$158+ Cheap flights from San Diego (SAN) to Chesapeake, VA
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from San Diego to Chesapeake with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Diego to Chesapeake are usually found in September or August, booked 62 days in advance, depart on a Wednesday or Tuesday and return on a Friday
Cheap flight deals from San Diego to Chesapeake
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Best
Last-minute
One-way
Cheapest flights from San Diego to ChesapeakeExplore the most affordable flight options available from San Diego to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
Explore the most affordable flight options available from San Diego to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Wed 9/212:21 pm
ORF
- SAN
2 stops23h 21m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$358
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:55 pm
SAN
- ORF
1 stop9h 34m
American Airlines
Tue 7/286:56 pm
ORF
- SAN
1 stop8h 03m
American Airlines
Deal found 6/15![American Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:35 am
SAN
- ORF
2 stops9h 15m
Southwest
Wed 9/24:35 pm
ORF
- SAN
1 stop8h 25m
Southwest
Deal found 6/14![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 8/123:03 pm
SAN
- ORF
3 stops17h 23m
Multiple Airlines
Sat 8/159:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$370
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.
Tue 8/410:40 pm
SAN
- ORF
1 stop10h 25m
Southwest
Tue 8/1112:15 pm
ORF
- SAN
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$374
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 9/261:13 pm
SAN
- ORF
Nonstop5h 06m
Multiple Airlines
Thu 10/112:57 pm
ORF
- SAN
2 stops22h 22m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:29 pm
SAN
- ORF
1 stop25h 44m
Breeze Airways
Wed 9/29:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 6/14![Breeze Airways logo]()
$376
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 7/208:51 pm
SAN
- ORF
2 stops20h 48m
Multiple Airlines
Mon 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$378
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 8/71:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Fri 8/1412:10 pm
ORF
- SAN
2 stops34h 56m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$380
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.
Fri 7/101:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 7/1412:10 pm
ORF
- SAN
2 stops14h 54m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$382
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.
Sat 7/46:15 am
SAN
- ORF
1 stop9h 55m
American Airlines
Wed 7/82:29 pm
ORF
- SAN
1 stop10h 16m
American Airlines
Deal found 6/16![American Airlines logo]()
$383
Best flights from San Diego to ChesapeakeDiscover carefully curated flight deals from San Diego to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
Discover carefully curated flight deals from San Diego to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
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.
Wed 8/192:00 pm
SAN
- ORF
1 stop8h 03m
Delta
Sun 8/236:00 am
ORF
- SAN
1 stop7h 20m
Delta
Deal found 6/17![Delta logo]()
$415
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.
Tue 8/49:35 am
SAN
- ORF
2 stops8h 55m
Southwest
Tue 8/1112:15 pm
ORF
- SAN
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$418
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:40 pm
SAN
- ORF
1 stop8h 03m
United Airlines
Wed 9/26:00 am
ORF
- SAN
1 stop8h 15m
United Airlines
Deal found 6/13![United Airlines logo]()
$473
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.
Tue 8/410:40 pm
SAN
- ORF
1 stop10h 25m
Southwest
Thu 8/61:05 pm
ORF
- SAN
2 stops9h 15m
Southwest
Deal found 6/15![Southwest logo]()
$426
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.
Sun 11/110:40 pm
SAN
- ORF
1 stop7h 24m
Delta
Thu 11/123:05 pm
ORF
- SAN
1 stop8h 13m
Delta
Deal found 6/17![Delta logo]()
$443
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:40 pm
SAN
- ORF
2 stops10h 00m
Southwest
Tue 7/287:00 pm
ORF
- SAN
1 stop7h 25m
Southwest
Deal found 6/13![Southwest logo]()
$430
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:55 pm
SAN
- ORF
2 stops11h 39m
United Airlines
Tue 9/85:02 pm
ORF
- SAN
1 stop8h 08m
United Airlines
Deal found 6/13![United Airlines logo]()
$478
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.
Fri 7/319:55 pm
SAN
- ORF
1 stop8h 20m
Southwest
Mon 8/37:15 pm
ORF
- SAN
1 stop7h 15m
Southwest
Deal found 6/15![Southwest logo]()
$439
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.
