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Costa Rica

$273+ Cheap flights from Chesapeake, VA to Costa Rica

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
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Cheap 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$292
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$609
Provider with most accurate pricing for Norfolk-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-San José Juan Santamaria Intl flights.
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From Chesapeake to Costa Rica
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Highest demand for flights based on searches. 5% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 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
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:00 amORF - LIR
1 stop8h 25mAmerican Airlines
Tue 12/161:25 pmLIR - ORF
1 stop9h 34mAmerican Airlines
Deal found 11/2$453
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:30 amORF - LIR
1 stop9h 10mUnited Airlines
Thu 12/258:35 amLIR - ORF
1 stop13h 10mUnited Airlines
Deal found 11/3$543
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:53 pmORF - LIR
2 stops20h 47mUnited Airlines
Wed 12/248:35 amLIR - ORF
2 stops24h 20mUnited Airlines
Deal found 11/1$608
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:46 amORF - LIR
2 stops9h 27mAmerican Airlines
Sun 11/163:18 pmLIR - ORF
2 stops19h 29mAmerican Airlines
Deal found 11/2$804

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 November 3, 2025.
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

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

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Thu 12/11

5:08 am-12:30 pm

1 stop8h 22m

Liberia

Tue 12/16

1:19 pm-11:15 pm

1 stop8h 56m

$453

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Fri 12/5

7:18 pm-12:29 pm

2 stops18h 11m

Liberia

Tue 12/16

3:20 pm-9:28 am

2 stops17h 08m

$457

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Thu 1/8

5:20 am-1:50 pm

1 stop9h 30m

Liberia

Tue 1/13

2:05 pm-12:16 am

1 stop9h 11m

$461

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Mon 2/2

6:20 am-12:50 pm

1 stop7h 30m

Liberia

Mon 2/9

3:05 pm-12:16 am

1 stop8h 11m

$461

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Mon 1/12

6:10 am-12:12 pm

1 stop7h 02m

Liberia

Tue 1/20

1:46 pm-11:10 pm

1 stop8h 24m

$461

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 14 results
1
2

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 $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 CR?

Find hourly flight availability from Chesapeake to Costa Rica. 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.

Unlike in the morning, when flights are generally more expensive, you can save up to 23% on flights from Chesapeake to Costa Rica by exploring options for tickets at noon.

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 November 3, 2025.
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
8,002 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

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

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

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

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

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

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

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

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

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 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 8h 22m. 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 $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

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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$622FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$259Average$401FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$261Average$601FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$261Average$551FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$321Average$609FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$472Average$819FlexibilityNo cancel feeOn-time63%

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