$118+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Sep 3 — Sep 101
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
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 August, booked 50 days in advance, depart on a Friday 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 August 4, 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 August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/251:20 pm
ORF
- SAN
2 stops29h 21m
Multiple Airlines
Fri 8/281:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/1![Breeze Airways logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/241:20 pm
ORF
- SAN
2 stops53h 21m
Multiple Airlines
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/269:22 am
ORF
- SAN
Nonstop6h 06m
Multiple Airlines
Wed 9/305:54 pm
SAN
- ORF
2 stops19h 36m
Multiple Airlines
Deal found 8/3![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/291:18 pm
ORF
- SAN
2 stops13h 33m
Multiple Airlines
Wed 10/71:13 pm
SAN
- ORF
Nonstop5h 06m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 7/31. 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
Mon 8/311:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 7/31![Breeze Airways logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/3. 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
Fri 8/281:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/211:20 pm
ORF
- SAN
3 stops33h 55m
Multiple Airlines
Fri 8/281:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/29:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Mon 9/78:59 pm
SAN
- ORF
3 stops16h 12m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$295
This Booking.com deal was found by Cheapflights users on 7/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Wed 8/261:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 7/31![Breeze Airways logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/1![Breeze Airways logo]()
$297
This Breeze Airways deal was found by Cheapflights users on 8/3. 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
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$298
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 August 4, 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 August 4, 2026.
This Delta deal was found by Cheapflights users on 8/3. 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 1/283:05 pm
ORF
- SAN
1 stop9h 36m
Delta
Wed 2/32:00 pm
SAN
- ORF
1 stop7h 06m
Delta
Deal found 8/3![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 7/30. 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 8/273:45 pm
ORF
- SAN
2 stops9h 10m
Southwest
Thu 9/36:45 am
SAN
- ORF
1 stop12h 15m
Southwest
Deal found 7/30![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 9/410:41 am
ORF
- SAN
1 stop7h 16m
United Airlines
Sat 9/511:00 am
SAN
- ORF
2 stops9h 47m
United Airlines
Deal found 7/31![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 8/3. 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 9/264:00 pm
ORF
- SAN
2 stops10h 00m
Southwest
Sat 10/38:10 am
SAN
- ORF
2 stops9h 20m
Southwest
Deal found 8/3![Southwest logo]()
$397
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/106:05 am
ORF
- SAN
1 stop8h 20m
United Airlines
Sun 9/139:45 pm
SAN
- ORF
2 stops9h 08m
United Airlines
Deal found 7/31![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 7/31. 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 10/215:30 am
ORF
- SAN
1 stop7h 12m
Delta
Sun 10/2510:05 pm
SAN
- ORF
1 stop10h 23m
Delta
Deal found 7/31![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 8/3. 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 9/112:15 pm
ORF
- SAN
2 stops9h 40m
Southwest
Wed 9/29:05 am
SAN
- ORF
2 stops8h 25m
Southwest
Deal found 8/3![Southwest logo]()
$397
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/274:13 pm
ORF
- SAN
1 stop7h 21m
United Airlines
Mon 8/317:41 pm
SAN
- ORF
2 stops12h 04m
United Airlines
Deal found 7/30![United Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 8/3. 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 9/98:50 am
ORF
- SAN
2 stops9h 05m
Southwest
Sun 9/137:55 pm
SAN
- ORF
2 stops10h 35m
Southwest
Deal found 8/3![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 7/31. 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 11/24:35 pm
ORF
- SAN
2 stops10h 15m
Southwest
Fri 11/68:30 pm
SAN
- ORF
2 stops10h 15m
Southwest
Deal found 7/31![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 8/3. 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 10/1512:10 pm
ORF
- SAN
2 stops10h 35m
Southwest
Mon 10/1911:20 am
SAN
- ORF
2 stops9h 15m
Southwest
Deal found 8/3![Southwest logo]()
$427
Last-minute flights from Chesapeake to San DiegoDiscover last-minute flight deals from Chesapeake to San Diego. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to San Diego. Data last updated August 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/31. 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
Mon 8/311:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 7/31![Breeze Airways logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/3. 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
Fri 8/281:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 8/1. 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
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/1![Breeze Airways logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/1![Breeze Airways logo]()
$283
This Booking.com deal was found by Cheapflights users on 7/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Wed 8/261:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 7/31![Breeze Airways logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/211:20 pm
ORF
- SAN
3 stops33h 55m
Multiple Airlines
Fri 8/281:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$294
This Breeze Airways deal was found by Cheapflights users on 8/3. 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
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/241:20 pm
ORF
- SAN
2 stops53h 21m
Multiple Airlines
Sat 8/291:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/251:20 pm
ORF
- SAN
2 stops29h 21m
Multiple Airlines
Fri 8/281:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/29:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Mon 9/78:59 pm
SAN
- ORF
3 stops16h 12m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/269:22 am
ORF
- SAN
Nonstop6h 06m
Multiple Airlines
Wed 9/305:54 pm
SAN
- ORF
2 stops19h 36m
Multiple Airlines
Deal found 8/3![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/291:18 pm
ORF
- SAN
2 stops13h 33m
Multiple Airlines
Wed 10/71:13 pm
SAN
- ORF
Nonstop5h 06m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$291
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 August 4, 2026.
