HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José

$175+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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.

Cheap 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 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/28. 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.
Sat 2/288:44 pm
ORF
-
SJO
1 stop16h 38m
Spirit Airlines
Wed 3/412:35 pm
SJO
-
ORF
1 stop8h 15m
Spirit Airlines
Deal found 1/28$221
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Tue 2/247:31 pm
ORF
-
SJO
1 stop17h 51m
Spirit Airlines
Mon 3/21:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$265
This CheapOair deal was found by Cheapflights users on 1/28. 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 2/267:31 pm
ORF
-
SJO
2 stops17h 09m
Spirit Airlines
Wed 3/41:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$266
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 2/247:31 pm
ORF
-
SJO
1 stop17h 51m
Spirit Airlines
Wed 3/41:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$267
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 2/247:31 pm
ORF
-
SJO
1 stop17h 51m
Spirit Airlines
Mon 3/912:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$274
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/237:31 pm
ORF
-
SJO
1 stop17h 51m
Spirit Airlines
Wed 3/41:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$275
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/237:31 pm
ORF
-
SJO
1 stop17h 51m
Spirit Airlines
Mon 3/912:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$282
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/227:31 pm
ORF
-
SJO
2 stops17h 09m
Spirit Airlines
Wed 3/41:31 pm
SJO
-
ORF
1 stop27h 55m
Spirit Airlines
Deal found 1/28$283
This CheapOair deal was found by Cheapflights users on 1/28. 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 2/267:31 pm
ORF
-
SJO
2 stops17h 09m
Spirit Airlines
Fri 3/612:35 pm
SJO
-
ORF
1 stop8h 15m
Spirit Airlines
Deal found 1/28$284

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$221
(Mytrip)

One-way from

$175
(FlightHub)

Popular in

June

Cheapest in

September

Average price

$613
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. 3% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Tue 2/24

7:31 pm-12:22 pm

1 stop17h 51m

San José Juan Santamaria Intl

Mon 3/2

1:31 pm-6:26 pm

1 stop27h 55m

$265

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 2/23

7:31 pm-12:22 pm

1 stop17h 51m

San José Juan Santamaria Intl

Mon 3/9

12:31 pm-6:26 pm

1 stop27h 55m

$282

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 2/26

7:31 pm-11:40 am

2 stops17h 09m

San José Juan Santamaria Intl

Thu 3/5

12:35 pm-9:50 pm

1 stop8h 15m

$284

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 3/9

7:31 pm-11:22 am

1 stop17h 51m

San José Juan Santamaria Intl

Fri 3/13

11:38 am-10:32 pm

1 stop8h 54m

$291

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 2/27

7:31 pm-12:22 pm

1 stop17h 51m

San José Juan Santamaria Intl

Wed 3/4

1:31 pm-6:26 pm

1 stop27h 55m

$295

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Fri 2/27

6:45 am-11:40 am

1 stop29h 55m

San José Juan Santamaria Intl

Thu 3/5

12:35 pm-9:50 pm

1 stop8h 15m

$314

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 3/9

7:31 pm-10:40 am

2 stops17h 09m

San José Juan Santamaria Intl

Sat 3/14

11:38 am-10:32 pm

1 stop8h 54m

$337

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 3/5

7:31 pm-11:40 am

2 stops17h 09m

San José Juan Santamaria Intl

Thu 3/12

11:38 am-10:32 pm

1 stop8h 54m

$339

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Sat 3/28

6:45 am-10:42 am

1 stop5h 57m

San José Juan Santamaria Intl

Sat 4/4

11:38 am-10:32 pm

1 stop8h 54m

$339

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Thu 3/19

6:45 am-10:42 am

1 stop5h 57m

San José Juan Santamaria Intl

Sat 4/4

10:06 am-8:09 am

1 stop20h 03m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 13 results
1
2

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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chesapeake to San José, you should look to book at least 22 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 $238). Flying from Chesapeake to San José in June is currently the most expensive (average of $358). 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.

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 January 29, 2026.
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
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.9

Food

7.2

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
8,127 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.9

Food

7.2

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
9,215 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.9

Food

7.2

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
11,206 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.9

Food

7.2

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
8,394 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.9

Food

7.2

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 17h 51m. Spirit Airlines provides one of the quickest options available for as low as $265. 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 $238). Flying from Chesapeake to San José in June is currently the most expensive (average of $358). 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
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$162Average$509FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$239Average$417FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$261Average$572FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$261Average$420FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$309Average$561FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$472Average$689FlexibilityNo 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.