$109+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Apr 15 — Apr 221
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Diego to Chesapeake are usually found in May or August, booked 62 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
Cheap flight deals from San Diego to Chesapeake
Cheapest
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 March 16, 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 March 16, 2026.
This Breeze Airways deal was found by Cheapflights users on 3/16. 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 5/221:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Mon 6/19:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 3/16![Breeze Airways logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 5/166:54 pm
SAN
- ORF
2 stops13h 17m
Multiple Airlines
Mon 5/189:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 5/131:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 5/1912:06 pm
ORF
- SAN
2 stops23h 36m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Fri 5/151:05 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 5/1912:06 pm
ORF
- SAN
3 stops30h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/11:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Sat 8/89:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 3/13![Breeze Airways logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:18 pm
SAN
- ORF
2 stops12h 53m
Multiple Airlines
Mon 5/189:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:54 pm
SAN
- ORF
1 stop22h 07m
Multiple Airlines
Sat 5/169:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$342
This Breeze Airways deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Wed 5/279:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 3/11![Breeze Airways logo]()
$348
This Priceline deal was found by Cheapflights users on 3/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:30 pm
SAN
- ORF
1 stop11h 02m
Multiple Airlines
Sat 5/99:51 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:20 am
SAN
- ORF
1 stop9h 40m
United Airlines
Wed 4/155:05 pm
ORF
- SAN
1 stop8h 54m
United Airlines
Deal found 3/12![United Airlines logo]()
$367
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 March 16, 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 March 16, 2026.
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:25 am
SAN
- ORF
1 stop7h 15m
Southwest
Mon 4/205:25 pm
ORF
- SAN
1 stop7h 35m
Southwest
Deal found 3/15![Southwest logo]()
$403
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:40 am
SAN
- ORF
1 stop7h 47m
United Airlines
Sat 6/205:39 pm
ORF
- SAN
1 stop9h 01m
United Airlines
Deal found 3/12![United Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:40 pm
SAN
- ORF
2 stops10h 15m
Southwest
Tue 4/1411:10 am
ORF
- SAN
2 stops10h 30m
Southwest
Deal found 3/14![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 4/249:35 pm
SAN
- ORF
2 stops10h 15m
Southwest
Mon 4/272:30 pm
ORF
- SAN
1 stop7h 30m
Southwest
Deal found 3/13![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:40 pm
SAN
- ORF
1 stop8h 45m
Southwest
Sat 4/181:15 pm
ORF
- SAN
2 stops9h 55m
Southwest
Deal found 3/15![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:40 pm
SAN
- ORF
2 stops10h 15m
Southwest
Mon 4/135:25 pm
ORF
- SAN
1 stop7h 35m
Southwest
Deal found 3/14![Southwest logo]()
$439
This Southwest deal was found by Cheapflights users on 3/11. 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 5/281:05 pm
SAN
- ORF
1 stop6h 50m
Southwest
Sun 5/316:05 pm
ORF
- SAN
1 stop7h 30m
Southwest
Deal found 3/11![Southwest logo]()
$463
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:40 pm
SAN
- ORF
1 stop7h 50m
Southwest
Sun 9/134:40 pm
ORF
- SAN
1 stop9h 05m
Southwest
Deal found 3/12![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sat 6/131:05 pm
SAN
- ORF
1 stop7h 00m
Southwest
Sat 6/205:40 pm
ORF
- SAN
1 stop7h 35m
Southwest
Deal found 3/14![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:00 pm
SAN
- ORF
2 stops9h 15m
Southwest
Mon 8/171:05 pm
ORF
- SAN
2 stops9h 15m
Southwest
Deal found 3/13![Southwest logo]()
$477
Last-minute flights from San Diego to ChesapeakeDiscover last-minute flight deals from San Diego to Chesapeake. Data last updated March 16, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chesapeake. Data last updated March 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Thu 4/29:02 pm
SAN
- ORF
1 stop20h 36m
Multiple Airlines
Sat 4/115:29 pm
ORF
- SAN
2 stops40h 52m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/43:46 pm
SAN
- ORF
1 stop25h 38m
Multiple Airlines
Sat 4/115:29 pm
ORF
- SAN
2 stops40h 52m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/43:46 pm
SAN
- ORF
1 stop25h 38m
Multiple Airlines
Fri 4/1011:33 am
ORF
- SAN
2 stops39h 29m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Sun 4/59:56 pm
SAN
- ORF
1 stop19h 42m
Multiple Airlines
Sat 4/115:29 pm
ORF
- SAN
2 stops40h 52m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/610:43 pm
SAN
- ORF
1 stop8h 09m
American Airlines
Wed 4/81:32 pm
ORF
- SAN
1 stop10h 18m
American Airlines
Deal found 3/12![American Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:20 am
SAN
- ORF
1 stop9h 40m
United Airlines
Wed 4/155:05 pm
ORF
- SAN
1 stop8h 54m
United Airlines
Deal found 3/12![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:45 pm
SAN
- ORF
1 stop9h 07m
American Airlines
Mon 4/205:30 pm
ORF
- SAN
1 stop8h 19m
American Airlines
Deal found 3/12![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:45 pm
SAN
- ORF
1 stop8h 14m
Delta
Tue 4/145:57 pm
ORF
- SAN
1 stop8h 58m
Delta
Deal found 3/13![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:40 pm
SAN
- ORF
2 stops10h 15m
Southwest
Tue 4/214:25 pm
ORF
- SAN
1 stop9h 00m
Southwest
Deal found 3/12![Southwest logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/167:23 pm
SAN
- ORF
2 stops11h 29m
Multiple Airlines
Thu 5/219:31 am
ORF
- SAN
1 stop30h 12m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$370
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 March 16, 2026.
