$128+ Cheap flights from Chesapeake, VA to San Diego (SAN)
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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Oct 17 — Oct 241
Round-trip
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 October or November, booked 78 days in advance, depart on a Thursday or Tuesday and return on a Wednesday
Cheap flight deals from Chesapeake to San Diego
Cheapest
Best
Last-minute
One-way
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 September 17, 2026.
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 September 17, 2026.
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.
Sat 10/105:25 pm -
1 stop7h 37m
Tue 10/132:10 pm -
1 stop7h 35m
Deal found 9/15![Delta logo]()
$305
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:15 am -
1 stop8h 10m
Wed 10/2111:19 am -
2 stops9h 25m
Deal found 9/16![United Airlines logo]()
$310
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:10 pm -
1 stop7h 20m
Sat 11/147:00 am -
2 stops11h 20m
Deal found 9/15![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/204:45 pm -
2 stops9h 35m
Sat 10/246:30 am -
1 stop9h 45m
Deal found 9/14![Southwest logo]()
$312
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:15 am -
2 stops10h 15m
Tue 11/108:00 am -
2 stops10h 15m
Deal found 9/15![Southwest logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/319:22 am -
Nonstop6h 06m
Sat 11/710:56 am -
3 stops22h 50m
Deal found 9/13![Multiple Airlines logo]()
$316
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:38 am -
1 stop27h 33m
Sat 11/71:13 pm -
Nonstop5h 06m
Deal found 9/15![Multiple Airlines logo]()
$320
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:05 pm -
1 stop9h 10m
Wed 10/289:50 pm -
1 stop8h 25m
Deal found 9/15![Southwest logo]()
$321
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop9h 44m
Thu 10/2911:31 am -
1 stop9h 01m
Deal found 9/17![Delta logo]()
$327
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:35 pm -
1 stop8h 45m
Tue 11/106:35 am -
1 stop7h 50m
Deal found 9/15![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/274:45 pm -
1 stop7h 40m
Fri 10/309:50 pm -
1 stop8h 15m
Deal found 9/14![Southwest logo]()
$331
Best flights from Chesapeake to San DiegoDiscover carefully curated flight deals from Chesapeake to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Chesapeake to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
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.
Sat 10/105:25 pm -
1 stop7h 37m
Tue 10/132:10 pm -
1 stop7h 35m
Deal found 9/15![Delta logo]()
$305
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:05 pm -
1 stop9h 10m
Wed 10/289:50 pm -
1 stop8h 25m
Deal found 9/15![Southwest logo]()
$321
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:01 pm -
1 stop8h 40m
Tue 10/136:28 pm -
2 stops14h 47m
Deal found 9/15![United Airlines logo]()
$463
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:05 pm -
2 stops9h 50m
Mon 11/169:55 pm -
1 stop8h 15m
Deal found 9/15![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 9/295:35 pm -
1 stop8h 59m
Sat 10/311:30 am -
1 stop9h 03m
Deal found 9/12![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 9/291:07 pm -
1 stop9h 19m
Tue 10/62:10 pm -
1 stop7h 35m
Deal found 9/12![Delta logo]()
$389
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:45 pm -
2 stops9h 35m
Sun 10/2510:40 pm -
1 stop9h 20m
Deal found 9/15![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 12/35:31 pm -
1 stop9h 27m
Sun 12/610:30 pm -
1 stop8h 25m
Deal found 9/13![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 10/319:40 am -
2 stops10h 45m
Sat 11/77:15 am -
2 stops11h 05m
Deal found 9/13![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/72:45 pm -
1 stop9h 40m
Sat 10/1010:40 pm -
2 stops10h 15m
Deal found 9/13![Southwest logo]()
$463
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 9/285:35 pm -
1 stop8h 59m
Thu 10/19:59 pm -
1 stop10h 27m
Deal found 9/14![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/2312:10 pm -
2 stops10h 35m
Mon 10/2610:15 am -
2 stops8h 35m
Deal found 9/14![Southwest logo]()
$487
Last-minute flights from Chesapeake to San DiegoDiscover last-minute flight deals from Chesapeake to San Diego. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to San Diego. Data last updated September 17, 2026 and is based on user searches.
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.
Fri 10/22:49 pm -
1 stop7h 28m
Tue 10/61:11 pm -
1 stop6h 34m
Deal found 9/15![American Airlines logo]()
$337
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.
