Chesapeake

$95+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Mar 31 — Apr 71
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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 March 1, 2026.

This Priceline deal was found by Cheapflights users on 2/26. 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 3/2410:22 am
SAT
-
ORF
1 stop8h 24m
Spirit Airlines
Wed 4/16:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/26$219
This CheapOair deal was found by Cheapflights users on 2/26. 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.
Tue 4/71:22 pm
SAT
-
ORF
1 stop7h 25m
Multiple Airlines
Thu 4/168:41 pm
ORF
-
SAT
1 stop13h 43m
Multiple Airlines
Deal found 2/26$220
This Priceline deal was found by Cheapflights users on 2/26. 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 3/2410:22 am
SAT
-
ORF
1 stop8h 24m
Spirit Airlines
Tue 4/76:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/26$221
This Priceline deal was found by Cheapflights users on 2/26. 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 3/231:22 pm
SAT
-
ORF
1 stop7h 25m
Spirit Airlines
Thu 3/266:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/26$223
This CheapOair deal was found by Cheapflights users on 2/26. 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.
Thu 3/1910:22 am
SAT
-
ORF
1 stop8h 24m
Spirit Airlines
Thu 3/266:45 am
ORF
-
SAT
1 stop6h 42m
Spirit Airlines
Deal found 2/26$231
This Kiwi.com deal was found by Cheapflights users on 2/27. 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.
Sat 4/186:30 pm
SAT
-
ORF
1 stop18h 50m
Multiple Airlines
Mon 4/2711:27 am
ORF
-
SAT
2 stops53h 26m
Multiple Airlines
Deal found 2/27$237
This Mytrip deal was found by Cheapflights users on 2/26. 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 3/2410:22 am
SAT
-
ORF
1 stop8h 24m
Spirit Airlines
Mon 4/68:41 pm
ORF
-
SAT
1 stop13h 46m
Spirit Airlines
Deal found 2/26$238
This Expedia deal was found by Cheapflights users on 2/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:22 pm
SAT
-
ORF
1 stop7h 25m
Multiple Airlines
Mon 4/611:33 am
ORF
-
SAT
1 stop6h 32m
Multiple Airlines
Deal found 2/26$242
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Tue 3/242:13 pm
SAT
-
ORF
1 stop24h 38m
Multiple Airlines
Mon 4/611:33 am
ORF
-
SAT
2 stops37h 46m
Multiple Airlines
Deal found 2/26$244
This CheapOair deal was found by Cheapflights users on 2/25. 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.
Thu 4/166:00 am
SAT
-
ORF
1 stop15h 58m
Spirit Airlines
Sun 4/198:27 pm
ORF
-
SAT
1 stop13h 44m
Spirit Airlines
Deal found 2/25$252
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 5/73:14 pm
SAT
-
ORF
2 stops18h 10m
Multiple Airlines
Sun 5/108:27 pm
ORF
-
SAT
1 stop13h 44m
Multiple Airlines
Deal found 2/25$254

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 March 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Priceline)

One-way from

$95
(Priceline)

Popular in

January

Cheapest in

August

Average price

$395
Provider with most accurate pricing for San Antonio-Norfolk flight deals.
Provider most trusted by Cheapflights users for San Antonio-Norfolk flights.
From San Antonio to Chesapeake
One-way flight from San Antonio to Chesapeake
Highest demand for flights based on searches. 25% potential increase in price ($150 potential increase over avg. RT price).
Cheapest flight prices on average. 9% potential price decrease ($41 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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 March 1, 2026.
Use the filters below to find and compare flights from San Antonio to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 8/21

5:45 am-10:54 am

1 stop28h 09m

Norfolk

Sun 8/23

6:00 am-10:06 pm

1 stop17h 06m

$354

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 4/7

12:45 pm-9:10 pm

2 stops7h 25m

Norfolk

Wed 4/15

8:40 am-3:10 pm

2 stops7h 30m

$377

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Thu 4/16

2:02 pm-9:08 pm

1 stop6h 06m

Norfolk

Mon 4/20

5:05 pm-10:58 pm

1 stop6h 53m

$385

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Sat 6/13

4:00 pm-11:33 pm

1 stop6h 33m

Norfolk

Tue 6/23

5:30 am-9:48 am

1 stop5h 18m

$427

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Thu 6/18

4:18 pm-10:30 pm

1 stop5h 12m

Norfolk

Tue 6/23

5:50 am-12:30 pm

1 stop7h 40m

$427

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 8/21

5:30 am-12:49 pm

1 stop6h 19m

Norfolk

Sun 8/23

7:00 am-1:07 pm

1 stop7h 07m

$427

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 6/26

5:18 pm-12:41 am

1 stop6h 23m

Norfolk

Tue 6/30

11:30 am-7:50 pm

2 stops9h 20m

$432

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 4/7

5:30 am-2:20 pm

2 stops7h 50m

Norfolk

Thu 4/16

10:27 am-5:43 pm

2 stops8h 16m

$433

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Mon 4/20

2:02 pm-9:08 pm

1 stop6h 06m

Norfolk

Fri 4/24

6:00 am-12:24 pm

1 stop7h 24m

$450

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Mon 6/29

3:40 pm-11:35 pm

2 stops6h 55m

Norfolk

Fri 7/10

3:30 pm-10:50 pm

2 stops8h 20m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 24 resultsSorted by cheapest first
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 27, 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 $116). 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 March 1, 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.

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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 $385, Spirit Airlines can have you in Chesapeake from San Antonio in 6h 06m. 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?

    $48 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 $116). 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.

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 March 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$193Average$322FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$238Average$449FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$259Average$473FlexibilityNo cancel feeOn-time71%
DeltaCheapest$298Average$452FlexibilityNo cancel feeOn-timeN/A

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