Search for one-way flight options from San Diego to Chesapeake. Find affordable one-way fares based on user searches. Data last updated March 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/16![Breeze Airways logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Thu 5/71:38 pm
SAN
- ORF
2 stops18h 33m
Frontier
Deal found 3/14![Frontier logo]()
$131
This Booking.com deal was found by Cheapflights users on 3/11. 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.
Sat 6/131:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/11![Breeze Airways logo]()
$142
This Super.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/12![Breeze Airways logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 7/81:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/14![Breeze Airways logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
Breeze Airways
Deal found 3/11![Breeze Airways logo]()
$168
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:30 pm
SAN
- ORF
1 stop8h 51m
American Airlines
Deal found 3/12![American Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Mon 7/61:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/14![Breeze Airways logo]()
$188
This United Airlines deal was found by Cheapflights users on 3/11. 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 4/710:30 pm
SAN
- ORF
2 stops10h 24m
United Airlines
Deal found 3/11![United Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Mon 3/309:58 pm
SAN
- ORF
2 stops55h 11m
Frontier
Deal found 3/15![Frontier logo]()
$192
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 March 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (Breeze Airways) |
One-way from | $109 (Kiwi.com) |
Popular in | January |
Cheapest in | May |
Average price | $540 |
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 March 16, 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
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Sat 4/18
6:25 am-4:40 pm
1 stop7h 15m
Norfolk
Mon 4/20
5:25 pm-10:00 pm
1 stop7h 35m
$403
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 4/7
10:40 pm-11:55 am
2 stops10h 15m
Norfolk
Tue 4/14
11:10 am-6:40 pm
2 stops10h 30m
$413
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Fri 4/24
9:35 pm-10:50 am
2 stops10h 15m
Norfolk
Mon 4/27
2:30 pm-7:00 pm
1 stop7h 30m
$419
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 4/15
9:40 pm-9:25 am
1 stop8h 45m
Norfolk
Sat 4/18
1:15 pm-8:10 pm
2 stops9h 55m
$433
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 4/7
10:40 pm-11:55 am
2 stops10h 15m
Norfolk
Mon 4/13
5:25 pm-10:00 pm
1 stop7h 35m
$439
Quickest round-trip
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 5/28
1:05 pm-10:55 pm
1 stop6h 50m
Norfolk
Sun 5/31
6:05 pm-10:35 pm
1 stop7h 30m
$463
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Sat 6/13
6:40 am-5:27 pm
1 stop7h 47m
Norfolk
Sat 6/20
5:39 pm-11:40 pm
1 stop9h 01m
$467
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 9/10
10:40 pm-9:30 am
1 stop7h 50m
Norfolk
Sun 9/13
4:40 pm-10:45 pm
1 stop9h 05m
$467
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Sat 6/13
1:05 pm-11:05 pm
1 stop7h 00m
Norfolk
Sat 6/20
5:40 pm-10:15 pm
1 stop7h 35m
$477
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Mon 8/10
9:00 pm-9:15 am
2 stops9h 15m
Norfolk
Mon 8/17
1:05 pm-7:20 pm
2 stops9h 15m
$477
Showing 1-10 of 20 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
How far ahead should I book a flight from San Diego to Chesapeake?
Use this chart to determine the optimal time to book a round-trip flight from San Diego to Chesapeake. Price data was last updated on March 13, 2026.
Booking 62 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Diego to Chesapeake. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from San Diego to Chesapeake?
Currently, May is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $122). Flying from San Diego to Chesapeake in March is currently the most expensive (average of $312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 16, 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.
Crew
8.7
Food
6.6
Overall
8.1
Entertainment
6.6
Comfort
8.2
Boarding
8.3
Reviews
1 / 17
2.0
MediocreJustine,Jan 2026
RDU - MCO
Crew
8.7
Food
6.6
Overall
8.1
Entertainment
6.6
Comfort
8.2
Boarding
8.3
Reviews
1 / 17
2.0
MediocreJustine,Jan 2026
RDU - MCO
Crew
8.7
Food
6.6
Overall
8.1
Entertainment
6.6
Comfort
8.2
Boarding
8.3
Reviews
1 / 17
2.0
MediocreJustine,Jan 2026
RDU - MCO
Crew
8.7
Food
6.6
Overall
8.1
Entertainment
6.6
Comfort
8.2
Boarding
8.3
Reviews
1 / 17
2.0
MediocreJustine,Jan 2026
RDU - MCO
Crew
8.7
Food
6.6
Overall
8.1
Entertainment
6.6
Comfort
8.2
Boarding
8.3
Reviews
1 / 17
2.0
MediocreJustine,Jan 2026
RDU - MCO
Crew
8.7
Food
6.6
Overall
8.1
Entertainment
6.6
Comfort
8.2
Boarding
8.3
Reviews
1 / 17
2.0
MediocreJustine,Jan 2026
RDU - MCO
Related info for your journey
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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 March 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$361 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$422 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$206 | Average$453 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$308 | Average$452 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$325 | Average$504 | FlexibilityNo cancel fee | On-time71% |