$164+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
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.Cheapflights Tip: The best prices from Chesapeake to San José Juan Santamaria Intl are usually found in September or August, booked 62 days in advance, depart on a Wednesday or Tuesday and return on a Monday
Cheap 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 June 12, 2025.
Round-trip from | $336 (Kiwi.com) |
|---|---|
One-way from | $164 (Mytrip) |
Popular in | December |
Cheapest in | September |
Average price | $668 |
Find flight deals from Chesapeake to San José
Cheapest flights from Chesapeake to San JoséExplore 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 June 12, 2025.
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 June 12, 2025.
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
This Mytrip deal was found by Cheapflights users on 6/11. 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.
This Copa Airlines deal was found by Cheapflights users on 6/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
This Avianca deal was found by Cheapflights users on 6/10. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/10. 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.
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 June 12, 2025.
Use the filters below to find and compare flights from Chesapeake to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Sun 6/29
4:14 pm-11:17 am
1 stop21h 03m
San José Juan Santamaria Intl
Wed 7/9
12:16 pm-8:15 am
1 stop17h 59m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Wed 6/25
7:32 pm-11:19 am
1 stop17h 47m
San José Juan Santamaria Intl
Tue 7/1
12:28 pm-6:37 pm
1 stop28h 09m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Wed 10/1
10:33 am-7:35 am
2 stops23h 02m
San José Juan Santamaria Intl
Tue 10/7
5:52 pm-9:37 am
2 stops13h 45m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Sun 8/31
6:50 am-6:20 pm
2 stops13h 30m
San José Juan Santamaria Intl
Thu 9/11
8:50 am-10:50 pm
2 stops12h 00m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Wed 10/1
6:10 am-11:12 am
1 stop7h 02m
San José Juan Santamaria Intl
Tue 10/7
2:25 pm-11:29 pm
1 stop7h 04m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Mon 7/7
6:10 am-7:40 am
2 stops27h 30m
San José Juan Santamaria Intl
Mon 7/14
4:20 pm-9:41 am
2 stops15h 21m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Wed 7/30
8:10 pm-10:11 am
2 stops16h 01m
San José Juan Santamaria Intl
Wed 8/6
5:30 am-10:27 pm
1 stop14h 57m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Sun 7/6
5:23 am-12:00 pm
1 stop8h 37m
San José Juan Santamaria Intl
Mon 7/14
1:21 pm-12:39 am
1 stop9h 18m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Mon 6/30
1:51 pm-3:13 pm
1 stop27h 22m
NorfolkSan José
ORF - SJO
ORFSJO
Norfolk
Mon 6/30
1:51 pm-11:19 am
2 stops23h 28m
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.
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, San José Province?
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 June 9, 2025.
The best time to book flights from Chesapeake to San José, San José Province is 61 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chesapeake to San José, San José Province?
Currently, September is the cheapest month in which you can book a flight from Chesapeake to San José, San José Province (average of $398). Flying from Chesapeake to San José, San José Province 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 SJO?
Find hourly flight availability from Chesapeake to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
When flying from Chesapeake to San José, San José Province, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
What is the cheapest day to fly from Chesapeake to San José, San José Province?
Use this chart to determine the cheapest time to fly round-trip from Chesapeake to San José. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chesapeake to San José, San José Province flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Rainfall in San José by month
Plan your trip to San José by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in San José, San José Province 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 San José, San José Province when rainfall is around 0.0 in.
Temperature in San José by month
Plan your trip to San José by taking into account the average temperature totals by month.
If weather is an important factor for your trip to San José, San José Province, 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 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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Copa Airlines from Chesapeake to San José by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Entertainment
Overall
Boarding
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Overall
Boarding
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Overall
Boarding
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Overall
Boarding
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Overall
Boarding
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
Food
Entertainment
Overall
Boarding
Comfort
Crew
Reviews
John,May 2025
PVD - BNA
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.
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Alternative routes for Chesapeake to San José
See prices for flight routes from nearby airports that may be better suited for you.
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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$247 | Average$376 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$322 | Average$487 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$333 | Average$539 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$350 | Average$628 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$389 | Average$568 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$480 | Average$732 | FlexibilityNo cancel fee | On-time63% |