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$111+ Cheap flights from Chesapeake, VA to San Diego (SAN)

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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San Diego are usually found in August or May, booked 68 days in advance, depart on a Tuesday or Friday and return on a Tuesday

Cheap flight deals from Chesapeake to San Diego

Cheapest flights from Chesapeake to San Diego
Explore the most affordable flight options available from Chesapeake to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

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.
Thu 2/199:33 am
ORF
-
SAN
1 stop11h 18m
Multiple Airlines
Thu 2/262:38 pm
SAN
-
ORF
2 stops16h 59m
Multiple Airlines
Deal found 1/26$340
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.
Thu 5/79:16 am
ORF
-
SAN
1 stop8h 09m
Multiple Airlines
Mon 5/116:55 am
SAN
-
ORF
2 stops13h 04m
Multiple Airlines
Deal found 1/27$345
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.
Sun 2/159:33 am
ORF
-
SAN
1 stop12h 52m
Multiple Airlines
Sat 2/2111:21 am
SAN
-
ORF
2 stops20h 16m
Multiple Airlines
Deal found 1/28$349
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 2/199:33 am
ORF
-
SAN
1 stop11h 18m
Multiple Airlines
Mon 2/238:20 pm
SAN
-
ORF
2 stops12h 45m
Multiple Airlines
Deal found 1/28$352
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.
Tue 2/107:33 pm
ORF
-
SAN
2 stops25h 18m
Multiple Airlines
Thu 2/196:25 am
SAN
-
ORF
1 stop10h 59m
Multiple Airlines
Deal found 1/28$353
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.
Sat 4/256:05 am
ORF
-
SAN
3 stops20h 01m
Multiple Airlines
Sat 5/161:22 pm
SAN
-
ORF
Nonstop5h 23m
Multiple Airlines
Deal found 1/26$354
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:30 am
ORF
-
SAN
1 stop10h 50m
Southwest
Mon 3/29:45 pm
SAN
-
ORF
1 stop8h 55m
Southwest
Deal found 1/28$359
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.
Sat 5/96:05 am
ORF
-
SAN
3 stops20h 01m
Multiple Airlines
Fri 5/1512:55 pm
SAN
-
ORF
Nonstop5h 23m
Multiple Airlines
Deal found 1/27$362
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:23 am
ORF
-
SAN
1 stop8h 18m
United Airlines
Tue 3/312:55 pm
SAN
-
ORF
1 stop7h 04m
United Airlines
Deal found 1/27$363
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:55 am
ORF
-
SAN
2 stops10h 10m
Southwest
Tue 3/109:40 pm
SAN
-
ORF
1 stop8h 35m
Southwest
Deal found 1/28$364
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/174:40 pm
ORF
-
SAN
1 stop7h 50m
Southwest
Tue 2/2410:05 am
SAN
-
ORF
1 stop7h 25m
Southwest
Deal found 1/26$367

Find flight deals from Chesapeake to San Diego

Keep the following information in mind while searching for Chesapeake to San Diego flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$340
(Kiwi.com)

One-way from

$111
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$476
Provider with most accurate pricing for Norfolk-San Diego flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-San Diego flights.
Search Deals
From Chesapeake to San Diego
Search Deals
One-way flight from Chesapeake to San Diego
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 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 Chesapeake to San Diego 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 Chesapeake to San Diego that are best for you.

Fly from

Chesapeake

Fly to

San Diego

Route

Depart

Return

Price

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Thu 2/19

9:33 am-10:19 pm

1 stop15h 46m

San Diego

Thu 2/26

6:25 am-8:24 pm

1 stop10h 59m

$351

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Thu 3/5

5:20 pm-11:25 pm

1 stop9h 05m

San Diego

Tue 3/10

9:40 pm-9:15 am

1 stop8h 35m

$359

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 2/25

5:35 pm-10:20 pm

1 stop7h 45m

San Diego

Sat 2/28

11:20 am-9:05 pm

1 stop6h 45m

$363

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 3/11

4:30 pm-10:05 pm

1 stop8h 35m

San Diego

Tue 3/17

9:40 pm-9:15 am

1 stop8h 35m

$363

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 3/2

5:45 am-12:50 pm

2 stops10h 05m

San Diego

Tue 3/10

9:40 pm-9:15 am

1 stop8h 35m

$364

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 2/27

3:05 pm-8:20 pm

1 stop8h 15m

San Diego

Mon 3/2

6:45 am-6:25 pm

2 stops8h 40m

$364

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 3/25

4:30 pm-10:05 pm

1 stop8h 35m

San Diego

Tue 3/31

12:45 pm-10:35 pm

1 stop6h 50m

$367

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 2/18

3:30 pm-10:48 pm

1 stop10h 18m

San Diego

Thu 2/26

6:15 am-5:17 pm

1 stop8h 02m

$368

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Tue 3/10

5:05 pm-11:05 pm

1 stop9h 00m

San Diego

Tue 3/17

9:45 am-10:35 pm

2 stops9h 50m

$368

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Thu 2/26

6:00 am-12:29 pm

1 stop9h 29m

San Diego

Sun 3/1

10:15 pm-9:48 am

1 stop8h 33m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chesapeake to San Diego

Have a flexible travel schedule? Discover the best time to fly to San Diego from Chesapeake 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 Chesapeake to San Diego

How far ahead should I book a flight from Chesapeake to San Diego?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to San Diego. Price data was last updated on January 23, 2026.

The price you pay for your flight from Chesapeake to San Diego may vary depending on when you book. For the best chance of a lower fare, look to book 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chesapeake to San Diego?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $127). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $300). 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 San Diego

Get insights into the airlines that provide service to San Diego. 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 San Diego. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and Delta from Chesapeake to San Diego by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.2

Crew

8.7

Entertainment

6.6

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

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.2

Crew

8.7

Entertainment

6.6

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

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.2

Crew

8.7

Entertainment

6.6

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

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.2

Crew

8.7

Entertainment

6.6

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

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.2

Crew

8.7

Entertainment

6.6

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

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.2

Crew

8.7

Entertainment

6.6

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 Chesapeake to San Diego. 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 into for flights to San Diego from Chesapeake?

    If you book a flight to San Diego from Chesapeake, you will be flying to San Diego, which is the city’s only airport. San Diego (SAN) is located 2.6 mi from the center of San Diego. There are 0 flights from Chesapeake to San Diego per day from 8 different airlines.

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

    There are many flights that can get you from Chesapeake to San Diego in 9h 05m. Fly via Southwest to get the fastest option. There are 2324 mi between Chesapeake and San Diego.

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

    To fly one-way, consider booking your trip with Breeze Airways, which is currently one of the cheapest options available, starting at $96. Southwest flights start at $148 while deals on American Airlines start at $155 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to San Diego 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 Chesapeake to San Diego?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $127). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $300). 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

Traveling to a place near San Diego?

Book flights to San Diego if you plan to visit one of these locations
El Cajon
Chula Vista
National City
Coronado
La Mesa
Poway
Julian
Lemon Grove

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chesapeake to San Diego

Discover the top 8 airlines that operate flights from Chesapeake to San Diego. 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
Spirit AirlinesCheapest$127Average$209FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$134Average$338FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$448FlexibilityNo cancel feeOn-time62%
FrontierCheapest$178Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$444FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$276Average$515FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$538FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$478FlexibilityNo cancel feeOn-time63%

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