$99+ Cheap flights from Chesapeake, VA to San Diego (SAN)
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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Nov 27 — Dec 41
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chesapeake to San Diego 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 Diego are usually found in August or May, booked 68 days in advance, depart on a Tuesday or Friday and return on a Tuesday
Cheap flight deals from Chesapeake to San Diego
Keep the following information in mind while searching for Chesapeake to San Diego flight deals. Data was last updated October 28, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $258 (Breeze Airways) |
One-way from | $99 (Breeze Airways) |
Popular in | March |
Cheapest in | August |
Average price | $358 |
Find flight deals from Chesapeake to San Diego
Cheapest flights from Chesapeake to San DiegoExplore the most affordable flight options available from Chesapeake to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.
Explore the most affordable flight options available from Chesapeake to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.
This Breeze Airways deal was found by Cheapflights users on 10/25. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/129:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Wed 11/191:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 10/25![Breeze Airways logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 11/159:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Mon 11/171:20 pmSAN - ORF
2 stops25h 18mMultiple Airlines
Deal found 10/26![Multiple Airlines logo]()
$260
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Fri 11/141:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 10/26![Breeze Airways logo]()
$267
This Breeze Airways deal was found by Cheapflights users on 10/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Mon 11/171:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 10/28![Breeze Airways logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Fri 12/129:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Sun 12/144:47 pmSAN - ORF
2 stops20h 33mMultiple Airlines
Deal found 10/26![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/159:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Fri 12/267:21 pmSAN - ORF
2 stops18h 06mMultiple Airlines
Deal found 10/26![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/1011:42 amORF - SAN
3 stops27h 25mMultiple Airlines
Fri 11/141:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
Deal found 10/26![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/89:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Wed 11/121:37 pmSAN - ORF
3 stops20h 38mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:42 pmORF - SAN
2 stops40h 12mMultiple Airlines
Wed 12/31:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Thu 11/208:39 amSAN - ORF
2 stops31h 28mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Fri 10/319:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Wed 11/51:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 10/26![Breeze Airways logo]()
$295
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to San Diego 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 October 28, 2025.
Use the filters below to find and compare flights from Chesapeake to San Diego that are best for you.
Fly from
Chesapeake
Fly to
San Diego
Route
Depart
Return
Price
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sat 11/15
9:21 am-12:27 pm
Nonstop6h 06m
San Diego
Mon 11/17
1:12 pm-9:25 pm
Nonstop5h 13m
$258
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 11/14
9:21 am-12:27 pm
Nonstop6h 06m
San Diego
Mon 11/17
1:12 pm-9:25 pm
Nonstop5h 13m
$258
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sat 11/8
9:21 am-12:27 pm
Nonstop6h 06m
San Diego
Wed 11/12
1:12 pm-9:25 pm
Nonstop5h 13m
$258
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sat 12/6
9:21 am-12:27 pm
Nonstop6h 06m
San Diego
Sat 12/20
1:12 pm-9:25 pm
Nonstop5h 13m
$328
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 11/14
3:11 pm-9:13 pm
1 stop9h 02m
San Diego
Mon 11/17
10:30 pm-9:19 am
1 stop7h 49m
$337
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 12/15
9:21 am-12:27 pm
Nonstop6h 06m
San Diego
Fri 12/26
1:12 pm-9:25 pm
Nonstop5h 13m
$338
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 1/5
5:30 am-10:10 am
1 stop7h 40m
San Diego
Mon 1/19
9:45 pm-9:40 am
1 stop8h 55m
$359
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Wed 1/7
1:01 pm-7:00 pm
1 stop8h 59m
San Diego
Wed 1/21
6:15 am-5:13 pm
1 stop7h 58m
$359
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sat 12/13
9:21 am-12:27 pm
Nonstop6h 06m
$99
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 12/12
9:21 am-12:27 pm
Nonstop6h 06m
$99
Showing 1-10 of 17 results
Best time to book a flight from Chesapeake to San Diego
Have a flexible travel schedule? Discover the best time to fly to San Diego 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 San Diego
How far ahead should I book a flight from Chesapeake to San Diego?
Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to San Diego. Price data was last updated on October 24, 2025.
The price you pay for your flight from Chesapeake to San Diego may vary depending on when you book. For the best chance of a lower fare, look to book 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chesapeake to San Diego?
Currently, September is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $127). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $332). 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 SAN?
Find hourly flight availability from Chesapeake to San Diego. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.
It’s optimal to fly from Chesapeake to San Diego in the morning. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Chesapeake to San Diego?
Use this chart to determine the cheapest time to fly round-trip from Chesapeake to San Diego. Price data was last updated on October 26, 2025.
Travelers seeking maximum savings on their Chesapeake to San Diego flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing San Diego
Get insights into the airlines that provide service to San Diego. 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 Diego. Reviews last updated October 28, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and Delta from Chesapeake to San Diego by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.1
Food
6.7
Entertainment
6.6
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Overall
8.1
Food
6.7
Entertainment
6.6
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Overall
8.1
Food
6.7
Entertainment
6.6
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Overall
8.1
Food
6.7
Entertainment
6.6
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Overall
8.1
Food
6.7
Entertainment
6.6
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Overall
8.1
Food
6.7
Entertainment
6.6
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to San Diego. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Diego?
Book flights to San Diego if you plan to visit one of these locationsEl Cajon
Chula Vista
Coronado
La Mesa
Poway
Lemon Grove
National City
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chesapeake to San Diego
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chesapeake to San Diego
Discover the top 7 airlines that operate flights from Chesapeake to San Diego. 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 October 28, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$127 | Average$252 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$143 | Average$266 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$198 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$457 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$479 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$533 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$473 | FlexibilityNo cancel fee | On-time63% |