Tue 12/18:00 am
SAN
- ORF
2 stops10h 10m
Southwest
Thu 12/106:15 am
ORF
- SAN
2 stops10h 15m
Southwest
Deal found 6/17![Southwest logo]()
$446
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.
Fri 8/76:45 am
SAN
- ORF
1 stop12h 10m
Southwest
Fri 8/143:45 pm
ORF
- SAN
2 stops9h 15m
Southwest
Deal found 6/15![Southwest logo]()
$450
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.
Thu 8/209:25 am
SAN
- ORF
2 stops9h 10m
Southwest
Sun 8/233:15 pm
ORF
- SAN
2 stops10h 20m
Southwest
Deal found 6/15![Southwest logo]()
$453
Last-minute flights from San Diego to ChesapeakeDiscover last-minute flight deals from San Diego to Chesapeake. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chesapeake. Data last updated June 19, 2026 and is based on user searches.
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.
Sat 7/46:15 am
SAN
- ORF
1 stop9h 55m
American Airlines
Wed 7/82:29 pm
ORF
- SAN
1 stop10h 16m
American Airlines
Deal found 6/16![American Airlines logo]()
$383
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 7/41:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 7/712:10 pm
ORF
- SAN
2 stops28h 58m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$397
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.
Sat 7/47:50 am
SAN
- ORF
1 stop8h 55m
Southwest
Wed 7/812:25 pm
ORF
- SAN
2 stops10h 10m
Southwest
Deal found 6/16![Southwest logo]()
$416
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.
Fri 7/101:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 7/1412:10 pm
ORF
- SAN
2 stops14h 54m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$382
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 7/111:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 7/1412:10 pm
ORF
- SAN
2 stops14h 54m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$409
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 7/1410:40 pm
SAN
- ORF
2 stops10h 20m
Southwest
Tue 7/215:15 am
ORF
- SAN
2 stops10h 00m
Southwest
Deal found 6/16![Southwest logo]()
$401
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:55 pm
SAN
- ORF
1 stop9h 34m
American Airlines
Tue 7/286:56 pm
ORF
- SAN
1 stop8h 03m
American Airlines
Deal found 6/15![American Airlines logo]()
$363
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 7/156:15 am
SAN
- ORF
1 stop9h 01m
American Airlines
Sat 7/185:12 am
ORF
- SAN
1 stop6h 48m
American Airlines
Deal found 6/16![American Airlines logo]()
$415
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.
Sat 7/181:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Sat 7/259:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 6/18![Breeze Airways logo]()
$417
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 7/208:51 pm
SAN
- ORF
2 stops20h 48m
Multiple Airlines
Mon 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$378
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 7/311:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Sat 8/159:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 6/16![Breeze Airways logo]()
$398
One-way flights from San Diego to ChesapeakeSearch for one-way flight options from San Diego to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
Search for one-way flight options from San Diego to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 19, 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.
Wed 8/54:40 pm
SAN
- ORF
2 stops15h 35m
Frontier
Deal found 6/17![Frontier logo]()
$158
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 8/318:59 pm
SAN
- ORF
2 stops36h 26m
Frontier
Deal found 6/17![Frontier logo]()
$163
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.
Tue 7/73:03 pm
SAN
- ORF
2 stops17h 12m
Frontier
Deal found 6/16![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/143:03 pm
SAN
- ORF
2 stops26h 36m
Frontier
Deal found 6/13![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:51 pm
SAN
- ORF
2 stops44h 48m
Frontier
Deal found 6/13![Frontier logo]()
$177
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 7/146:15 am
SAN
- ORF
1 stop7h 37m
American Airlines
Deal found 6/16![American Airlines logo]()
$182
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/181:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/16![Breeze Airways 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.
Fri 7/171:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/18![Breeze Airways logo]()
$193
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/101:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/17![Breeze Airways logo]()
$194
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.
