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Chesapeake

$125+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
1 adult, Economy
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The best prices from San Diego to Chesapeake are usually found in September or August, booked 83 days in advance, depart on a Tuesday or Sunday and return on a Sunday

Cheap 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 March 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Booking.com)

One-way from

$125
(FlightHub)

Popular in

February

Cheapest in

September

Average price

$479
Provider with most accurate pricing for San Diego-Norfolk flight deals.
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Provider most trusted by Cheapflights users for San Diego-Norfolk flights.
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From San Diego to Chesapeake
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One-way flight from San Diego to Chesapeake
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Highest demand for flights based on searches. 19% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find 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 March 3, 2025.

This Booking.com deal was found by Cheapflights users on 3/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/218:07 pmSAN - ORF
2 stops10h 33mSpirit Airlines
Fri 3/2810:45 amORF - SAN
2 stops23h 56mSpirit Airlines
Deal found 3/1$319
This Mytrip deal was found by Cheapflights users on 3/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1712:48 pmSAN - ORF
Nonstop5h 22mMultiple Airlines
Sun 5/259:24 amORF - SAN
2 stops25h 04mMultiple Airlines
Deal found 3/1$326
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2812:48 pmSAN - ORF
Nonstop5h 22mBreeze Airways
Wed 6/49:22 amORF - SAN
Nonstop5h 41mBreeze Airways
Deal found 3/2$333
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/111:35 amSAN - ORF
1 stop7h 51mDelta
Tue 4/84:03 pmORF - SAN
1 stop10h 44mDelta
Deal found 3/3$339
This Southwest deal was found by Cheapflights users on 3/3. 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 4/16:30 amSAN - ORF
1 stop7h 40mSouthwest
Tue 4/82:25 pmORF - SAN
2 stops10h 40mSouthwest
Deal found 3/3$344
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 4/1210:45 pmSAN - ORF
1 stop8h 27mAmerican Airlines
Sun 4/206:23 amORF - SAN
1 stop8h 25mAmerican Airlines
Deal found 3/3$348
This United Airlines deal was found by Cheapflights users on 3/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1711:10 amSAN - ORF
1 stop9h 26mUnited Airlines
Sun 5/256:00 amORF - SAN
2 stops9h 46mUnited Airlines
Deal found 3/1$362
This Alaska Airlines deal was found by Cheapflights users on 3/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/87:00 amSAN - ORF
2 stops11h 58mAlaska Airlines
Sun 3/93:16 pmORF - SAN
2 stops11h 43mAlaska Airlines
Deal found 3/2$899

Find flights from San Diego to Chesapeake within your budget

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 March 3, 2025.

Fly from

San Diego

Fly to

Chesapeake

Route

Depart

Return

Price

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 3/21

8:07 pm-9:40 am

2 stops10h 33m

Norfolk

Fri 3/28

10:45 am-7:41 am

2 stops23h 56m

$319

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 5/17

12:48 pm-9:10 pm

Nonstop5h 22m

Norfolk

Sun 5/25

9:24 am-7:28 am

2 stops25h 04m

$326

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 5/28

12:48 pm-9:10 pm

Nonstop5h 22m

Norfolk

Wed 6/4

9:22 am-12:03 pm

Nonstop5h 41m

$333

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Tue 4/1

11:35 am-10:26 pm

1 stop7h 51m

Norfolk

Tue 4/8

4:03 pm-11:47 pm

1 stop10h 44m

$339

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Tue 4/1

6:30 am-5:10 pm

1 stop7h 40m

Norfolk

Tue 4/8

2:25 pm-10:05 pm

2 stops10h 40m

$344

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 4/12

10:45 pm-10:12 am

1 stop8h 27m

Norfolk

Sun 4/20

6:23 am-11:48 am

1 stop8h 25m

$348

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 5/17

11:10 am-11:36 pm

1 stop9h 26m

Norfolk

Sun 5/25

6:00 am-12:46 pm

2 stops9h 46m

$362

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 3/8

7:00 am-9:58 pm

2 stops11h 58m

Norfolk

Sun 3/9

3:16 pm-11:59 pm

2 stops11h 43m

$899

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 3/26

8:07 pm-11:47 am

2 stops12h 40m

$125

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 3/20

10:17 pm-11:54 am

1 stop10h 37m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 14 results
1
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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.

Travel insights for flights from San Diego to Chesapeake

Get recent, data-driven insights about flights from San Diego to Chesapeake including ideal travel times, pricing trends, and more.

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 February 28, 2025.

Booking 82 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, January is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $281). Flying from San Diego to Chesapeake in June is currently the most expensive (average of $372). 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.

What is the cheapest time of day to fly from SAN to C6E?

Find hourly flight availability from San Diego to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Diego to Chesapeake as you normally would.

What is the cheapest day to fly from San Diego to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from San Diego to Chesapeake. Price data was last updated on March 2, 2025.

Travelers seeking maximum savings on their San Diego to Chesapeake flight should consider departing on Saturday afternoons when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 March 3, 2025.
Get a feel of what it's like to fly with Southwest, Breeze Airways and Delta from San Diego to Chesapeake by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,333 reviews
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Breeze Airways
8.1
Very good
152 reviews
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,068 reviews
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

United Airlines
7.4
Good
8,679 reviews
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $125. 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, January is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $281). Flying from San Diego to Chesapeake in June is currently the most expensive (average of $372). 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.

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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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$145Average$282FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$147Average$291FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$213Average$487FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$465FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$285Average$530FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$356Average$476FlexibilityNo cancel feeOn-time63%
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