$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
1 adult, Economy
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Find cheap flights from San Antonio to Chesapeake with Cheapflights
1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Antonio to Chesapeake
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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 March 1, 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 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![Spirit Airlines logo]()
$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![Multiple Airlines logo]()
$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![Spirit Airlines logo]()
$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![Spirit Airlines logo]()
$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![Spirit Airlines logo]()
$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![Multiple Airlines logo]()
$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![Spirit Airlines logo]()
$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![Multiple Airlines logo]()
$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![Multiple Airlines logo]()
$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![Spirit Airlines logo]()
$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![Multiple Airlines logo]()
$254
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 March 1, 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 March 1, 2026.
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.
Fri 8/215:45 am
SAT
- ORF
1 stop28h 09m
Spirit Airlines
Sun 8/236:00 am
ORF
- SAT
1 stop17h 06m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$354
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:45 pm
SAT
- ORF
2 stops7h 25m
Southwest
Wed 4/158:40 am
ORF
- SAT
2 stops7h 30m
Southwest
Deal found 2/26![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 2/28. 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.
Thu 4/162:02 pm
SAT
- ORF
1 stop6h 06m
United Airlines
Mon 4/205:05 pm
ORF
- SAT
1 stop6h 53m
United Airlines
Deal found 2/28![United Airlines logo]()
$385
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/134:00 pm
SAT
- ORF
1 stop6h 33m
Delta
Tue 6/235:30 am
ORF
- SAT
1 stop5h 18m
Delta
Deal found 2/27![Delta logo]()
$427
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/184:18 pm
SAT
- ORF
1 stop5h 12m
United Airlines
Tue 6/235:50 am
ORF
- SAT
1 stop7h 40m
United Airlines
Deal found 2/25![United Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 2/28. 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 8/215:30 am
SAT
- ORF
1 stop6h 19m
Delta
Sun 8/237:00 am
ORF
- SAT
1 stop7h 07m
Delta
Deal found 2/28![Delta logo]()
$427
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/293:40 pm
SAT
- ORF
2 stops6h 55m
Southwest
Fri 7/103:30 pm
ORF
- SAT
2 stops8h 20m
Southwest
Deal found 2/26![Southwest logo]()
$467
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:18 pm
SAT
- ORF
1 stop6h 23m
United Airlines
Tue 6/3011:30 am
ORF
- SAT
2 stops9h 20m
United Airlines
Deal found 2/27![United Airlines logo]()
$432
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:30 am
SAT
- ORF
2 stops7h 50m
United Airlines
Thu 4/1610:27 am
ORF
- SAT
2 stops8h 16m
United Airlines
Deal found 2/26![United Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 2/28. 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 5/291:25 pm
SAT
- ORF
2 stops8h 30m
Southwest
Sun 5/3110:00 am
ORF
- SAT
2 stops8h 40m
Southwest
Deal found 2/28![Southwest logo]()
$497
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:02 pm
SAT
- ORF
1 stop6h 06m
United Airlines
Fri 4/246:00 am
ORF
- SAT
1 stop7h 24m
United Airlines
Deal found 2/25![United Airlines logo]()
$450
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:15 pm
SAT
- ORF
2 stops8h 21m
United Airlines
Sun 8/236:00 am
ORF
- SAT
1 stop7h 31m
United Airlines
Deal found 2/25![United Airlines logo]()
$512
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated March 1, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated March 1, 2026 and is based on user searches.
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.
Mon 3/161:22 pm
SAT
- ORF
1 stop7h 25m
Spirit Airlines
Mon 3/238:41 pm
ORF
- SAT
1 stop13h 46m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$272
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![Spirit Airlines logo]()
$231
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![Spirit Airlines logo]()
$223
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![Multiple Airlines logo]()
$242
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![Spirit Airlines logo]()
$219
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![Spirit Airlines logo]()
$221
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![Spirit Airlines logo]()
$238
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![Multiple Airlines logo]()
$244
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 March 1, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated 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.
Fri 4/1710:23 am
SAT
- ORF
1 stop6h 04m
Frontier
Deal found 2/26![Frontier logo]()
$95
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.
Thu 3/2610:22 am
SAT
- ORF
1 stop8h 24m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$105
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
SAT
- ORF
1 stop9h 51m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$112
This CheapOair deal was found by Cheapflights users on 2/28. 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 4/21:22 pm
SAT
- ORF
1 stop7h 25m
Spirit Airlines
Deal found 2/28![Spirit Airlines logo]()
$117
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 5/143:14 pm
SAT
- ORF
2 stops18h 10m
Frontier
Deal found 2/25![Frontier logo]()
$128
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.
Thu 5/73:14 pm
SAT
- ORF
2 stops18h 10m
Frontier
Deal found 2/26![Frontier logo]()
$130
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:12 pm
SAT
- ORF
1 stop25h 52m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$133
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.
Sun 4/192:12 pm
SAT
- ORF
1 stop25h 55m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$134
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.
Thu 3/2610:22 am
SAT
- ORF
2 stops23h 16m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$142
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.
Sun 4/192:59 pm
SAT
- ORF
2 stops18h 33m
Frontier
Deal found 2/27![Frontier logo]()
$148
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 |
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
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
Showing 1-10 of 24 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 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
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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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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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$193 | Average$322 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$238 | Average$449 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$259 | Average$473 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$298 | Average$452 | FlexibilityNo cancel fee | On-timeN/A |