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$172+ 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 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
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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 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.
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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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One-way flight from Chesapeake to Costa Rica
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Highest demand for flights based on searches. 5% potential increase in price ($33 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 April 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 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 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.
Tue 7/16:26 amORF - LIR
1 stop8h 49mAmerican Airlines
Thu 7/312:18 pmLIR - ORF
1 stop7h 01mAmerican Airlines
Deal found 4/23$497
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 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 7/15:35 pmORF - LIR
2 stops18h 25mUnited Airlines
Thu 7/313:25 pmLIR - ORF
3 stops30h 11mUnited Airlines
Deal found 4/23$591
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 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 April 24, 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

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

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Tue 7/1

6:26 am-1:15 pm

1 stop8h 49m

Liberia

Thu 7/31

2:18 pm-11:19 pm

1 stop7h 01m

$497

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

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Tue 7/1

5:35 pm-10:00 am

2 stops18h 25m

Liberia

Thu 7/31

3:25 pm-11:36 pm

3 stops30h 11m

$591

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 14 results
1
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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, September is the cheapest month in which you can book a flight from Chesapeake to Costa Rica (average of $398). Flying from Chesapeake to Costa Rica 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 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 April 24, 2025.

When flying from Chesapeake to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Costa Rica 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 Costa Rica when rainfall is around 0.0 in.

Temperature in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Costa Rica, 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 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 April 24, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chesapeake to Costa Rica. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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

  • What are the cheapest airlines to fly from Chesapeake to Costa Rica one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $172. American Airlines flights start at $327 while deals on United Airlines start at $797 one-way.

  • 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, September is the cheapest month in which you can book a flight from Chesapeake to Costa Rica (average of $398). Flying from Chesapeake to Costa Rica 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$247Average$363FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$332Average$502FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$346Average$634FlexibilityNo cancel feeOn-time71%
DeltaCheapest$346Average$652FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$389Average$644FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$480Average$780FlexibilityNo cancel feeOn-time63%

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