HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Diego

$118+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to San Diego 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 Chesapeake to San Diego are usually found in August or September, 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 March 17, 2026.

This Priceline deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:38 am
ORF
-
SAN
Nonstop5h 42m
Multiple Airlines
Mon 5/188:30 pm
SAN
-
ORF
1 stop11h 02m
Multiple Airlines
Deal found 3/13$372
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:38 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Mon 6/151:05 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/13$376
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:30 pm
ORF
-
SAN
1 stop8h 19m
American Airlines
Mon 4/139:45 pm
SAN
-
ORF
1 stop9h 07m
American Airlines
Deal found 3/12$378
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:33 am
ORF
-
SAN
1 stop11h 56m
Multiple Airlines
Wed 5/67:34 pm
SAN
-
ORF
2 stops12h 37m
Multiple Airlines
Deal found 3/16$380
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:25 pm
ORF
-
SAN
1 stop9h 00m
Southwest
Mon 4/1310:40 pm
SAN
-
ORF
2 stops10h 15m
Southwest
Deal found 3/12$383
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:38 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Tue 6/212:54 pm
SAN
-
ORF
2 stops17h 14m
Breeze Airways
Deal found 3/16$384
This Breeze Airways deal was found by Cheapflights users on 3/17. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:38 am
ORF
-
SAN
Nonstop5h 42m
Breeze Airways
Wed 6/101:22 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/17$388
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:00 pm
ORF
-
SAN
1 stop7h 25m
Southwest
Tue 4/289:40 pm
SAN
-
ORF
1 stop9h 20m
Southwest
Deal found 3/16$390
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:30 pm
ORF
-
SAN
2 stops16h 09m
Breeze Airways
Sat 6/61:22 pm
SAN
-
ORF
Nonstop5h 23m
Breeze Airways
Deal found 3/17$391
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:25 pm
ORF
-
SAN
1 stop9h 00m
Southwest
Fri 4/249:40 pm
SAN
-
ORF
1 stop9h 10m
Southwest
Deal found 3/12$393
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:12 pm
ORF
-
SAN
3 stops27h 00m
Multiple Airlines
Sat 6/61:22 pm
SAN
-
ORF
Nonstop5h 23m
Multiple Airlines
Deal found 3/13$394

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$372
(Priceline)

One-way from

$118
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$514
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. 12% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 17, 2026.
Use the filters below to find and compare flights from Chesapeake to San Diego that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 6/1

9:38 am-12:20 pm

Nonstop5h 42m

San Diego

Wed 6/10

1:22 pm-9:45 pm

Nonstop5h 23m

$388

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 4/27

2:30 pm-10:00 pm

1 stop10h 30m

San Diego

Wed 4/29

8:40 am-9:10 pm

2 stops9h 30m

$408

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 5/1

2:30 pm-7:00 pm

1 stop7h 30m

San Diego

Tue 5/5

8:30 am-9:10 pm

1 stop9h 40m

$408

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sat 4/25

6:10 am-2:05 pm

2 stops10h 55m

San Diego

Mon 5/4

10:40 pm-11:55 am

2 stops10h 15m

$444

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 7/24

8:00 am-3:27 pm

1 stop10h 27m

San Diego

Fri 7/31

1:53 pm-12:41 am

1 stop7h 48m

$467

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 7/24

12:15 pm-6:45 pm

2 stops9h 30m

San Diego

Fri 7/31

9:55 pm-9:15 am

1 stop8h 20m

$472

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 6/22

4:30 pm-11:20 pm

1 stop9h 50m

San Diego

Sun 6/28

10:40 pm-10:45 am

1 stop9h 05m

$477

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sat 4/11

1:15 pm-8:10 pm

2 stops9h 55m

San Diego

Fri 4/17

9:35 pm-10:50 am

2 stops10h 15m

$493

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 6/17

7:00 pm-11:20 pm

1 stop7h 20m

San Diego

Mon 6/22

10:40 pm-10:45 am

1 stop9h 05m

$502

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 5/22

2:30 pm-9:25 pm

2 stops9h 55m

San Diego

Tue 6/2

10:40 pm-11:55 am

2 stops10h 15m

$508

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 March 13, 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 $102). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $318). 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 March 17, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andDelta 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
8.1
Very good
271 reviews

Entertainment

6.6

Comfort

8.2

Overall

8.1

Crew

8.7

Food

6.6

Boarding

8.3

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
8.1
Very good
271 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Comfort

8.2

Overall

8.1

Crew

8.7

Food

6.6

Boarding

8.3

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
4,320 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Comfort

8.2

Overall

8.1

Crew

8.7

Food

6.6

Boarding

8.3

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
8,288 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Comfort

8.2

Overall

8.1

Crew

8.7

Food

6.6

Boarding

8.3

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
9,431 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Comfort

8.2

Overall

8.1

Crew

8.7

Food

6.6

Boarding

8.3

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
7.1
Good
11,466 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Comfort

8.2

Overall

8.1

Crew

8.7

Food

6.6

Boarding

8.3

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 7 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 5h 42m. Fly via Breeze Airways or Southwest to get the fastest option. There are 2324 mi between Chesapeake and San Diego. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Delta start at $150 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 $102). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $318). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to San Diego

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Las Vegas flights
Dulles Intl to Los Angeles flights
Reagan-National to Los Angeles flights
Reagan-National to Las Vegas flights
Dulles Intl to San Francisco flights
Reagan-National to San Francisco flights
Raleigh to Las Vegas flights
Dulles Intl to San Diego flights
Reagan-National to San Diego flights
Raleigh to Los Angeles flights
Dulles Intl to Ontario flights
Raleigh to San Francisco flights
Reagan-National to Ontario flights
Richmond to Las Vegas flights
Dulles Intl to Sacramento flights
Dulles Intl to San Jose flights
Norfolk to Las Vegas flights
Reagan-National to San Jose flights
Dulles Intl to Oakland flights
Dulles Intl to Palm Springs flights
Greensboro to Las Vegas flights
Reagan-National to Oakland flights
Raleigh to Ontario flights
Reagan-National to Santa Ana flights
Raleigh to San Diego flights
Richmond to Los Angeles flights
Dulles Intl to Reno flights
Dulles Intl to Burbank flights
Roanoke to Las Vegas flights
Reagan-National to Palm Springs flights
Richmond to San Francisco flights
Reagan-National to Sacramento flights
Richmond to San Diego flights
Greensboro to Los Angeles flights
Dulles Intl to Santa Barbara flights
Reagan-National to Reno flights
Raleigh to San Jose flights
Raleigh to Santa Ana flights
Norfolk to Los Angeles flights
Reagan-National to Santa Barbara flights
Norfolk to San Diego flights
Raleigh to Oakland flights
Greensboro to San Francisco flights
Norfolk to San Francisco flights
Dulles Intl to Long Beach flights
Raleigh to Reno flights
Greensboro to San Diego flights
Richmond to Ontario flights

Top 7 airlines flying from Chesapeake to San Diego

Discover the top 7 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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$134Average$337FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$448FlexibilityNo cancel feeOn-time62%
DeltaCheapest$175Average$439FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$178Average$288FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$276Average$500FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$540FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$316Average$482FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.