$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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Sep 13 — Sep 201
Round-trip
1 adult, Economy
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Find cheap flights from San Antonio to Chesapeake with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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One-way
Cheapest flights from San Antonio to ChesapeakeExplore 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 14, 2026.
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 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/1410:05 am -
2 stops25h 24m
Tue 9/227:43 pm -
1 stop14h 24m
Deal found 8/11![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/1110:05 am -
1 stop7h 43m
Sun 9/131:18 pm -
2 stops31h 07m
Deal found 8/12![Frontier logo]()
$281
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:46 pm -
1 stop7h 50m
Sat 11/148:40 am -
1 stop7h 58m
Deal found 8/13![Delta logo]()
$293
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 9/108:55 am -
1 stop6h 36m
Thu 9/175:30 am -
1 stop6h 06m
Deal found 8/12![American Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 8/10. 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.
Tue 10/207:20 am -
2 stops7h 50m
Tue 10/274:45 pm -
1 stop5h 25m
Deal found 8/10![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/112:05 pm -
2 stops6h 35m
Mon 9/146:45 pm -
1 stop5h 35m
Deal found 8/12![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 9/35:20 am -
1 stop6h 25m
Thu 9/106:00 am -
1 stop5h 39m
Deal found 8/11![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop8h 17m
Sat 11/143:47 pm -
2 stops8h 09m
Deal found 8/13![American Airlines logo]()
$312
Best flights from San Antonio to ChesapeakeDiscover carefully curated flight deals from San Antonio to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2026.
Discover carefully curated flight deals from San Antonio to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2026.
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:46 pm -
1 stop7h 50m
Sat 11/148:40 am -
1 stop7h 58m
Deal found 8/13![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:35 am -
1 stop7h 41m
Wed 9/305:01 pm -
1 stop6h 49m
Deal found 8/13![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/1412:20 pm -
2 stops8h 20m
Tue 9/223:20 pm -
2 stops8h 50m
Deal found 8/11![Southwest logo]()
$395
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 9/35:20 am -
1 stop6h 25m
Thu 9/106:00 am -
1 stop5h 39m
Deal found 8/11![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 12/236:45 am -
1 stop6h 18m
Tue 12/297:40 pm -
1 stop5h 48m
Deal found 8/12![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 9/31:00 pm -
2 stops7h 40m
Thu 9/101:05 pm -
2 stops9h 35m
Deal found 8/11![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:50 am -
2 stops9h 00m
Wed 9/28:50 am -
2 stops7h 50m
Deal found 8/13![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 8/9. 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.
Fri 9/111:20 pm -
1 stop8h 21m
Mon 9/147:19 pm -
1 stop5h 49m
Deal found 8/9![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 8/11. 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.
Mon 11/301:46 pm -
1 stop5h 36m
Fri 12/43:00 pm -
1 stop7h 58m
Deal found 8/11![Delta logo]()
$416
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:20 am -
1 stop5h 19m
Wed 9/21:51 pm -
1 stop8h 13m
Deal found 8/13![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 8/10. 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.
