$113+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Jun 5 — Jun 121
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 August or September, booked 68 days in advance, depart on a Tuesday or Saturday and return on a Tuesday
Cheap flight deals from Chesapeake to San Diego
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Best
Last-minute
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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 May 6, 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 May 6, 2026.
This Breeze Airways deal was found by Cheapflights users on 5/3. 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
Mon 8/241:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/3![Breeze Airways logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/239:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 5/266:25 am
SAN
- ORF
2 stops49h 46m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Fri 8/149:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Wed 8/194:17 pm
SAN
- ORF
2 stops16h 09m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$290
This Gotogate deal was found by Cheapflights users on 5/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 5/161:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Thu 5/2812:06 pm
ORF
- SAN
2 stops33h 24m
Multiple Airlines
Mon 6/11:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 5/5. 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
Sat 10/101:13 pm
SAN
- ORF
Nonstop5h 06m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 8/1612:21 pm
ORF
- SAN
2 stops14h 37m
Multiple Airlines
Sat 8/221:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$299
This Gotogate deal was found by Cheapflights users on 5/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$304
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip 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
Wed 8/191:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$305
This Gotogate deal was found by Cheapflights users on 5/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Mon 6/11:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Fri 8/149:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 8/189:53 pm
SAN
- ORF
2 stops20h 08m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Fri 5/229:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 5/264:17 pm
SAN
- ORF
2 stops15h 54m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$317
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 May 6, 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 May 6, 2026.
This Delta deal was found by Cheapflights users on 5/4. 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 5/256:00 am
ORF
- SAN
1 stop7h 23m
Delta
Mon 6/11:50 pm
SAN
- ORF
1 stop7h 28m
Delta
Deal found 5/4![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:45 am
ORF
- SAN
2 stops9h 56m
United Airlines
Tue 6/911:58 am
SAN
- ORF
1 stop7h 32m
United Airlines
Deal found 5/3![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:15 pm
ORF
- SAN
1 stop7h 10m
Southwest
Sun 7/1910:40 pm
SAN
- ORF
1 stop13h 10m
Southwest
Deal found 5/6![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 5/5. 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 7/66:10 pm
ORF
- SAN
1 stop8h 10m
Southwest
Fri 7/106:35 am
SAN
- ORF
2 stops9h 00m
Southwest
Deal found 5/5![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 5/5. 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 7/206:10 pm
ORF
- SAN
1 stop8h 10m
Southwest
Mon 7/276:40 am
SAN
- ORF
2 stops8h 55m
Southwest
Deal found 5/5![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 5/4. 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 10/96:05 pm
ORF
- SAN
1 stop7h 58m
Delta
Sun 10/112:00 pm
SAN
- ORF
1 stop6h 59m
Delta
Deal found 5/4![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 5/5. 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 6/1212:15 pm
ORF
- SAN
2 stops9h 30m
Southwest
Mon 6/158:05 pm
SAN
- ORF
2 stops10h 20m
Southwest
Deal found 5/5![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 5/5. 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 9/234:35 pm
ORF
- SAN
1 stop8h 25m
Southwest
Sun 9/276:40 am
SAN
- ORF
1 stop8h 10m
Southwest
Deal found 5/5![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 5/5. 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.
Sun 8/165:05 pm
ORF
- SAN
2 stops9h 00m
Southwest
Sat 8/2210:40 pm
SAN
- ORF
2 stops10h 55m
Southwest
Deal found 5/5![Southwest logo]()
$448
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/254:30 pm
ORF
- SAN
1 stop9h 50m
Southwest
Sun 7/59:40 pm
SAN
- ORF
1 stop8h 40m
Southwest
Deal found 5/2![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 5/4. 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 10/93:55 pm
ORF
- SAN
1 stop10h 00m
Southwest
Mon 10/1210:40 pm
SAN
- ORF
2 stops9h 25m
Southwest
Deal found 5/4![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:15 pm
ORF
- SAN
1 stop8h 05m
Southwest
Sun 6/1410:40 pm
SAN
- ORF
2 stops10h 00m
Southwest
Deal found 5/2![Southwest logo]()
$472
Last-minute flights from Chesapeake to San DiegoDiscover last-minute flight deals from Chesapeake to San Diego. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to San Diego. Data last updated May 6, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 5/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 5/161:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$295
This Gotogate deal was found by Cheapflights users on 5/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Fri 5/229:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 5/264:17 pm
SAN
- ORF
2 stops15h 54m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/239:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Tue 5/266:25 am
SAN
- ORF
2 stops49h 46m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$284
This Gotogate deal was found by Cheapflights users on 5/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 5/301:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/249:31 am
ORF
- SAN
1 stop30h 12m
Multiple Airlines
Fri 5/291:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Thu 5/2812:06 pm
ORF
- SAN
2 stops33h 24m
Multiple Airlines
Mon 6/11:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$296
This Gotogate deal was found by Cheapflights users on 5/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Mon 6/11:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Fri 5/299:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Fri 6/56:25 am
SAN
- ORF
2 stops49h 46m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/1012:21 pm
ORF
- SAN
2 stops23h 27m
Multiple Airlines
Sat 6/201:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$318
This Gotogate deal was found by Cheapflights users on 5/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Sat 6/201:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$339
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 May 6, 2026.
