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Chesapeake

$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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chesapeake are usually found in August or May, 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 flights from San Diego to Chesapeake
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 January 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:05 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Mon 5/119:38 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Deal found 1/27$242
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/1512:55 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Mon 5/189:28 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Deal found 1/28$246
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 5/1512:55 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Fri 5/299:28 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Deal found 1/26$266
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/126:25 am
SAN
-
ORF
1 stop10h 59m
Multiple Airlines
Mon 2/1611:39 am
ORF
-
SAN
2 stops37h 02m
Multiple Airlines
Deal found 1/28$279
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 5/156:55 am
SAN
-
ORF
2 stops33h 34m
Multiple Airlines
Fri 5/299:28 am
ORF
-
SAN
Nonstop5h 42m
Multiple Airlines
Deal found 1/26$302
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/2212:55 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Fri 5/299:28 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Deal found 1/28$316
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/232:05 pm
SAN
-
ORF
2 stops19h 00m
Multiple Airlines
Sun 3/19:33 am
ORF
-
SAN
1 stop12h 52m
Multiple Airlines
Deal found 1/26$324
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/119:45 am
SAN
-
ORF
2 stops29h 41m
Multiple Airlines
Thu 2/199:33 am
ORF
-
SAN
1 stop15h 46m
Multiple Airlines
Deal found 1/28$329
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 5/812:55 pm
SAN
-
ORF
Nonstop5h 23m
Multiple Airlines
Mon 5/116:05 am
ORF
-
SAN
3 stops21h 06m
Multiple Airlines
Deal found 1/27$341
This Breeze Airways deal was found by Cheapflights users on 1/28. 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 6/121:05 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Fri 6/199:38 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Deal found 1/28$348
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/252:08 pm
SAN
-
ORF
2 stops17h 07m
Multiple Airlines
Mon 3/309:23 am
ORF
-
SAN
1 stop9h 50m
Multiple Airlines
Deal found 1/28$353
This Breeze Airways deal was found by Cheapflights users on 1/26. 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 7/2012:55 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Fri 7/249:28 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Deal found 1/26$358

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Mytrip)

One-way from

$109
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$478
Provider with most accurate pricing for San Diego-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Diego-Norfolk flights.
Search Deals
From San Diego to Chesapeake
Search Deals
One-way flight from San Diego to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
Use the filters below to find and compare flights from San Diego to Chesapeake that are best for you.

Fly from

San Diego

Fly to

Chesapeake

Route

Depart

Return

Price

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 3/5

9:40 pm-9:15 am

1 stop8h 35m

Norfolk

Tue 3/10

6:00 am-11:05 am

1 stop8h 05m

$359

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 2/25

9:45 pm-9:20 am

1 stop8h 35m

Norfolk

Wed 3/4

5:35 pm-10:20 pm

1 stop7h 45m

$359

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Tue 3/10

10:50 am-9:05 pm

1 stop7h 15m

Norfolk

Wed 3/25

5:05 pm-11:05 pm

1 stop9h 00m

$363

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 2/27

6:45 am-5:15 pm

1 stop7h 30m

Norfolk

Mon 3/2

5:45 am-12:50 pm

2 stops10h 05m

$364

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 3/6

9:40 pm-9:15 am

1 stop8h 35m

Norfolk

Sun 3/8

5:50 pm-10:45 pm

1 stop7h 55m

$379

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Tue 3/24

12:45 pm-10:35 pm

1 stop6h 50m

Norfolk

Mon 3/30

5:10 pm-11:25 pm

1 stop9h 15m

$380

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 2/28

12:23 pm-10:37 am

2 stops19h 14m

$109

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 3/11

8:25 am-10:15 am

2 stops22h 50m

$115

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 3/11

8:25 am-7:46 pm

3 stops32h 21m

$145

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 2/25

7:11 am-12:37 pm

3 stops26h 26m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 17 results
1
2

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.
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

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 January 23, 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 January is currently the most expensive (average of $307). 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 January 29, 2026.
Read reviews from past customers who have flown Breeze Airways, Southwest, and Delta 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.
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

Overall

8.2

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

Overall

8.2

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,267 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

Overall

8.2

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,127 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

Overall

8.2

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
United Airlines
7.4
Good
9,215 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

Overall

8.2

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,206 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

Overall

8.2

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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.

  • What airport do you fly from for flights from San Diego to Chesapeake?

    For a flight from San Diego to Chesapeake, you will be flying from San Diego. San Diego (SAN) is just 2.6 mi from the center of the city. San Diego is the only San Diego airport and it handles 0 outbound flights to Chesapeake per day. 7 airlines have flights to Chesapeake from San Diego on a regular basis.

  • How long is the flight from San Diego to Chesapeake?

    Southwest can get you from San Diego to Chesapeake in just under 8h 35m. Your travel time can differ by up to . The distance from San Diego to Chesapeake is about 2324 mi.

  • What are the cheapest airlines to fly from San Diego to Chesapeake one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $99. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from San Diego to Chesapeake for a low price.

  • Can I find deals for flights from San Diego to Chesapeake that include hotel bookings?

    Yes. In addition to deals on San Diego to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Chesapeake.

  • Can I find deals for business class flights from San Diego to Chesapeake?

    Yes. Cheapflights offers flight deals from San Diego to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 January is currently the most expensive (average of $307). 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.

See more FAQs

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$122Average$314FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$146Average$355FlexibilityNo cancel feeOn-time62%
DeltaCheapest$175Average$444FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$196Average$286FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$206Average$468FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$308Average$469FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$325Average$488FlexibilityNo cancel feeOn-time71%

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