Sat 10/105:25 pm -
1 stop7h 37m
Tue 10/132:10 pm -
1 stop7h 35m
Deal found 9/15![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 10/1312:05 pm -
1 stop14h 05m
Mon 10/199:50 pm -
1 stop8h 30m
Deal found 9/13![Southwest logo]()
$333
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:15 am -
1 stop8h 10m
Wed 10/2111:19 am -
2 stops9h 25m
Deal found 9/16![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/204:45 pm -
2 stops9h 35m
Sat 10/246:30 am -
1 stop9h 45m
Deal found 9/14![Southwest logo]()
$312
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:05 pm -
1 stop9h 10m
Wed 10/289:50 pm -
1 stop8h 25m
Deal found 9/15![Southwest logo]()
$321
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop9h 44m
Thu 10/2911:31 am -
1 stop9h 01m
Deal found 9/17![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/274:45 pm -
1 stop7h 40m
Fri 10/309:50 pm -
1 stop8h 15m
Deal found 9/14![Southwest logo]()
$331
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:00 am -
1 stop7h 56m
Sat 10/3111:21 am -
2 stops9h 23m
Deal found 9/16![United Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/319:22 am -
Nonstop6h 06m
Sat 11/710:56 am -
3 stops22h 50m
Deal found 9/13![Multiple Airlines logo]()
$316
One-way flights from Chesapeake to San DiegoSearch for one-way flight options from Chesapeake to San Diego. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Chesapeake to San Diego. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
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.
Sat 11/149:22 am -
Nonstop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/79:22 am -
Nonstop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Breeze Airways logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/73:50 pm -
2 stops11h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$152
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.
Tue 10/135:30 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Tue 10/201:19 pm -
2 stops29h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$158
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 10/1312:05 pm -
1 stop14h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$159
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:22 am -
Nonstop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Breeze Airways logo]()
$163
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$169
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:23 pm -
2 stops22h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 9/13. 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.
Mon 10/196:05 pm -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 10/131:19 pm -
2 stops13h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$177
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.
Thu 10/157:07 pm -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$178
Find 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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (American Airlines) |
One-way from | $128 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $460 |
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 7,457,451 searches. Data last updated September 17, 2026.
Use the filters below to find and compare flights from Chesapeake to San Diego that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Wed 12/2
5:26 pm-11:39 pm
1 stop9h 13m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$153
Quickest round-trip
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Tue 10/13
5:30 am-9:42 am
1 stop7h 12m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$153
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Wed 10/14
7:00 am-11:13 am
1 stop7h 13m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$153
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Sat 10/10
5:25 pm-10:02 pm
1 stop7h 37m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$153
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Mon 10/19
6:05 pm-12:15 am
1 stop9h 10m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$175
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Wed 12/2
3:05 pm-9:55 pm
2 stops9h 50m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$180
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Wed 11/4
3:13 pm-10:02 pm
1 stop9h 49m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$185
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Sat 10/17
6:00 am-10:20 am
1 stop7h 20m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$185
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Wed 11/4
8:55 am-4:05 pm
2 stops10h 10m
San Diego
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$190
NorfolkSan Diego
ORF Norfolk - SAN San Diego
ORFSAN
Norfolk
Sat 10/10
5:25 pm-10:02 pm
1 stop7h 37m
San Diego
Tue 10/13
2:10 pm-12:45 am
1 stop7h 35m
$305
Showing 1-10 of 21 resultsSorted by cheapest first
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.
ORF-SAN
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
C6E-SAN
ORF-SAN
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 September 17, 2026.
When flying from Chesapeake to San Diego, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chesapeake to San Diego?
Airfare is below average for this route at the moment.
Chesapeake to San Diego flights typically cost between $338 and $554 in October.The cheapest round-trip price found within the last 5 days was $305 on Delta (Oct 10-Oct 13).
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 September 17, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andDelta 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.
Comfort
8.2
Crew
8.8
Food
6.8
Entertainment
6.8
Overall
8.2
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Crew
8.8
Food
6.8
Entertainment
6.8
Overall
8.2
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Crew
8.8
Food
6.8
Entertainment
6.8
Overall
8.2
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Crew
8.8
Food
6.8
Entertainment
6.8
Overall
8.2
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Crew
8.8
Food
6.8
Entertainment
6.8
Overall
8.2
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Crew
8.8
Food
6.8
Entertainment
6.8
Overall
8.2
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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
National City
Chula Vista
Coronado
San Ysidro
Poway
La Mesa
Santee
Julian
Lemon Grove
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
San Diego flight routes
Top destinations
Alternative routes for Chesapeake to San Diego
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Diego by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chesapeake to San Diego by cabin class
Find flights from Chesapeake to San Diego, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chesapeake and San Diego flights
Browse other Chesapeake and San Diego flight options. Last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San Diego
Explore flights to San Diego departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Chesapeake to San Diego flights
Consider these flights traveling from Chesapeake to San Diego.
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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$147 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$389 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$179 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$511 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$283 | Average$455 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$318 | Average$581 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$358 | Average$512 | FlexibilityNo cancel fee | On-time63% |