$148+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Jul 21 — Jul 281
Round-trip
1 adult, Economy
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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
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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 October, booked 68 days in advance, depart on a Friday or Tuesday and return on a Wednesday
Cheap flight deals from Chesapeake to San Diego
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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 June 21, 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 June 21, 2026.
This Breeze Airways deal was found by Cheapflights users on 6/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Wed 8/261:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/15![Breeze Airways logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Fri 8/149:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 8/221:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/15![Breeze Airways logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 8/129:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 8/221:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/15![Breeze Airways logo]()
$332
This Breeze Airways deal was found by Cheapflights users on 6/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Mon 8/241:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/16![Breeze Airways logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Fri 8/149:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Fri 8/211:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/15![Breeze Airways logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Sat 8/159:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 8/189:53 pm
SAN
- ORF
2 stops34h 33m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Sat 8/229:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Wed 8/269:37 am
SAN
- ORF
2 stops22h 49m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 8/129:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Fri 8/211:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/15![Breeze Airways logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Sat 8/159:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Wed 8/199:37 am
SAN
- ORF
2 stops22h 49m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Wed 7/229:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Wed 7/293:03 pm
SAN
- ORF
2 stops17h 12m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 6/15. 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 8/1110:20 am
ORF
- SAN
1 stop9h 45m
Delta
Tue 8/182:00 pm
SAN
- ORF
1 stop7h 06m
Delta
Deal found 6/15![Delta logo]()
$363
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 June 21, 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 June 21, 2026.
This Southwest deal was found by Cheapflights users on 6/20. 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 8/1112:15 pm
ORF
- SAN
2 stops9h 40m
Southwest
Wed 8/1910:40 pm
SAN
- ORF
1 stop7h 50m
Southwest
Deal found 6/20![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 7/312:07 pm
ORF
- SAN
1 stop11h 27m
Delta
Sat 7/48:00 am
SAN
- ORF
1 stop8h 44m
Delta
Deal found 6/17![Delta logo]()
$403
This Breeze Airways deal was found by Cheapflights users on 6/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Mon 8/101:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/16![Breeze Airways logo]()
$453
This Southwest deal was found by Cheapflights users on 6/20. 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 8/2410:10 am
ORF
- SAN
2 stops11h 00m
Southwest
Sat 8/2910:40 pm
SAN
- ORF
2 stops10h 55m
Southwest
Deal found 6/20![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:35 pm
ORF
- SAN
1 stop7h 23m
Delta
Mon 8/1010:25 pm
SAN
- ORF
1 stop7h 48m
Delta
Deal found 6/16![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 6/18. 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 8/156:00 am
ORF
- SAN
2 stops9h 40m
Southwest
Sat 8/2210:40 pm
SAN
- ORF
2 stops10h 55m
Southwest
Deal found 6/18![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 6/19. 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.
Wed 7/810:16 am
ORF
- SAN
1 stop9h 44m
Delta
Wed 7/152:18 pm
SAN
- ORF
1 stop7h 27m
Delta
Deal found 6/19![Delta logo]()
$441
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:25 pm
ORF
- SAN
2 stops10h 10m
Southwest
Wed 7/221:10 pm
SAN
- ORF
1 stop8h 40m
Southwest
Deal found 6/16![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 6/20. 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 8/286:45 pm
ORF
- SAN
1 stop7h 10m
Southwest
Mon 8/319:00 pm
SAN
- ORF
2 stops9h 15m
Southwest
Deal found 6/20![Southwest logo]()
$434
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/63:45 pm
ORF
- SAN
2 stops9h 10m
Southwest
Sun 8/910:40 pm
SAN
- ORF
1 stop7h 50m
Southwest
Deal found 6/17![Southwest logo]()
$448
Last-minute flights from Chesapeake to San DiegoDiscover last-minute flight deals from Chesapeake to San Diego. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to San Diego. Data last updated June 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Fri 6/269:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 7/41:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/16![Breeze Airways logo]()
$373
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:05 am
ORF
- SAN
1 stop6h 59m
American Airlines
Wed 7/159:55 pm
SAN
- ORF
1 stop9h 34m
American Airlines
Deal found 6/16![American Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/1412:10 pm
ORF
- SAN
2 stops14h 54m
Multiple Airlines
Fri 7/171:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:56 pm
ORF
- SAN
1 stop8h 03m
American Airlines
Tue 7/216:15 am
SAN
- ORF
1 stop7h 37m
American Airlines
Deal found 6/16![American Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:30 pm
ORF
- SAN
1 stop10h 00m
Southwest
Tue 7/2110:40 pm
SAN
- ORF
2 stops10h 20m
Southwest
Deal found 6/16![Southwest logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/159:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Fri 7/171:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/17![Breeze Airways logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/1512:10 pm
ORF
- SAN
2 stops23h 55m
Multiple Airlines
Sat 7/181:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/159:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 7/214:12 pm
SAN
- ORF
3 stops16h 03m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/159:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Thu 7/164:12 pm
SAN
- ORF
2 stops25h 27m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Mon 7/209:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Mon 7/208:51 pm
SAN
- ORF
2 stops20h 48m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Wed 7/229:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Wed 7/293:03 pm
SAN
- ORF
2 stops17h 12m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 6/15. 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 7/295:15 am
ORF
- SAN
2 stops10h 00m
Southwest
Tue 8/410:40 pm
SAN
- ORF
1 stop10h 25m
Southwest
Deal found 6/15![Southwest logo]()
$374
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 June 21, 2026.