Thu 8/1310:10 am
SAN
- ORF
2 stops22h 05m
Frontier
Deal found 6/16![Frontier logo]()
$195
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:15 am
SAN
- ORF
1 stop9h 55m
American Airlines
Deal found 6/14![American Airlines logo]()
$202
This Super.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 6/14![Breeze Airways logo]()
$203
Find flight deals from San Diego to Chesapeake
Keep the following information in mind while searching for San Diego to Chesapeake flight deals. Data was last updated June 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $358 (Kiwi.com) |
One-way from | $158 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $467 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Chesapeake that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
Use the filters below to find and compare flights from San Diego to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 8/19
2:00 pm-1:03 am
1 stop8h 03m
Norfolk
Sun 8/23
6:00 am-10:20 am
1 stop7h 20m
$415
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 8/4
9:35 am-9:30 pm
2 stops8h 55m
Norfolk
Tue 8/11
12:15 pm-6:55 pm
2 stops9h 40m
$418
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 8/4
10:40 pm-12:05 pm
1 stop10h 25m
Norfolk
Thu 8/6
1:05 pm-7:20 pm
2 stops9h 15m
$426
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 7/23
10:40 pm-11:40 am
2 stops10h 00m
Norfolk
Tue 7/28
7:00 pm-11:25 pm
1 stop7h 25m
$430
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Fri 7/31
9:55 pm-9:15 am
1 stop8h 20m
Norfolk
Mon 8/3
7:15 pm-11:30 pm
1 stop7h 15m
$439
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Sun 11/1
10:40 pm-9:04 am
1 stop7h 24m
Norfolk
Thu 11/12
3:05 pm-8:18 pm
1 stop8h 13m
$443
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 12/1
8:00 am-9:10 pm
2 stops10h 10m
Norfolk
Thu 12/10
6:15 am-1:30 pm
2 stops10h 15m
$446
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Fri 8/7
6:45 am-9:55 pm
1 stop12h 10m
Norfolk
Fri 8/14
3:45 pm-10:00 pm
2 stops9h 15m
$450
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 8/20
9:25 am-9:35 pm
2 stops9h 10m
Norfolk
Sun 8/23
3:15 pm-10:35 pm
2 stops10h 20m
$453
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 9/1
12:40 pm-11:43 pm
1 stop8h 03m
Norfolk
Wed 9/2
6:00 am-11:15 am
1 stop8h 15m
$473
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from San Diego to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from San Diego with our price prediction graph.
SAN-ORF
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 San Diego to Chesapeake
SAN-C6E
SAN-ORF
What is the cheapest time of day to fly from SAN to C6E?
Find hourly flight availability from San Diego to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 19, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Diego to Chesapeake as you normally would.
How much does it cost to fly round-trip from San Diego to Chesapeake?
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chesapeake. Reviews last updated June 19, 2026.
Read reviews from past customers who have flown Breeze Airways,Southwest, andDelta from San Diego to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.6
Crew
8.8
Boarding
8.3
Overall
8.2
Comfort
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.6
Crew
8.8
Boarding
8.3
Overall
8.2
Comfort
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.6
Crew
8.8
Boarding
8.3
Overall
8.2
Comfort
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.6
Crew
8.8
Boarding
8.3
Overall
8.2
Comfort
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.6
Crew
8.8
Boarding
8.3
Overall
8.2
Comfort
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.6
Crew
8.8
Boarding
8.3
Overall
8.2
Comfort
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from San Diego to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for San Diego to Chesapeake
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Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Diego to Chesapeake by cabin class
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San Diego and Chesapeake flights
Browse other San Diego and Chesapeake flight options. Last updated on June 19, 2026.
Other flights from San Diego
Browse through other flights departing from San Diego. Flights are based on user searches made on Cheapflights and were last updated on June 19, 2026.
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San Diego to Chesapeake flights
Consider these flights traveling from San Diego to Chesapeake.
Top 7 airlines flying from San Diego to Chesapeake
Discover the top 7 airlines that operate flights from San Diego to Chesapeake. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$146 | Average$376 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$458 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$308 | Average$483 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$336 | Average$503 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$350 | Average$522 | FlexibilityNo cancel fee | On-time69% |