$99+ Cheap flights from San Diego (SAN) to Chesapeake, VA
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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
nov. 27 — dic. 41
1 adult, Economy
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Find cheap flights from San Diego to Chesapeake 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 San Diego to Chesapeake are usually found in May or August, booked 90 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
Cheap flight deals from San Diego to Chesapeake
Keep the following information in mind while searching for San Diego to Chesapeake flight deals. Data was last updated octubre 28, 2025.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $240 (Kiwi.com) |
One-way from | $99 (Breeze Airways) |
Popular in | March |
Cheapest in | May |
Average price | $391 |
Find flight deals from San Diego to Chesapeake
Cheapest flights from San Diego to ChesapeakeExplore the most affordable flight options available from San Diego to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 28, 2025.
Explore the most affordable flight options available from San Diego to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 28, 2025.
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.
vie. 12/51:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
lun. 12/810:05 pmORF - SAN
2 stops17h 31mBreeze Airways
Deal found 10/26![Breeze Airways logo]()
$240
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.
mié. 12/36:25 amSAN - ORF
3 stops22h 18mMultiple Airlines
lun. 12/89:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Deal found 10/26![Multiple Airlines logo]()
$241
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.
mar. 12/91:21 pmSAN - ORF
2 stops16h 15mBreeze Airways
lun. 12/159:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 10/27![Breeze Airways logo]()
$244
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.
vie. 12/51:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
mié. 12/1010:05 pmORF - SAN
2 stops17h 31mBreeze Airways
Deal found 10/27![Breeze Airways logo]()
$254
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.
dom. 12/72:02 pmSAN - ORF
2 stops23h 18mMultiple Airlines
lun. 12/159:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$255
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/141:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
lun. 11/179:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 10/26![Breeze Airways logo]()
$258
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.
vie. 12/51:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
lun. 12/1510:05 pmORF - SAN
2 stops17h 31mBreeze Airways
Deal found 10/27![Breeze Airways logo]()
$263
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.
vie. 12/51:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
lun. 12/87:00 amORF - SAN
3 stops19h 59mMultiple Airlines
Deal found 10/26![Multiple Airlines logo]()
$265
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.
lun. 12/84:57 pmSAN - ORF
2 stops19h 44mMultiple Airlines
sáb. 12/139:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$269
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.
vie. 12/51:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
jue. 12/118:38 amORF - SAN
3 stops18h 21mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$272
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.
vie. 12/54:47 pmSAN - ORF
3 stops23h 29mMultiple Airlines
vie. 12/129:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Deal found 10/27![Multiple Airlines logo]()
$273
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.
sáb. 11/151:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
lun. 11/179:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 10/26![Breeze Airways logo]()
$274
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Chesapeake 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 octubre 28, 2025.
Use the filters below to find and compare flights from San Diego to Chesapeake that are best for you.
Fly from
San Diego
Fly to
Chesapeake
Route
Depart
Return
Price
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
lun. 11/10
9:50 pm-9:19 am
1 stop8h 29m
Norfolk
vie. 11/14
4:58 pm-10:20 pm
1 stop8h 22m
$337
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
vie. 12/5
6:15 am-4:57 pm
1 stop7h 42m
Norfolk
sáb. 12/13
12:12 pm-6:18 pm
1 stop9h 06m
$337
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
vie. 12/5
12:24 pm-11:29 pm
1 stop8h 05m
Norfolk
vie. 12/12
8:30 am-1:02 pm
1 stop7h 32m
$337
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
mié. 12/10
11:05 am-10:30 pm
1 stop8h 25m
Norfolk
sáb. 12/13
8:30 am-1:02 pm
1 stop7h 32m
$337
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
mié. 12/10
12:24 pm-10:30 pm
1 stop7h 06m
Norfolk
lun. 12/15
5:47 pm-11:58 pm
1 stop9h 11m
$337
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
sáb. 1/10
8:00 am-7:29 pm
1 stop8h 29m
Norfolk
sáb. 1/17
3:04 pm-7:41 pm
1 stop7h 37m
$341
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
vie. 12/5
12:00 pm-10:00 pm
1 stop7h 00m
Norfolk
vie. 12/12
5:30 am-11:30 am
2 stops9h 00m
$342
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
jue. 12/11
2:19 pm-12:32 am
1 stop7h 13m
Norfolk
vie. 12/12
8:30 am-1:02 pm
1 stop7h 32m
$348
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
lun. 12/8
10:30 pm-9:33 am
1 stop8h 03m
Norfolk
mar. 12/16
10:38 am-3:21 pm
1 stop7h 43m
$348
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
mar. 12/9
2:19 pm-12:32 am
1 stop7h 13m
Norfolk
sáb. 12/13
5:30 am-9:54 am
1 stop7h 24m
$348
Showing 1-10 of 22 results
Best time to book a flight from San Diego to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from San Diego 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 San Diego to Chesapeake
How far ahead should I book a flight from San Diego to Chesapeake?
Use this chart to determine the optimal time to book a round-trip flight from San Diego to Chesapeake. Price data was last updated on October 24, 2025.
Booking 90 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Diego to Chesapeake. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from San Diego to Chesapeake?
Currently, May is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $122). Flying from San Diego to Chesapeake in January is currently the most expensive (average of $294). 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 SAN to C6E?
Find hourly flight availability from San Diego to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 28, 2025.
A simple way to save on the total cost of your ticket is to fly from San Diego to Chesapeake in the afternoon. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from San Diego to Chesapeake?
Use this chart to determine the cheapest time to fly round-trip from San Diego to Chesapeake. Price data was last updated on October 26, 2025.
Travelers seeking maximum savings on their San Diego to Chesapeake flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated octubre 28, 2025.
Read reviews from past customers who have flown Breeze Airways, Southwest, and Delta from San Diego to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Crew
8.7
Entertainment
6.6
Comfort
8.1
Boarding
8.3
Overall
8.1
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Food
6.7
Crew
8.7
Entertainment
6.6
Comfort
8.1
Boarding
8.3
Overall
8.1
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Food
6.7
Crew
8.7
Entertainment
6.6
Comfort
8.1
Boarding
8.3
Overall
8.1
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Food
6.7
Crew
8.7
Entertainment
6.6
Comfort
8.1
Boarding
8.3
Overall
8.1
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Food
6.7
Crew
8.7
Entertainment
6.6
Comfort
8.1
Boarding
8.3
Overall
8.1
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Food
6.7
Crew
8.7
Entertainment
6.6
Comfort
8.1
Boarding
8.3
Overall
8.1
Reviews
1 / 13
8.0
ExcellentAnonymous,Jul 2025
RIC - BDL
Related info for your journey
Find useful and relevant information for your journey from San Diego to Chesapeake. 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 San Diego to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from San Diego to Chesapeake
Discover the top 5 airlines that operate flights from San Diego to Chesapeake. 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 octubre 28, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$146 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$206 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$308 | Average$474 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$312 | Average$491 | FlexibilityNo cancel fee | On-time71% |