Search for one-way flight options from Chesapeake to San Diego. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/159:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 6/17![Breeze Airways logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/1412:10 pm
ORF
- SAN
2 stops14h 54m
Frontier
Deal found 6/19![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/159:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 6/18![Breeze Airways logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/2012:21 pm
ORF
- SAN
2 stops29h 29m
Frontier
Deal found 6/19![Frontier logo]()
$180
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Tue 7/146:46 pm
ORF
- SAN
1 stop7h 40m
American Airlines
Deal found 6/19![American Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Wed 7/229:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 6/16![Breeze Airways logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/812:10 pm
ORF
- SAN
2 stops23h 55m
Frontier
Deal found 6/17![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:30 pm
ORF
- SAN
2 stops9h 55m
Southwest
Deal found 6/16![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/1512:16 pm
ORF
- SAN
2 stops14h 43m
Frontier
Deal found 6/17![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Sun 7/269:34 pm
ORF
- SAN
2 stops43h 34m
Frontier
Deal found 6/18![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/2212:00 pm
ORF
- SAN
2 stops23h 42m
Frontier
Deal found 6/16![Frontier logo]()
$194
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 June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (Breeze Airways) |
One-way from | $148 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $512 |
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 June 21, 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 - SAN
ORFSAN
Norfolk
Tue 8/11
12:15 pm-6:55 pm
2 stops9h 40m
San Diego
Wed 8/19
10:40 pm-9:30 am
1 stop7h 50m
$396
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 7/3
12:07 pm-8:34 pm
1 stop11h 27m
San Diego
Sat 7/4
8:00 am-7:44 pm
1 stop8h 44m
$403
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 8/24
10:10 am-6:10 pm
2 stops11h 00m
San Diego
Sat 8/29
10:40 pm-12:35 pm
2 stops10h 55m
$429
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 8/3
4:35 pm-8:58 pm
1 stop7h 23m
San Diego
Mon 8/10
10:25 pm-9:13 am
1 stop7h 48m
$429
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sat 8/15
6:00 am-12:40 pm
2 stops9h 40m
San Diego
Sat 8/22
10:40 pm-12:35 pm
2 stops10h 55m
$429
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Wed 7/1
12:25 pm-7:35 pm
2 stops10h 10m
San Diego
Wed 7/22
1:10 pm-12:50 am
1 stop8h 40m
$433
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 8/28
6:45 pm-10:55 pm
1 stop7h 10m
San Diego
Mon 8/31
9:00 pm-9:15 am
2 stops9h 15m
$434
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Wed 7/8
10:16 am-5:00 pm
1 stop9h 44m
San Diego
Wed 7/15
2:18 pm-12:45 am
1 stop7h 27m
$441
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Thu 8/6
3:45 pm-9:55 pm
2 stops9h 10m
San Diego
Sun 8/9
10:40 pm-9:30 am
1 stop7h 50m
$448
Quickest round-trip
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 8/3
9:38 am-12:20 pm
Nonstop5h 42m
San Diego
Mon 8/10
1:05 pm-9:28 pm
Nonstop5h 23m
$453
Showing 1-10 of 22 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 June 21, 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?
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 June 21, 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.
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.4
Crew
8.8
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.4
Crew
8.8
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.4
Crew
8.8
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.4
Crew
8.8
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.4
Crew
8.8
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.4
Crew
8.8
Overall
8.2
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
Poway
Coronado
La Mesa
Santee
Julian
Lemon Grove
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Chesapeake and San Diego flights
Browse other Chesapeake and San Diego flight options. Last updated on June 21, 2026.
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Explore flights to San Diego departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 21, 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 2,558,603 searches. Data last updated June 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$347 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$471 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$272 | Average$467 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$296 | Average$528 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$303 | Average$570 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$332 | Average$506 | FlexibilityNo cancel fee | On-time63% |