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Chesapeake

$84+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$214
(FlightHub)

One-way from

$84
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$346
From San Antonio to Chesapeake
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One-way flight from San Antonio to Chesapeake
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Highest demand for flights based on searches. 11% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 20, 2025.

This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:19 pmSAT - ORF
1 stop26h 27mMultiple Airlines
Mon 11/311:42 amORF - SAT
1 stop5h 58mMultiple Airlines
Deal found 8/18$214
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:33 amSAT - ORF
1 stop22h 51mMultiple Airlines
Mon 10/65:24 amORF - SAT
1 stop13h 49mMultiple Airlines
Deal found 8/18$222
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:45 pmSAT - ORF
1 stop26h 58mSpirit Airlines
Sun 10/55:38 pmORF - SAT
1 stop23h 17mSpirit Airlines
Deal found 8/18$243
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/175:45 pmSAT - ORF
1 stop17h 42mMultiple Airlines
Sun 10/195:38 pmORF - SAT
1 stop25h 37mMultiple Airlines
Deal found 8/19$255
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/1912:45 pmSAT - ORF
1 stop26h 58mSpirit Airlines
Mon 9/225:20 amORF - SAT
1 stop13h 52mSpirit Airlines
Deal found 8/19$257
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:19 pmSAT - ORF
1 stop26h 27mSpirit Airlines
Sun 10/195:38 pmORF - SAT
1 stop23h 17mSpirit Airlines
Deal found 8/18$259
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/165:00 amSAT - ORF
1 stop8h 52mAmerican Airlines
Tue 9/236:34 amORF - SAT
1 stop12h 13mAmerican Airlines
Deal found 8/19$283
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/1712:44 pmSAT - ORF
1 stop8h 52mAmerican Airlines
Wed 9/2411:14 amORF - SAT
1 stop5h 35mAmerican Airlines
Deal found 8/19$290
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/35:40 pmSAT - ORF
2 stops22h 03mMultiple Airlines
Sun 10/55:24 amORF - SAT
1 stop13h 49mMultiple Airlines
Deal found 8/18$293

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 August 20, 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

Fri 10/31

7:19 pm-10:46 pm

1 stop26h 27m

Norfolk

Mon 11/3

11:42 am-4:40 pm

1 stop5h 58m

$214

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Thu 10/2

11:33 am-11:24 am

1 stop22h 51m

Norfolk

Mon 10/6

5:24 am-6:13 pm

1 stop13h 49m

$222

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 10/3

12:45 pm-4:43 pm

1 stop26h 58m

Norfolk

Sun 10/5

5:38 pm-3:55 pm

1 stop23h 17m

$243

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 10/17

5:45 pm-12:27 pm

1 stop17h 42m

Norfolk

Sun 10/19

5:38 pm-6:15 pm

1 stop25h 37m

$255

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 9/19

12:45 pm-4:43 pm

1 stop26h 58m

Norfolk

Mon 9/22

5:20 am-6:12 pm

1 stop13h 52m

$257

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Thu 10/16

7:19 pm-10:46 pm

1 stop26h 27m

Norfolk

Sun 10/19

5:38 pm-3:55 pm

1 stop23h 17m

$259

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 9/19

12:45 pm-4:43 pm

1 stop26h 58m

Norfolk

Sun 9/21

5:20 am-6:12 pm

1 stop13h 52m

$259

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 9/16

5:00 am-2:52 pm

1 stop8h 52m

Norfolk

Tue 9/23

6:34 am-5:47 pm

1 stop12h 13m

$283

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Thu 9/25

11:33 am-11:24 am

1 stop22h 51m

$84

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Sat 10/25

5:32 pm-11:44 am

2 stops17h 12m

$121

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 20 results
1
2

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 August 8, 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 August 20, 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 August 20, 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
4,246 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,039 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 $243, Spirit Airlines can have you in Chesapeake from San Antonio in 26h 58m. Airlines will cover a distance of 1379 mi.

  • 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$134Average$295FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$238Average$469FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$253Average$432FlexibilityNo cancel feeOn-time71%
DeltaCheapest$298Average$428FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$324Average$526FlexibilityNo cancel feeOn-time69%

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