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Costa Rica

$195+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJO
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$195
(Expedia)

Popular in

December

Cheapest in

September

Average price

$358
From Chesapeake to Costa Rica
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 17, 2025.

This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:20 amORF - SJO
1 stop7h 54mSpirit Airlines
Thu 10/212:19 pmSJO - ORF
1 stop8h 29mSpirit Airlines
Deal found 9/15$195
This Travelocity deal was found by Cheapflights users on 9/16. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:24 amORF - SJO
1 stop8h 06mSpirit Airlines
Thu 10/2312:35 pmSJO - ORF
1 stop8h 11mSpirit Airlines
Deal found 9/16$259
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Mon 11/108:01 amORF - SJO
1 stop8h 15mMultiple Airlines
Fri 11/147:30 amSJO - ORF
1 stop15h 37mMultiple Airlines
Deal found 9/16$265
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/235:24 amORF - SJO
1 stop8h 06mSpirit Airlines
Sun 10/2612:35 pmSJO - ORF
1 stop8h 11mSpirit Airlines
Deal found 9/17$274
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/35:24 amORF - SJO
1 stop8h 06mMultiple Airlines
Sat 11/151:19 pmSJO - ORF
2 stops20h 30mMultiple Airlines
Deal found 9/16$321
This Ovago deal was found by Cheapflights users on 9/16. 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.
Fri 12/512:35 pmORF - LIR
1 stop25h 20mJetBlue
Fri 12/122:00 pmLIR - ORF
1 stop20h 49mJetBlue
Deal found 9/16$454
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 12/115:08 amORF - LIR
1 stop8h 22mAmerican Airlines
Tue 12/163:20 pmLIR - ORF
1 stop8h 08mAmerican Airlines
Deal found 9/17$461
This American Airlines deal was found by Cheapflights users on 9/16. 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
Fri 12/123:20 pmLIR - ORF
2 stops17h 08mAmerican Airlines
Deal found 9/16$465
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/116:00 amORF - LIR
1 stop7h 21mAmerican Airlines
Sun 11/161:21 pmLIR - ORF
2 stops19h 12mAmerican Airlines
Deal found 9/15$470
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 11/25:00 amORF - LIR
1 stop9h 13mAmerican Airlines
Fri 11/73:13 pmLIR - ORF
1 stop8h 02mAmerican Airlines
Deal found 9/15$551
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 11/25:21 amORF - LIR
1 stop8h 46mAmerican Airlines
Sat 11/81:21 pmLIR - ORF
1 stop9h 54mAmerican Airlines
Deal found 9/15$571
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 10/315:24 amORF - LIR
1 stop8h 16mDelta
Sat 11/82:05 pmLIR - ORF
1 stop9h 15mDelta
Deal found 9/15$600

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 September 17, 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

Mon 11/3

5:24 am-12:30 pm

1 stop8h 06m

San José Juan Santamaria Intl

Sat 11/15

1:19 pm-11:40 pm

1 stop9h 21m

$259

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/10

8:01 am-3:16 pm

1 stop8h 15m

San José Juan Santamaria Intl

Fri 11/14

7:30 am-12:07 am

1 stop15h 37m

$265

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 9/29

5:38 pm-11:14 am

2 stops19h 36m

San José Juan Santamaria Intl

Thu 10/2

12:19 pm-4:43 pm

3 stops26h 24m

$333

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/3

4:57 pm-12:30 pm

2 stops20h 33m

San José Juan Santamaria Intl

Fri 11/7

12:22 pm-12:07 am

1 stop10h 45m

$349

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 11/3

5:24 am-12:30 pm

1 stop8h 06m

San José Juan Santamaria Intl

Fri 11/14

4:08 am-11:40 pm

2 stops18h 32m

$370

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Wed 10/1

10:33 am-11:35 pm

2 stops15h 02m

San José Juan Santamaria Intl

Tue 10/7

4:20 pm-9:37 am

2 stops15h 17m

$378

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Tue 2/10

5:30 am-12:50 pm

1 stop8h 20m

Liberia

Tue 3/10

2:55 pm-11:59 pm

1 stop7h 04m

$405

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Tue 2/10

5:07 am-12:20 pm

1 stop8h 13m

Liberia

Tue 3/10

2:55 pm-11:09 am

2 stops18h 14m

$409

NorfolkSan José

ORF - SJO

ORFSJO

Norfolk

Mon 12/15

12:35 pm-8:52 am

1 stop21h 17m

San José Juan Santamaria Intl

Mon 12/29

5:31 pm-11:49 am

1 stop17h 18m

$421

NorfolkLiberia

ORF - LIR

ORFLIR

Norfolk

Mon 2/9

5:30 am-2:30 pm

1 stop10h 00m

Liberia

Mon 3/9

2:55 pm-11:59 pm

1 stop7h 04m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 17 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, 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 $554). 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 September 17, 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.

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 September 17, 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
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 06m. The distance from Chesapeake to Costa Rica is about 1923 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, 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 $554). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$259Average$396FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$320Average$476FlexibilityNo cancel feeOn-time62%
DeltaCheapest$321Average$613FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$389Average$659FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$390Average$617FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$480Average$780FlexibilityNo cancel feeOn-time63%

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