Search for one-way flight options from Chesapeake to San Diego. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 10/39:22 am
ORF
- SAN
Nonstop6h 06m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/269:22 am
ORF
- SAN
Nonstop6h 06m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/301:20 pm
ORF
- SAN
2 stops37h 31m
Frontier
Deal found 8/2![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/299:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 7/31![Breeze Airways logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 10/41:18 pm
ORF
- SAN
2 stops29h 40m
Frontier
Deal found 8/2![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/11:20 pm
ORF
- SAN
2 stops22h 45m
Frontier
Deal found 8/3![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/271:18 pm
ORF
- SAN
2 stops29h 40m
Frontier
Deal found 8/3![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.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 7/30![Breeze Airways logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/249:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 8/3![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/291:20 pm
ORF
- SAN
2 stops22h 45m
Frontier
Deal found 7/31![Frontier logo]()
$146
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Kiwi.com) |
One-way from | $118 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $369 |
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 August 4, 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
Quickest round-trip
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Thu 1/28
3:05 pm-9:41 pm
1 stop9h 36m
San Diego
Wed 2/3
2:00 pm-12:06 am
1 stop7h 06m
$357
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Thu 8/27
3:45 pm-9:55 pm
2 stops9h 10m
San Diego
Thu 9/3
6:45 am-10:00 pm
1 stop12h 15m
$379
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 9/4
10:41 am-2:57 pm
1 stop7h 16m
San Diego
Sat 9/5
11:00 am-11:47 pm
2 stops9h 47m
$385
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sat 9/26
4:00 pm-11:00 pm
2 stops10h 00m
San Diego
Sat 10/3
8:10 am-8:30 pm
2 stops9h 20m
$397
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Tue 9/1
12:15 pm-6:55 pm
2 stops9h 40m
San Diego
Wed 9/2
9:05 am-8:30 pm
2 stops8h 25m
$397
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Thu 9/10
6:05 am-11:25 am
1 stop8h 20m
San Diego
Sun 9/13
9:45 pm-9:53 am
2 stops9h 08m
$408
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Wed 9/9
8:50 am-2:55 pm
2 stops9h 05m
San Diego
Sun 9/13
7:55 pm-9:30 am
2 stops10h 35m
$413
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Wed 10/21
5:30 am-9:42 am
1 stop7h 12m
San Diego
Sun 10/25
10:05 pm-11:28 am
1 stop10h 23m
$417
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 11/2
4:35 pm-11:50 pm
2 stops10h 15m
San Diego
Fri 11/6
8:30 pm-9:45 am
2 stops10h 15m
$418
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Thu 10/15
12:10 pm-7:45 pm
2 stops10h 35m
San Diego
Mon 10/19
11:20 am-11:35 pm
2 stops9h 15m
$427
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 August 4, 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 $299 and $488 in August.The cheapest round-trip price found within the last 5 days was $281 on Multiple Airlines (Aug 25-Aug 28).
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 August 4, 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
Boarding
8.3
Food
6.7
Crew
8.7
Entertainment
6.7
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Food
6.7
Crew
8.7
Entertainment
6.7
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Food
6.7
Crew
8.7
Entertainment
6.7
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Food
6.7
Crew
8.7
Entertainment
6.7
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Food
6.7
Crew
8.7
Entertainment
6.7
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Food
6.7
Crew
8.7
Entertainment
6.7
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
La Mesa
Coronado
Santee
San Ysidro
Julian
Lemon Grove
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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 August 4, 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 August 4, 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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$173 | Average$384 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$517 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$283 | Average$455 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$295 | Average$575 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$336 | Average$506 | FlexibilityNo cancel fee | On-time63% |