$124+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Jun 5 — Jun 121
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 August or September, 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 May 6, 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 May 6, 2026.
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Wed 5/2712:06 pm
ORF
- SAN
2 stops27h 37m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$236
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 6/212:06 pm
ORF
- SAN
2 stops38h 44m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$240
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Thu 5/2812:06 pm
ORF
- SAN
2 stops23h 36m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$255
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Sat 5/3012:00 pm
ORF
- SAN
2 stops27h 43m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$258
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 5/161:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Wed 8/199:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$268
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Sun 5/3112:06 pm
ORF
- SAN
3 stops38h 44m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$273
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Wed 5/279:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$277
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Sat 5/309:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$288
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 5/161:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Mon 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$292
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Mon 6/112:06 pm
ORF
- SAN
3 stops23h 36m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$293
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 8/239:53 pm
SAN
- ORF
2 stops34h 33m
Multiple Airlines
Mon 8/319:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$294
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.
Tue 5/269:37 am
SAN
- ORF
2 stops22h 34m
Multiple Airlines
Fri 5/299:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$295
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 May 6, 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 May 6, 2026.
This Breeze Airways 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 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 5/1![Breeze Airways logo]()
$318
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 7/106:35 am
SAN
- ORF
2 stops9h 00m
Southwest
Tue 7/214:30 pm
ORF
- SAN
2 stops9h 50m
Southwest
Deal found 5/4![Southwest logo]()
$423
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:05 pm
SAN
- ORF
1 stop9h 58m
United Airlines
Sat 5/306:00 am
ORF
- SAN
1 stop8h 21m
United Airlines
Deal found 5/2![United Airlines logo]()
$506
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.
Thu 6/256:30 am
SAN
- ORF
2 stops13h 55m
Southwest
Mon 6/294:30 pm
ORF
- SAN
1 stop9h 50m
Southwest
Deal found 5/4![Southwest logo]()
$424
This Breeze Airways 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 Breeze Airways 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
Breeze Airways
Mon 5/189:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/2![Breeze Airways logo]()
$428
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/221:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Sat 6/279:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/2![Breeze Airways logo]()
$448
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:45 pm
SAN
- ORF
1 stop8h 54m
United Airlines
Tue 6/210:45 am
ORF
- SAN
2 stops14h 54m
United Airlines
Deal found 5/4![United Airlines logo]()
$511
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.
Sat 6/139:40 pm
SAN
- ORF
2 stops10h 15m
Southwest
Sat 6/203:10 pm
ORF
- SAN
2 stops9h 35m
Southwest
Deal found 5/5![Southwest logo]()
$477
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:40 pm
SAN
- ORF
2 stops12h 37m
United Airlines
Thu 5/2810:45 am
ORF
- SAN
2 stops12h 06m
United Airlines
Deal found 5/4![United Airlines logo]()
$516
Last-minute flights from San Diego to ChesapeakeDiscover last-minute flight deals from San Diego to Chesapeake. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chesapeake. Data last updated May 6, 2026 and is based on user searches.
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 5/161:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Wed 8/199:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$268
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 5/161:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Mon 8/179:38 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$292
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Wed 5/2712:06 pm
ORF
- SAN
2 stops27h 37m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$236
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Tue 6/212:06 pm
ORF
- SAN
2 stops38h 44m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$240
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Thu 5/2812:06 pm
ORF
- SAN
2 stops23h 36m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$255
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Sat 5/3012:00 pm
ORF
- SAN
2 stops27h 43m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$258
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Sun 5/3112:06 pm
ORF
- SAN
3 stops38h 44m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$273
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Wed 5/279:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$277
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Sat 5/309:51 am
ORF
- SAN
Nonstop5h 42m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$288
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 5/231:22 pm
SAN
- ORF
Nonstop5h 23m
Multiple Airlines
Mon 6/112:06 pm
ORF
- SAN
3 stops23h 36m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$293
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.