Search for one-way flight options from Chesapeake to San Diego. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/2612:06 pm
ORF
- SAN
2 stops23h 36m
Frontier
Deal found 5/5![Frontier logo]()
$113
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/3112:06 pm
ORF
- SAN
2 stops38h 44m
Frontier
Deal found 5/5![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 6/612:00 pm
ORF
- SAN
2 stops14h 44m
Frontier
Deal found 5/2![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 7/412:06 pm
ORF
- SAN
2 stops30h 25m
Frontier
Deal found 5/5![Frontier logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 7/2012:21 pm
ORF
- SAN
2 stops38h 30m
Frontier
Deal found 5/5![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 7/112:21 pm
ORF
- SAN
2 stops23h 48m
Frontier
Deal found 5/5![Frontier logo]()
$167
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/2512:06 pm
ORF
- SAN
2 stops27h 03m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$170
This Mytrip deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/167:25 pm
ORF
- SAN
2 stops40h 23m
Frontier
Deal found 5/3![Frontier logo]()
$172
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Breeze Airways) |
One-way from | $113 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $378 |
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 May 6, 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
Mon 5/25
6:00 am-10:23 am
1 stop7h 23m
San Diego
Mon 6/1
1:50 pm-12:18 am
1 stop7h 28m
$359
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Tue 6/2
10:45 am-5:41 pm
2 stops9h 56m
San Diego
Tue 6/9
11:58 am-10:30 pm
1 stop7h 32m
$388
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 7/17
7:15 pm-11:25 pm
1 stop7h 10m
San Diego
Sun 7/19
10:40 pm-2:50 pm
1 stop13h 10m
$418
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 7/6
6:10 pm-11:20 pm
1 stop8h 10m
San Diego
Fri 7/10
6:35 am-6:35 pm
2 stops9h 00m
$418
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Mon 7/20
6:10 pm-11:20 pm
1 stop8h 10m
San Diego
Mon 7/27
6:40 am-6:35 pm
2 stops8h 55m
$418
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 6/12
12:15 pm-6:45 pm
2 stops9h 30m
San Diego
Mon 6/15
8:05 pm-9:25 am
2 stops10h 20m
$433
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Wed 9/23
4:35 pm-10:00 pm
1 stop8h 25m
San Diego
Sun 9/27
6:40 am-5:50 pm
1 stop8h 10m
$435
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Sun 8/16
5:05 pm-11:05 pm
2 stops9h 00m
San Diego
Sat 8/22
10:40 pm-12:35 pm
2 stops10h 55m
$448
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Fri 10/9
6:05 pm-11:03 pm
1 stop7h 58m
San Diego
Sun 10/11
2:00 pm-11:59 pm
1 stop6h 59m
$467
NorfolkSan Diego
ORF - SAN
ORFSAN
Norfolk
Thu 6/25
4:30 pm-11:20 pm
1 stop9h 50m
San Diego
Sun 7/5
9:40 pm-9:20 am
1 stop8h 40m
$467
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
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 May 6, 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
6.6
Comfort
8.2
Boarding
8.3
Crew
8.7
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Comfort
8.2
Boarding
8.3
Crew
8.7
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Comfort
8.2
Boarding
8.3
Crew
8.7
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Comfort
8.2
Boarding
8.3
Crew
8.7
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Comfort
8.2
Boarding
8.3
Crew
8.7
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Comfort
8.2
Boarding
8.3
Crew
8.7
Entertainment
6.6
Overall
8.1
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
Chula Vista
National City
Coronado
La Mesa
Poway
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 May 6, 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 May 6, 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$338 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$143 | Average$467 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$457 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$490 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$282 | Average$546 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$334 | Average$497 | FlexibilityNo cancel fee | On-time63% |