops13h 55m

San José Juan Santamaria Intl

Mon 2/9

4:15 pm-9:52 am

2 stops16h 37m

$477

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 12/25

7:00 am-7:10 am

2 stops25h 10m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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 September 12, 2025.

The best time to book flights from Chesapeake to San José, San José Province is 57 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 $554). 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 September 17, 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 September 17, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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.

  • How long is the flight from Chesapeake to San José, San José Province?

    Departing from Chesapeake to San José, San José Province will take you 8h 06m. Airlines will cover a distance of 1923 mi.

  • 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 $554). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$259Average$396FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$320Average$476FlexibilityNo cancel feeOn-time62%
DeltaCheapest$321Average$560FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$389Average$629FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$390Average$621FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$480Average$780FlexibilityNo cancel feeOn-time63%

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