Tue 5/269:37 am
SAN
- ORF
2 stops22h 34m
Multiple Airlines
Fri 5/299:38 am
ORF
- SAN
Nonstop5h 42m
Multiple Airlines
Deal found 5/4![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 May 6, 2026.
Search for one-way flight options from San Diego to Chesapeake. 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 5/266:25 am
SAN
- ORF
2 stops25h 46m
Frontier
Deal found 5/5![Frontier logo]()
$124
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 6/34:17 pm
SAN
- ORF
2 stops15h 54m
Frontier
Deal found 5/4![Frontier logo]()
$129
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 6/106:25 am
SAN
- ORF
2 stops26h 01m
Frontier
Deal found 5/4![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 6/2210:04 am
SAN
- ORF
2 stops46h 22m
Frontier
Deal found 5/5![Frontier logo]()
$160
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:46 am
SAN
- ORF
2 stops22h 40m
Frontier
Deal found 5/6![Frontier logo]()
$161
This Super.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 Super.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
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$168
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:37 am
SAN
- ORF
2 stops22h 38m
Frontier
Deal found 5/6![Frontier logo]()
$174
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 5/119:59 pm
SAN
- ORF
2 stops32h 07m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$175
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 5/151:05 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$178
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:22 pm
SAN
- ORF
Nonstop5h 23m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$179
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.
Wed 6/312:41 pm
SAN
- ORF
1 stop8h 37m
Delta
Deal found 5/4![Delta logo]()
$180
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $236 (Kiwi.com) |
One-way from | $124 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $342 |
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 May 6, 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
Sat 5/23
1:22 pm-9:45 pm
Nonstop5h 23m
Norfolk
Wed 5/27
9:51 am-12:33 pm
Nonstop5h 42m
$318
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Fri 7/10
6:35 am-6:35 pm
2 stops9h 00m
Norfolk
Tue 7/21
4:30 pm-11:20 pm
2 stops9h 50m
$423
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 6/25
6:30 am-11:25 pm
2 stops13h 55m
Norfolk
Mon 6/29
4:30 pm-11:20 pm
1 stop9h 50m
$424
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Fri 5/15
1:05 pm-9:28 pm
Nonstop5h 23m
Norfolk
Mon 5/18
9:38 am-12:20 pm
Nonstop5h 42m
$428
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Mon 6/22
1:05 pm-9:28 pm
Nonstop5h 23m
Norfolk
Sat 6/27
9:51 am-12:33 pm
Nonstop5h 42m
$448
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Sat 6/13
9:40 pm-10:55 am
2 stops10h 15m
Norfolk
Sat 6/20
3:10 pm-9:45 pm
2 stops9h 35m
$477
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Wed 5/27
9:05 pm-10:03 am
1 stop9h 58m
Norfolk
Sat 5/30
6:00 am-11:21 am
1 stop8h 21m
$506
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Thu 5/28
9:45 pm-9:39 am
1 stop8h 54m
Norfolk
Tue 6/2
10:45 am-10:39 pm
2 stops14h 54m
$511
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Tue 5/26
10:40 pm-2:17 pm
2 stops12h 37m
Norfolk
Thu 5/28
10:45 am-7:51 pm
2 stops12h 06m
$516
Cheapest one-way
San DiegoNorfolk
SAN - ORF
SANORF
San Diego
Mon 6/22
10:40 pm-11:05 am
1 stop9h 25m
$180
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 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 May 6, 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.
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Crew
8.7
Food
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Crew
8.7
Food
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Crew
8.7
Food
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Crew
8.7
Food
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Crew
8.7
Food
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Crew
8.7
Food
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 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
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San Diego and Chesapeake flights
Browse other San Diego and Chesapeake flight options. Last updated on May 6, 2026.
Other flights from San Diego
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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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$324 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$361 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$451 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$206 | Average$461 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$300 | Average$479 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$325 | Average$510 | FlexibilityNo cancel fee | On-time71% |