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Costa Rica

$175+ Cheap flights from Chesapeake, VA to Costa Rica

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
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Cheap flight deals from Chesapeake to Costa Rica

Cheapest flights from Chesapeake to Costa Rica
Explore the most affordable flight options available from Chesapeake to Costa Rica. 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
This KAYAK deal was found by Cheapflights users on 1/27. 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.
Sat 2/2810:04 am
ORF
-
LIR
1 stop27h 51m
JetBlue
Thu 3/51:40 pm
LIR
-
ORF
1 stop18h 34m
JetBlue
Deal found 1/27$444
This United Airlines deal was found by Cheapflights users on 1/27. 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 7/145:15 pm
ORF
-
LIR
2 stops18h 45m
United Airlines
Wed 7/2211:05 am
LIR
-
ORF
1 stop9h 01m
United Airlines
Deal found 1/27$556
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/245:18 pm
ORF
-
LIR
2 stops19h 52m
American Airlines
Tue 3/1012:21 pm
LIR
-
ORF
2 stops18h 03m
American Airlines
Deal found 1/27$561

Find flight deals from Chesapeake to Costa Rica

Keep the following information in mind while searching for Chesapeake to Costa Rica 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 Costa Rica
Search Deals
One-way flight from Chesapeake to Costa Rica
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 Costa Rica 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 Costa Rica that are best for you.

Fly from

Chesapeake

Fly to

Costa Rica

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 22 results
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Best time to book a flight from Chesapeake to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica 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 Costa Rica

What is the cheapest month to book a flight from Chesapeake to Costa Rica?

Currently, August is the cheapest month in which you can book a flight from Chesapeake to Costa Rica (average of $193). Flying from Chesapeake to Costa Rica 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.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Chesapeake to Costa Rica, such as Delta, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,127 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

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

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

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

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

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

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

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

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

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 Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chesapeake to Costa Rica?

    Departing from Chesapeake to Costa Rica will take you 9h 06m. The distance from Chesapeake to Costa Rica is about 1907 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Chesapeake to Costa Rica that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Costa Rica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Costa Rica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Costa Rica.

  • Can I find deals for business class flights from Chesapeake to Costa Rica?

    Yes. Cheapflights offers flight deals from Chesapeake to Costa Rica 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 Costa Rica?

    Currently, August is the cheapest month in which you can book a flight from Chesapeake to Costa Rica (average of $193). Flying from Chesapeake to Costa Rica 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chesapeake to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chesapeake to Costa Rica

Discover the top 6 airlines that operate flights from Chesapeake to Costa Rica. 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$556FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$239Average$417FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$261Average$608FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$261Average$475FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$309Average$571FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$472Average$689FlexibilityNo cancel feeOn-time63%

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