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Chesapeake

$98+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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Cheap 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 February 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 3/26:00 am
SAT
-
ORF
1 stop29h 05m
Multiple Airlines
Thu 3/57:13 pm
ORF
-
SAT
1 stop29h 46m
Multiple Airlines
Deal found 2/16$203
This Priceline deal was found by Cheapflights users on 2/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1710:22 am
SAT
-
ORF
1 stop8h 24m
Spirit Airlines
Tue 3/246:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/16$207
This Priceline deal was found by Cheapflights users on 2/13. 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.
Sat 3/2110:22 am
SAT
-
ORF
1 stop8h 24m
Spirit Airlines
Wed 3/256:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/13$209
This Mytrip deal was found by Cheapflights users on 2/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:26 am
SAT
-
ORF
1 stop7h 00m
Spirit Airlines
Mon 3/168:41 pm
ORF
-
SAT
1 stop13h 46m
Spirit Airlines
Deal found 2/16$214
This CheapOair deal was found by Cheapflights users on 2/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
SAT
-
ORF
1 stop15h 58m
Spirit Airlines
Wed 5/276:05 am
ORF
-
SAT
1 stop17h 13m
Spirit Airlines
Deal found 2/13$216
This Priceline deal was found by Cheapflights users on 2/13. 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.
Thu 3/191:22 pm
SAT
-
ORF
1 stop7h 25m
Spirit Airlines
Tue 3/246:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/13$221
This Mytrip deal was found by Cheapflights users on 2/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:26 am
SAT
-
ORF
1 stop7h 00m
Spirit Airlines
Tue 3/107:31 pm
ORF
-
SAT
1 stop14h 59m
Spirit Airlines
Deal found 2/13$232
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Wed 3/1110:26 am
SAT
-
ORF
2 stops22h 49m
Multiple Airlines
Mon 3/168:41 pm
ORF
-
SAT
1 stop13h 46m
Multiple Airlines
Deal found 2/15$235
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Thu 3/2610:22 am
SAT
-
ORF
2 stops23h 16m
Multiple Airlines
Wed 4/18:41 pm
ORF
-
SAT
1 stop13h 46m
Multiple Airlines
Deal found 2/15$236
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
SAT
-
ORF
1 stop29h 05m
Multiple Airlines
Fri 3/66:45 am
ORF
-
SAT
1 stop7h 53m
Multiple Airlines
Deal found 2/14$237
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/221:22 pm
SAT
-
ORF
1 stop24h 09m
Multiple Airlines
Wed 3/256:45 am
ORF
-
SAT
1 stop6h 42m
Multiple Airlines
Deal found 2/13$242

Find 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 February 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Kiwi.com)

One-way from

$98
(Priceline)

Popular in

January

Cheapest in

August

Average price

$398
Provider with most accurate pricing for San Antonio-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Antonio-Norfolk flights.
Search Deals
From San Antonio to Chesapeake
Search Deals
One-way flight from San Antonio to Chesapeake
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($136 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 16, 2026.
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

Wed 3/11

10:26 am-6:26 pm

1 stop7h 00m

Norfolk

Mon 3/16

8:41 pm-9:27 am

1 stop13h 46m

$216

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Wed 3/11

10:26 am-10:15 am

2 stops22h 49m

Norfolk

Mon 3/16

8:41 pm-9:27 am

1 stop13h 46m

$235

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Sun 3/22

1:22 pm-11:38 am

2 stops21h 16m

Norfolk

Wed 3/25

6:45 am-12:27 pm

1 stop6h 42m

$260

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Sat 3/21

10:22 am-7:46 pm

1 stop8h 24m

Norfolk

Wed 3/25

6:45 am-9:27 am

2 stops27h 42m

$266

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 3/20

1:22 pm-9:47 pm

1 stop7h 25m

Norfolk

Sun 3/29

6:45 am-12:27 pm

1 stop6h 42m

$273

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 3/3

10:26 am-6:26 pm

1 stop7h 00m

Norfolk

Tue 3/10

8:05 am-9:30 am

2 stops26h 25m

$273

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 3/17

10:22 am-9:47 pm

3 stops34h 25m

Norfolk

Wed 3/25

8:41 pm-9:27 am

1 stop13h 46m

$281

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 3/17

10:22 am-9:47 pm

3 stops34h 25m

Norfolk

Tue 3/24

6:45 am-12:27 pm

1 stop6h 42m

$281

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Wed 3/11

10:26 am-6:26 pm

1 stop7h 00m

Norfolk

Sun 3/15

9:30 pm-9:27 am

2 stops36h 57m

$285

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 3/13

2:40 pm-2:31 pm

1 stop22h 51m

Norfolk

Thu 3/19

8:41 pm-9:27 am

1 stop13h 46m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 23 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 February 13, 2026.

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, March is the cheapest month in which you can book a flight from San Antonio to Chesapeake (average of $115). Flying from San Antonio to Chesapeake in April is currently the most expensive (average of $288). 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 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 February 16, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and American 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
4,285 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,285 reviews
Southwest
8.0
Very good
4,285 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,206 reviews
Southwest
8.0
Very good
4,285 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,290 reviews
Southwest
8.0
Very good
4,285 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,456 reviews
Southwest
8.0
Very good
4,285 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 4 different airlines.

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

    For as low as $216, Spirit Airlines can have you in Chesapeake from San Antonio in 7h. Airlines will cover a distance of 1379 mi.

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

    $44 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $127 and $163, 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, March is the cheapest month in which you can book a flight from San Antonio to Chesapeake (average of $115). Flying from San Antonio to Chesapeake in April is currently the most expensive (average of $288). 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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Alternative routes for San Antonio to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from San Antonio to Chesapeake

Discover the top 4 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 February 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$280FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$238Average$456FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$259Average$469FlexibilityNo cancel feeOn-time71%
DeltaCheapest$298Average$452FlexibilityNo cancel feeOn-timeN/A

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