HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José

$273+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 March, 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$277
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$609
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
Highest demand for flights based on searches. 5% potential increase in price ($32 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 November 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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:03 pmORF - SJO
1 stop15h 36mMultiple Airlines
Wed 11/1212:34 pmSJO - ORF
1 stop23h 41mMultiple Airlines
Deal found 11/2$273
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 11/139:03 pmORF - SJO
1 stop15h 36mSpirit Airlines
Sun 11/1612:34 pmSJO - ORF
1 stop22h 50mSpirit Airlines
Deal found 11/3$292
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/232:10 pmORF - SJO
1 stop21h 09mMultiple Airlines
Fri 12/51:31 pmSJO - ORF
1 stop28h 45mMultiple Airlines
Deal found 11/1$305
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/38:02 pmORF - SJO
1 stop17h 23mSpirit Airlines
Wed 12/101:31 pmSJO - ORF
1 stop28h 45mSpirit Airlines
Deal found 11/3$307
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 11/139:03 pmORF - SJO
1 stop15h 36mMultiple Airlines
Sun 11/161:30 pmSJO - ORF
2 stops20h 04mMultiple Airlines
Deal found 11/1$323
This CheapOair deal was found by Cheapflights users on 11/1. 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.
Fri 12/512:35 pmORF - SJO
1 stop21h 17mJetBlue
Sun 12/710:00 amSJO - ORF
1 stop24h 49mJetBlue
Deal found 11/1$326
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:02 pmORF - SJO
1 stop17h 23mSpirit Airlines
Sat 12/61:31 pmSJO - ORF
1 stop28h 45mSpirit Airlines
Deal found 11/2$327
This KAYAK deal was found by Cheapflights users on 11/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:26 pmORF - SJO
1 stop13h 53mSpirit Airlines
Mon 12/81:31 pmSJO - ORF
1 stop28h 45mSpirit Airlines
Deal found 11/1$331

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 November 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

Thu 11/13

9:03 pm-11:39 am

1 stop15h 36m

San José Juan Santamaria Intl

Sun 11/16

1:30 pm-12:24 pm

2 stops21h 54m

$325

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 12/3

8:02 pm-12:25 pm

1 stop17h 23m

San José Juan Santamaria Intl

Wed 12/10

1:31 pm-10:58 pm

2 stops32h 27m

$337

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 1/2

3:01 pm-12:25 pm

1 stop22h 24m

San José Juan Santamaria Intl

Fri 1/9

1:16 am-5:02 pm

1 stop14h 46m

$339

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 12/3

9:26 pm-11:42 am

1 stop15h 16m

San José Juan Santamaria Intl

Wed 12/10

12:39 pm-7:16 pm

3 stops29h 37m

$394

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sat 1/3

7:40 pm-12:25 pm

2 stops41h 45m

San José Juan Santamaria Intl

Sat 1/10

1:19 pm-7:14 pm

1 stop28h 55m

$397

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 1/30

7:45 am-10:15 pm

1 stop15h 30m

San José Juan Santamaria Intl

Mon 2/9

7:00 am-8:30 pm

1 stop12h 30m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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?

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 October 31, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to San José, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, September is the cheapest month in which you can book a flight from Chesapeake to San José (average of $224). Flying from Chesapeake to San José in June is currently the most expensive (average of $437). 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 November 3, 2025.

It’s typically best to fly out from Chesapeake to San José in the evening. Doing so could potentially save you 45% on the flight price compared to flying in the afternoon, which is usually more expensive.

How much does it cost to fly round-trip from Chesapeake to San José?

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 November 3, 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
7.9
Good
8,002 reviews

Crew

8.5

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,002 reviews
Delta
7.9
Good
8,002 reviews

Crew

8.5

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
8,002 reviews

Crew

8.5

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,038 reviews
Delta
7.9
Good
8,002 reviews

Crew

8.5

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,115 reviews
Delta
7.9
Good
8,002 reviews

Crew

8.5

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    A quick flight from Chesapeake to San José can take about 15h 36m. Spirit Airlines provides one of the quickest options available for as low as $325. 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?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to San José (average of $224). Flying from Chesapeake to San José in June is currently the most expensive (average of $437). 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
Dominical

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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$585FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$259Average$400FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$261Average$560FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$273Average$466FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$321Average$616FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$472Average$884FlexibilityNo 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.