$129+ Cheap flights from San Diego (SAN) to Chesapeake, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Oct 22 — Oct 291
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 May or September, booked 87 days in advance, depart on a Wednesday or Thursday and return on a Thursday
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 September 22, 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 September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:01 pm -
3 stops43h 37m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:44 pm -
2 stops15h 50m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 11/47:33 pm -
1 stop21h 53m
Tue 11/109:38 am -
1 stop27h 33m
Deal found 9/21![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/212:01 pm -
1 stop27h 20m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/21![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:01 pm -
3 stops43h 37m
Sat 10/319:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:44 pm -
2 stops15h 50m
Sat 10/319:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop27h 20m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop27h 20m
Tue 10/279:33 am -
1 stop27h 38m
Deal found 9/20![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop27h 20m
Sat 10/319:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/1712:38 pm -
1 stop8h 28m
Wed 10/215:25 pm -
1 stop9h 21m
Deal found 9/17![Delta logo]()
$305
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 September 22, 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 September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/169:50 pm -
1 stop9h 20m
Mon 10/195:50 pm -
1 stop9h 45m
Deal found 9/17![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:19 pm -
1 stop8h 39m
Tue 12/155:30 am -
1 stop9h 24m
Deal found 9/19![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/21. 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 12/312:39 pm -
1 stop7h 20m
Tue 12/1512:15 pm -
2 stops15h 04m
Deal found 9/21![United Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:45 pm -
2 stops10h 25m
Fri 12/114:35 pm -
1 stop8h 40m
Deal found 9/20![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/152:10 pm -
1 stop7h 35m
Tue 10/207:00 am -
1 stop7h 13m
Deal found 9/17![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 9/21. 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 10/2510:40 pm -
1 stop9h 20m
Tue 11/103:05 pm -
2 stops9h 50m
Deal found 9/21![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:32 am -
1 stop11h 05m
Wed 11/255:10 pm -
1 stop9h 49m
Deal found 9/18![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:05 pm -
2 stops10h 05m
Tue 12/86:15 am -
2 stops10h 15m
Deal found 9/18![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:23 pm -
2 stops12h 50m
Tue 12/1512:15 pm -
2 stops15h 04m
Deal found 9/20![United Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:20 am -
2 stops9h 20m
Sun 11/15:55 pm -
2 stops8h 55m
Deal found 9/18![Southwest logo]()
$424
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:20 am -
2 stops13h 56m
Wed 11/2511:45 am -
2 stops11h 39m
Deal found 9/18![United Airlines logo]()
$538
Last-minute flights from San Diego to ChesapeakeDiscover last-minute flight deals from San Diego to Chesapeake. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chesapeake. Data last updated September 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/1712:38 pm -
1 stop8h 28m
Sat 10/247:00 am -
1 stop8h 44m
Deal found 9/17![Delta logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop27h 20m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop27h 20m
Tue 10/279:33 am -
1 stop27h 38m
Deal found 9/20![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:01 pm -
1 stop27h 20m
Sat 10/319:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:01 pm -
3 stops43h 37m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:01 pm -
3 stops43h 37m
Sat 10/319:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/212:01 pm -
1 stop27h 20m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/21![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:44 pm -
2 stops15h 50m
Wed 10/289:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:44 pm -
2 stops15h 50m
Sat 10/319:22 am -
Nonstop6h 06m
Deal found 9/20![Multiple Airlines logo]()
$295
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 September 22, 2026.
Search for one-way flight options from San Diego to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:13 pm -
Nonstop5h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Breeze Airways logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/133:09 pm -
1 stop26h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:13 pm -
Nonstop5h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Breeze Airways logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/212:01 pm -
1 stop27h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$151
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:25 pm -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:24 am -
2 stops31h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$159
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:30 pm -
1 stop9h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$160
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 10/196:50 pm -
2 stops11h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:25 am -
2 stops27h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$168
This Delta deal was found by Cheapflights users on 9/22. 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 12/111:19 pm -
1 stop8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/121:13 pm -
Nonstop5h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Breeze Airways logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 1/163:09 pm -
1 stop26h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$179
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Kiwi.com) |
One-way from | $129 (Kiwi.com) |
Popular in | April |
Cheapest in | May |
Average price | $401 |
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 7,457,451 searches. Data last updated September 22, 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 San Diego - ORF Norfolk
SANORF
San Diego
Thu 12/10
6:35 am-5:25 pm
1 stop7h 50m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$160
Quickest round-trip
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Sat 11/14
6:20 am-4:14 pm
1 stop6h 54m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$160
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Wed 10/21
9:45 am-11:44 pm
2 stops10h 59m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$165
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Sat 11/14
11:21 am-11:44 pm
2 stops9h 23m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$165
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Fri 10/16
10:05 pm-11:22 am
1 stop10h 17m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$175
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Fri 12/11
1:19 pm-12:58 am
1 stop8h 39m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$175
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Sat 10/17
5:44 pm-12:34 pm
2 stops15h 50m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$185
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Fri 10/16
9:45 am-11:44 pm
2 stops10h 59m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$204
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Tue 10/6
6:28 pm-12:15 pm
2 stops14h 47m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$213
San DiegoNorfolk
SAN San Diego - ORF Norfolk
SANORF
San Diego
Thu 10/22
8:34 pm-2:55 pm
2 stops39h 21m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
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 September 22, 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?
Airfare is below average for this route at the moment.
San Diego to Chesapeake flights typically cost between $350 and $476 in October.The cheapest round-trip price found within the last 5 days was $287 on Multiple Airlines (Oct 20-Oct 28).
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 September 22, 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.
Food
6.8
Comfort
8.2
Overall
8.2
Crew
8.8
Entertainment
6.8
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Comfort
8.2
Overall
8.2
Crew
8.8
Entertainment
6.8
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Comfort
8.2
Overall
8.2
Crew
8.8
Entertainment
6.8
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Comfort
8.2
Overall
8.2
Crew
8.8
Entertainment
6.8
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Comfort
8.2
Overall
8.2
Crew
8.8
Entertainment
6.8
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Comfort
8.2
Overall
8.2
Crew
8.8
Entertainment
6.8
Boarding
8.4
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
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San Diego and Chesapeake flights
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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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$146 | Average$417 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$196 | Average$346 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$201 | Average$398 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$219 | Average$487 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$310 | Average$517 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$310 | Average$480 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$350 | Average$482 | FlexibilityNo cancel fee | On-time69% |