Chesapeake

$150+ 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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Jul 19 — Jul 261
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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 June 19, 2026.

This CheapOair deal was found by Cheapflights users on 6/17. 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.
Fri 7/179:51 am
SAT
-
ORF
1 stop9h 48m
Frontier
Fri 7/249:34 pm
ORF
-
SAT
1 stop19h 07m
Frontier
Deal found 6/17$298
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:51 am
SAT
-
ORF
1 stop10h 10m
Frontier
Sun 8/239:56 pm
ORF
-
SAT
1 stop12h 00m
Frontier
Deal found 6/17$308
This Expedia deal was found by Cheapflights users on 6/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:51 am
SAT
-
ORF
1 stop9h 48m
Frontier
Sun 7/199:34 pm
ORF
-
SAT
1 stop12h 22m
Frontier
Deal found 6/14$310
This Frontier deal was found by Cheapflights users on 6/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:51 am
SAT
-
ORF
1 stop10h 10m
Frontier
Thu 8/279:56 pm
ORF
-
SAT
1 stop12h 00m
Frontier
Deal found 6/15$324
This Expedia deal was found by Cheapflights users on 6/17. 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.
Fri 7/249:51 am
SAT
-
ORF
1 stop9h 48m
Frontier
Sun 7/269:34 pm
ORF
-
SAT
1 stop12h 22m
Frontier
Deal found 6/17$338
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:37 pm
SAT
-
ORF
1 stop9h 41m
Delta
Tue 7/146:05 am
ORF
-
SAT
1 stop5h 29m
Delta
Deal found 6/14$347
This Orbitz deal was found by Cheapflights users on 6/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:51 am
SAT
-
ORF
1 stop9h 48m
Frontier
Thu 7/169:34 pm
ORF
-
SAT
1 stop12h 22m
Frontier
Deal found 6/17$348
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 8/266:00 am
SAT
-
ORF
2 stops7h 02m
American Airlines
Wed 9/24:00 pm
ORF
-
SAT
1 stop6h 15m
American Airlines
Deal found 6/15$352
This Booking.com deal was found by Cheapflights users on 6/17. 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.
Sat 7/114:26 pm
SAT
-
ORF
1 stop27h 13m
Frontier
Thu 7/169:34 pm
ORF
-
SAT
1 stop12h 22m
Frontier
Deal found 6/17$356
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:40 am
SAT
-
ORF
2 stops9h 40m
Southwest
Wed 9/28:50 am
ORF
-
SAT
2 stops7h 50m
Southwest
Deal found 6/15$357
This Frontier deal was found by Cheapflights users on 6/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:51 am
SAT
-
ORF
1 stop9h 48m
Frontier
Sun 7/199:34 pm
ORF
-
SAT
1 stop12h 22m
Frontier
Deal found 6/14$359

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 June 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$298
(CheapOair)

One-way from

$150
(Priceline)

Popular in

January

Cheapest in

September

Average price

$449
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. 23% potential increase in price ($135 potential increase over avg. RT price).
Cheapest flight prices on average. 11% potential price decrease ($46 potential savings vs. average RT price).
Average for round-trip flights in June 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 June 19, 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

Cheapest round-trip

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Thu 8/6

5:45 pm-1:03 am

1 stop6h 18m

Norfolk

Sun 8/9

6:00 am-10:34 am

1 stop5h 34m

$411

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 9/11

12:20 pm-9:55 pm

2 stops8h 35m

Norfolk

Mon 9/14

6:25 am-12:00 pm

1 stop6h 35m

$416

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Tue 9/1

1:00 pm-9:41 pm

1 stop7h 41m

Norfolk

Wed 9/2

6:00 am-11:52 am

1 stop6h 52m

$437
Quickest round-trip

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 7/17

5:15 am-12:03 pm

1 stop5h 48m

Norfolk

Fri 7/17

7:59 pm-12:20 am

1 stop5h 21m

$447

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Sat 7/25

5:50 am-3:15 pm

2 stops8h 25m

Norfolk

Sat 7/25

4:50 pm-10:10 pm

1 stop6h 20m

$452

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 7/17

3:20 pm-11:40 pm

2 stops7h 20m

Norfolk

Mon 7/20

4:30 pm-10:55 pm

2 stops7h 25m

$487

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 8/21

12:55 pm-9:41 pm

1 stop7h 46m

Norfolk

Thu 8/27

6:15 am-3:43 pm

2 stops10h 28m

$506

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Mon 8/3

1:35 pm-11:44 pm

2 stops9h 09m

Norfolk

Sat 8/8

10:40 am-10:57 pm

2 stops13h 17m

$616

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Sun 7/5

5:20 am-12:50 pm

2 stops6h 30m

Norfolk

Mon 7/6

6:00 am-1:25 pm

2 stops8h 25m

$626

San AntonioNorfolk

SAT - ORF

SATORF

San Antonio

Fri 7/3

3:45 pm-11:35 pm

2 stops6h 50m

Norfolk

Sun 7/5

6:15 pm-1:15 am

1 stop8h 00m

$671

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 17 resultsSorted by cheapest first
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 much does it cost to fly round-trip from San Antonio to Chesapeake?

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 June 19, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andAmerican 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.

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Comfort

8.0

Overall

7.9

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 3 different airlines.

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

    For as low as $411, Delta can have you in Chesapeake from San Antonio in 6h 18m. 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?

    $127 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, 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.

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 3 airlines flying from San Antonio to Chesapeake

Discover the top 3 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 June 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$472FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$471FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$469FlexibilityNo cancel feeOn-timeN/A

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