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Chesapeake

$129+ Cheap flights from San Antonio (SAT) 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from San Antonio to Chesapeake are usually found in August or February, booked 52 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

Cheap flight deals from San Antonio to Chesapeake

Keep the following information in mind while searching for San Antonio to Chesapeake flight deals. Data was last updated September 17, 2025.

Round-trip from

$217
(Priceline)

One-way from

$129
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$385
From San Antonio to Chesapeake
Search Deals
One-way flight from San Antonio to Chesapeake
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from San Antonio to Chesapeake

Cheapest flights from San Antonio to Chesapeake
Explore the most affordable flight options available from San Antonio to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Priceline deal was found by Cheapflights users on 9/14. 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.
Fri 11/144:16 pmSAT - ORF
1 stop6h 24mMultiple Airlines
Mon 11/1711:29 amORF - SAT
1 stop6h 11mMultiple Airlines
Deal found 9/14$217
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/22:54 pmSAT - ORF
1 stop24h 49mSpirit Airlines
Sun 10/55:38 pmORF - SAT
1 stop23h 12mSpirit Airlines
Deal found 9/16$237
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/22:54 pmSAT - ORF
2 stops19h 30mMultiple Airlines
Sun 10/55:38 pmORF - SAT
1 stop23h 12mMultiple Airlines
Deal found 9/16$268
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/37:17 pmSAT - ORF
1 stop26h 31mSpirit Airlines
Sun 10/55:38 pmORF - SAT
1 stop23h 12mSpirit Airlines
Deal found 9/16$279
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/215:00 amSAT - ORF
1 stop8h 54mAmerican Airlines
Sat 10/253:44 pmORF - SAT
1 stop7h 55mAmerican Airlines
Deal found 9/15$294
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/167:35 pmSAT - ORF
1 stop26h 11mSpirit Airlines
Mon 10/205:24 amORF - SAT
1 stop14h 06mSpirit Airlines
Deal found 9/16$295
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:45 amSAT - ORF
1 stop6h 40mAmerican Airlines
Tue 10/216:41 amORF - SAT
1 stop12h 04mAmerican Airlines
Deal found 9/16$300
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:00 amSAT - ORF
1 stop8h 54mAmerican Airlines
Sat 11/13:44 pmORF - SAT
1 stop7h 55mAmerican Airlines
Deal found 9/16$313
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/297:17 pmSAT - ORF
2 stops17h 10mMultiple Airlines
Thu 10/25:20 amORF - SAT
1 stop13h 52mMultiple Airlines
Deal found 9/15$321

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Antonio 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 September 17, 2025.
Use the filters below to find and compare flights from San Antonio to Chesapeake that are best for you.

Fly from

San Antonio

Fly to

Chesapeake

Route

Depart

Return

Price

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 10/21

5:00 am-2:54 pm

1 stop8h 54m

Norfolk

Sat 10/25

3:44 pm-10:39 pm

1 stop7h 55m

$294

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 10/3

7:17 pm-4:43 pm

2 stops20h 26m

Norfolk

Sun 10/5

5:38 pm-3:50 pm

1 stop23h 12m

$306

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 11/14

4:16 pm-10:03 pm

2 stops28h 47m

Norfolk

Mon 11/17

11:29 am-4:40 pm

1 stop6h 11m

$318

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Mon 9/29

7:17 pm-1:27 pm

2 stops17h 10m

Norfolk

Thu 10/2

5:20 am-6:12 pm

1 stop13h 52m

$321

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Wed 10/29

12:45 pm-9:05 pm

2 stops7h 20m

Norfolk

Sat 11/1

4:45 pm-9:00 pm

1 stop5h 15m

$335

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 10/21

2:20 pm-9:05 pm

1 stop5h 45m

Norfolk

Sat 10/25

8:35 am-4:45 pm

2 stops9h 10m

$335

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 10/31

6:00 am-2:54 pm

1 stop7h 54m

Norfolk

Mon 11/3

7:29 pm-12:28 am

1 stop5h 59m

$350

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Wed 10/15

6:05 am-1:25 pm

1 stop6h 20m

Norfolk

Sun 10/19

5:00 am-9:21 am

1 stop5h 21m

$372

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 11/14

6:00 am-11:40 pm

2 stops16h 40m

Norfolk

Mon 11/17

6:00 am-10:27 pm

2 stops17h 27m

$376

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 10/24

3:02 pm-10:58 pm

1 stop6h 56m

Norfolk

Sun 10/26

7:19 pm-8:21 am

1 stop14h 02m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 22 results
1
2
3

Best time to book a flight from San Antonio to Chesapeake

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

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

Use this chart to determine the optimal time to book a round-trip flight from San Antonio to Chesapeake. Price data was last updated on September 12, 2025.

The price you pay for your flight from San Antonio to Chesapeake may vary depending on when you book. For the best chance of a lower fare, look to book 52 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 San Antonio to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from San Antonio to Chesapeake (average of $281). Flying from San Antonio to Chesapeake in March is currently the most expensive (average of $351). 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 SAT to C6E?

Find hourly flight availability from San Antonio 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 September 17, 2025.

When flying from San Antonio to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from San Antonio to Chesapeake to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from San Antonio 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 Antonio to Chesapeake?

    If you book a flight to Chesapeake from San Antonio, you will be flying from San Antonio, which is the city’s only airport. San Antonio (SAT) is located 7.6 mi from the center of San Antonio. There are 0 flights from San Antonio to Chesapeake per day from 5 different airlines.

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

    For as low as $335, American Airlines can have you in Chesapeake from San Antonio in 7h 20m. Airlines will cover a distance of 1379 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $159 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $162 and $164, respectively.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from San Antonio to Chesapeake (average of $281). Flying from San Antonio to Chesapeake in March is currently the most expensive (average of $351). 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 5 airlines flying from San Antonio to Chesapeake

Discover the top 5 airlines that operate flights from San Antonio 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$134Average$315FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$238Average$473FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$253Average$436FlexibilityNo cancel feeOn-time71%
DeltaCheapest$298Average$432FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$316Average$526FlexibilityNo cancel feeOn-time69%

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