HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José

$172+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to San José 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 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 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$352
(Kiwi.com)

One-way from

$172
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$670
Provider with most accurate pricing for Norfolk-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-San José Juan Santamaria Intl flights.
Search Deals
From Chesapeake to San José Juan Santamaria Intl
Search Deals
One-way flight from Chesapeake to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 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 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 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/712:13 pmORF - SJO
1 stop24h 14mMultiple Airlines
Wed 5/1411:32 amSJO - ORF
1 stop20h 59mMultiple Airlines
Deal found 4/23$352
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Wed 5/712:13 pmORF - SJO
1 stop24h 14mSpirit Airlines
Wed 5/1412:28 pmSJO - ORF
2 stops20h 01mSpirit Airlines
Deal found 4/23$385
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/78:28 amORF - SJO
2 stops12h 07mAmerican Airlines
Wed 5/1412:27 pmSJO - ORF
2 stops9h 28mAmerican Airlines
Deal found 4/23$391
This Delta deal was found by Cheapflights users on 4/23. 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 7/225:30 amORF - SJO
1 stop8h 18mDelta
Sat 8/21:08 pmSJO - ORF
1 stop8h 58mDelta
Deal found 4/23$430
This United Airlines deal was found by Cheapflights users on 4/23. 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 10/216:00 amORF - SJO
1 stop7h 38mUnited Airlines
Sun 10/2610:28 pmSJO - ORF
2 stops13h 48mUnited Airlines
Deal found 4/23$459
This Southwest deal was found by Cheapflights users on 4/23. 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 7/225:25 amORF - SJO
2 stops16h 15mSouthwest
Fri 8/18:45 amSJO - ORF
2 stops12h 50mSouthwest
Deal found 4/23$582
This Ovago deal was found by Cheapflights users on 4/23. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:27 amORF - SJO
2 stops19h 03mAvianca
Tue 5/131:55 amSJO - ORF
2 stops15h 07mAvianca
Deal found 4/23$993

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 24, 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

Wed 5/7

12:13 pm-10:27 am

1 stop24h 14m

San José Juan Santamaria Intl

Wed 5/14

11:32 am-10:31 am

1 stop20h 59m

$352

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 5/7

12:13 pm-10:27 am

1 stop24h 14m

San José Juan Santamaria Intl

Wed 5/14

12:28 pm-10:29 am

2 stops20h 01m

$385

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 5/7

8:28 am-6:35 pm

2 stops12h 07m

San José Juan Santamaria Intl

Wed 5/14

12:27 pm-11:55 pm

2 stops9h 28m

$391

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Tue 7/22

5:30 am-11:48 am

1 stop8h 18m

San José Juan Santamaria Intl

Sat 8/2

1:08 pm-12:06 am

1 stop8h 58m

$430

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Tue 10/21

6:00 am-11:38 am

1 stop7h 38m

San José Juan Santamaria Intl

Sun 10/26

10:28 pm-2:16 pm

2 stops13h 48m

$459

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Tue 7/22

5:25 am-7:40 pm

2 stops16h 15m

San José Juan Santamaria Intl

Fri 8/1

8:45 am-11:35 pm

2 stops12h 50m

$582

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 5/7

6:27 am-11:30 pm

2 stops19h 03m

San José Juan Santamaria Intl

Tue 5/13

1:55 am-7:02 pm

2 stops15h 07m

$993

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 6/19

4:11 pm-10:37 am

2 stops20h 26m

$172

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 6/19

10:43 am-10:37 am

1 stop25h 54m

$178

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 6/19

6:00 am-10:39 pm

3 stops18h 39m

$797

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 April 18, 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 24, 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 24, 2025.
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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!
Avianca
6.7
Okay
2,319 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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 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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó

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.

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 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$247Average$363FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$332Average$502FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$346Average$636FlexibilityNo cancel feeOn-time71%
DeltaCheapest$346Average$552FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$389Average$607FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$480Average$780FlexibilityNo 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.