$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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
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 August or October, booked 56 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 July 7, 2025.
Round-trip from | $198 (Breeze Airways) |
|---|---|
One-way from | $99 (Breeze Airways) |
Popular in | March |
Cheapest in | August |
Average price | $387 |
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 July 7, 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 July 7, 2025.
This Breeze Airways deal was found by Cheapflights users on 7/7. 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.
This Southwest deal was found by Cheapflights users on 7/7. 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.
This American Airlines deal was found by Cheapflights users on 7/7. 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 Mytrip deal was found by Cheapflights users on 7/6. 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 Delta deal was found by Cheapflights users on 7/6. 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.
This Mytrip deal was found by Cheapflights users on 7/7. 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.
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 July 7, 2025.
Use the filters below to find and compare flights from San Diego to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Fri 8/29
12:58 pm-9:20 pm
Nonstop5h 22m
Norfolk
Sat 9/6
9:21 am-12:27 pm
Nonstop6h 06m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 8/20
9:10 pm-9:10 am
1 stop9h 00m
Norfolk
Mon 8/25
6:15 pm-11:05 pm
1 stop7h 50m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 9/4
7:16 pm-10:48 pm
3 stops24h 32m
Norfolk
Sun 9/7
5:30 am-11:45 pm
3 stops21h 15m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Sat 8/30
6:15 am-4:59 pm
1 stop7h 44m
Norfolk
Sat 9/6
6:51 am-12:28 pm
1 stop8h 37m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 7/30
9:20 am-9:02 pm
1 stop8h 42m
Norfolk
Mon 8/4
3:11 pm-9:22 pm
1 stop9h 11m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 7/30
8:00 am-11:51 am
1 stop24h 51m
Norfolk
Sun 8/3
12:53 pm-11:57 pm
1 stop14h 04m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 7/30
8:00 am-11:51 am
1 stop24h 51m
Norfolk
Sun 8/3
5:20 pm-9:55 am
2 stops19h 35m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Mon 9/15
1:12 pm-9:25 pm
Nonstop5h 13m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 8/27
9:10 pm-9:10 am
1 stop9h 00m
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 9/23
10:45 pm-12:12 pm
1 stop10h 27m
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.
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 June 27, 2025.
Booking 56 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, January is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $281). Flying from San Diego to Chesapeake in March is currently the most expensive (average of $351). 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 July 7, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Diego to Chesapeake as you normally would.
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 July 6, 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.
How much does it cost to fly round-trip from San Diego to Chesapeake?
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 July 7, 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.
Boarding
Overall
Food
Entertainment
Crew
Comfort
Reviews
Dena,Dec 2024
LAS - BDL
Boarding
Overall
Food
Entertainment
Crew
Comfort
Reviews
Dena,Dec 2024
LAS - BDL
Boarding
Overall
Food
Entertainment
Crew
Comfort
Reviews
Dena,Dec 2024
LAS - BDL
Boarding
Overall
Food
Entertainment
Crew
Comfort
Reviews
Dena,Dec 2024
LAS - BDL
Boarding
Overall
Food
Entertainment
Crew
Comfort
Reviews
Dena,Dec 2024
LAS - BDL
Boarding
Overall
Food
Entertainment
Crew
Comfort
Reviews
Dena,Dec 2024
LAS - 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 6 airlines flying from San Diego to Chesapeake
Discover the top 6 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 July 7, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$300 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$270 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$206 | Average$466 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$303 | Average$477 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$356 | Average$474 | FlexibilityNo cancel fee | On-time63% |