Sun 10/115:15 am -
1 stop5h 30m
Sun 10/256:00 am -
1 stop5h 40m
Deal found 8/10![Delta logo]()
$457
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated August 14, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated August 14, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 9/35:20 am -
1 stop6h 25m
Thu 9/106:00 am -
1 stop5h 39m
Deal found 8/11![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Thu 9/37:00 am -
1 stop7h 08m
Thu 9/103:45 pm -
2 stops7h 14m
Deal found 8/11![American Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/810:24 pm -
2 stops37h 05m
Tue 9/157:43 pm -
1 stop14h 24m
Deal found 8/9![Frontier logo]()
$315
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 9/108:55 am -
1 stop6h 36m
Thu 9/175:30 am -
1 stop6h 06m
Deal found 8/12![American Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/1110:05 am -
1 stop7h 43m
Sun 9/131:18 pm -
2 stops31h 07m
Deal found 8/12![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/112:55 pm -
1 stop5h 45m
Mon 9/146:45 pm -
1 stop5h 35m
Deal found 8/12![Southwest logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/1410:05 am -
2 stops25h 24m
Tue 9/227:43 pm -
1 stop14h 24m
Deal found 8/11![Frontier logo]()
$277
One-way flights from San Antonio to ChesapeakeSearch for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
This Expedia deal was found by Cheapflights users on 8/12. 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 9/2510:05 am -
1 stop7h 43m
Deal found 8/12![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/319:51 am -
1 stop29h 20m
Deal found 8/10![Frontier logo]()
$143
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Sat 10/106:00 pm -
1 stop4h 57m
Deal found 8/12![American Airlines logo]()
$147
This Southwest deal was found by Cheapflights users on 8/9. 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 10/217:20 am -
2 stops7h 50m
Deal found 8/9![Southwest logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 8/295:38 pm -
3 stops17h 47m
Deal found 8/9![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 9/249:25 am -
2 stops53h 25m
Deal found 8/13![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 8/3111:30 am -
3 stops27h 41m
Deal found 8/9![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 11/157:56 pm -
2 stops39h 06m
Deal found 8/11![Frontier logo]()
$179
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 August 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (Kiwi.com) |
One-way from | $129 (Expedia) |
Popular in | January |
Cheapest in | February |
Average price | $402 |
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 14, 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
Cheapest round-trip
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 11/12
1:46 pm-10:36 pm
1 stop7h 50m
Norfolk
Sat 11/14
8:40 am-3:38 pm
1 stop7h 58m
$293
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 9/3
5:20 am-12:45 pm
1 stop6h 25m
Norfolk
Thu 9/10
6:00 am-10:39 am
1 stop5h 39m
$305
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 12/23
6:45 am-2:03 pm
1 stop6h 18m
Norfolk
Tue 12/29
7:40 pm-12:28 am
1 stop5h 48m
$375
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Sat 9/26
6:35 am-3:16 pm
1 stop7h 41m
Norfolk
Wed 9/30
5:01 pm-10:50 pm
1 stop6h 49m
$383
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Mon 9/14
12:20 pm-9:40 pm
2 stops8h 20m
Norfolk
Tue 9/22
3:20 pm-11:10 pm
2 stops8h 50m
$395
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Fri 9/11
1:20 pm-10:41 pm
1 stop8h 21m
Norfolk
Mon 9/14
7:19 pm-12:08 am
1 stop5h 49m
$406
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Mon 11/30
1:46 pm-8:22 pm
1 stop5h 36m
Norfolk
Fri 12/4
3:00 pm-9:58 pm
1 stop7h 58m
$416
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 9/3
1:00 pm-9:40 pm
2 stops7h 40m
Norfolk
Thu 9/10
1:05 pm-9:40 pm
2 stops9h 35m
$432
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 8/26
5:20 am-11:39 am
1 stop5h 19m
Norfolk
Wed 9/2
1:51 pm-9:04 pm
1 stop8h 13m
$436
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 8/26
10:50 am-8:50 pm
2 stops9h 00m
Norfolk
Wed 9/2
8:50 am-3:40 pm
2 stops7h 50m
$446
Showing 1-10 of 21 resultsSorted by cheapest first
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.
SAT-ORF
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
SAT-C6E
SAT-ORF
How much does it cost to fly round-trip from San Antonio to Chesapeake?
Airfare is below average for this route at the moment.
San Antonio to Chesapeake flights typically cost between $386 and $541 in September.The cheapest round-trip price found within the last 5 days was $277 on Frontier (Sep 14-Sep 22).
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 14, 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
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
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Complete your trip
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Find flights from San Antonio to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Antonio and Chesapeake flights
Browse other San Antonio and Chesapeake flight options. Last updated on August 14, 2026.
Other flights from San Antonio
Browse through other flights departing from San Antonio. Flights are based on user searches made on Cheapflights and were last updated on August 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San Antonio to Chesapeake flights
Consider these flights traveling from San Antonio to Chesapeake.
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 August 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$288 | Average$464 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$298 | Average$491 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$365 | Average$471 | FlexibilityNo cancel fee | On-time63% |