$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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Aug 2 — Aug 91
Round-trip
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 July 3, 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 July 3, 2026.
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 8/169:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/28![Frontier logo]()
$288
This Travelocity deal was found by Cheapflights users on 7/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/279:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 7/309:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 7/2![Frontier logo]()
$318
This Frontier deal was found by Cheapflights users on 6/29. 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 7/249:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 7/269:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/29![Frontier logo]()
$319
This Booking.com deal was found by Cheapflights users on 7/2. 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.
Fri 10/29:57 am
SAT
- ORF
1 stop6h 18m
Frontier
Sun 10/116:25 pm
ORF
- SAT
1 stop16h 14m
Frontier
Deal found 7/2![Frontier logo]()
$321
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 8/139:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/28![Frontier logo]()
$338
This Delta deal was found by Cheapflights users on 6/28. 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.
Tue 8/46:25 am
SAT
- ORF
1 stop5h 20m
Delta
Sat 8/155:00 pm
ORF
- SAT
1 stop5h 04m
Delta
Deal found 6/28![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 6/28. 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.
Wed 7/295:20 am
SAT
- ORF
1 stop6h 25m
Delta
Tue 8/186:23 am
ORF
- SAT
1 stop5h 47m
Delta
Deal found 6/28![Delta logo]()
$344
This American Airlines deal was found by Cheapflights users on 6/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
SAT
- ORF
2 stops7h 02m
American Airlines
Mon 8/106:17 pm
ORF
- SAT
1 stop7h 31m
American Airlines
Deal found 6/27![American Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 7/1. 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 8/2910:53 am
SAT
- ORF
1 stop5h 15m
Delta
Tue 9/17:50 am
ORF
- SAT
1 stop6h 48m
Delta
Deal found 7/1![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 6/29. 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 7/2811:25 am
SAT
- ORF
2 stops9h 30m
Southwest
Tue 8/46:15 am
ORF
- SAT
1 stop5h 45m
Southwest
Deal found 6/29![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 7/1. 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.
Sat 8/295:40 am
SAT
- ORF
2 stops7h 30m
Southwest
Tue 9/16:15 pm
ORF
- SAT
1 stop5h 55m
Southwest
Deal found 7/1![Southwest logo]()
$352
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 July 3, 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 July 3, 2026.
This Delta deal was found by Cheapflights users on 6/29. 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 10/175:15 am
SAT
- ORF
1 stop5h 30m
Delta
Sat 10/175:22 pm
ORF
- SAT
1 stop7h 06m
Delta
Deal found 6/29![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 6/29. 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 7/2811:25 am
SAT
- ORF
2 stops9h 30m
Southwest
Tue 8/46:15 am
ORF
- SAT
1 stop5h 45m
Southwest
Deal found 6/29![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 6/29. 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 8/84:18 pm
SAT
- ORF
1 stop5h 12m
United Airlines
Sat 8/156:15 am
ORF
- SAT
1 stop5h 44m
United Airlines
Deal found 6/29![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 6/30. 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 10/86:22 pm
SAT
- ORF
1 stop5h 11m
Delta
Sat 10/173:13 pm
ORF
- SAT
1 stop5h 26m
Delta
Deal found 6/30![Delta logo]()
$361
This Southwest deal was found by Cheapflights users on 6/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:50 am
SAT
- ORF
2 stops8h 05m
Southwest
Mon 8/106:00 am
ORF
- SAT
2 stops9h 15m
Southwest
Deal found 6/27![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Wed 7/224:18 pm
SAT
- ORF
1 stop5h 12m
United Airlines
Wed 8/56:15 am
ORF
- SAT
1 stop5h 44m
United Airlines
Deal found 6/29![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 7/1. 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 8/97:55 am
SAT
- ORF
1 stop6h 35m
Delta
Thu 8/136:00 am
ORF
- SAT
1 stop5h 34m
Delta
Deal found 7/1![Delta logo]()
$411
This Southwest deal was found by Cheapflights users on 7/1. 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 8/105:00 am
SAT
- ORF
1 stop6h 10m
Southwest
Thu 8/136:00 am
ORF
- SAT
2 stops8h 40m
Southwest
Deal found 7/1![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 6/28. 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.
Wed 8/511:30 am
SAT
- ORF
2 stops8h 20m
Southwest
Sat 8/811:35 am
ORF
- SAT
2 stops9h 45m
Southwest
Deal found 6/28![Southwest logo]()
$434
This Delta deal was found by Cheapflights users on 6/27. 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.
Tue 11/2410:45 am
SAT
- ORF
1 stop5h 14m
Delta
Mon 11/306:05 pm
ORF
- SAT
1 stop7h 23m
Delta
Deal found 6/27![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 7/1. 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 8/215:20 am
SAT
- ORF
1 stop6h 25m
Delta
Sun 8/235:23 am
ORF
- SAT
1 stop6h 46m
Delta
Deal found 7/1![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 7/1. 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 7/313:45 pm
SAT
- ORF
2 stops6h 55m
Southwest
Sun 8/28:05 pm
ORF
- SAT
1 stop6h 05m
Southwest
Deal found 7/1![Southwest logo]()
$452
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated July 3, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/29. 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 7/249:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 7/269:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/29![Frontier logo]()
$319
This Travelocity deal was found by Cheapflights users on 7/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/279:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 7/309:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 7/2![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 6/29. 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 7/2811:25 am
SAT
- ORF
2 stops9h 30m
Southwest
Tue 8/46:15 am
ORF
- SAT
1 stop5h 45m
Southwest
Deal found 6/29![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 6/28. 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.
Wed 7/295:20 am
SAT
- ORF
1 stop6h 25m
Delta
Tue 8/186:23 am
ORF
- SAT
1 stop5h 47m
Delta
Deal found 6/28![Delta logo]()
$344
This Travelocity deal was found by Cheapflights users on 6/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 8/29:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/30![Frontier logo]()
$338
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 8/169:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/28![Frontier logo]()
$288
This Delta deal was found by Cheapflights users on 6/28. 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.
Tue 8/46:25 am
SAT
- ORF
1 stop5h 20m
Delta
Sat 8/155:00 pm
ORF
- SAT
1 stop5h 04m
Delta
Deal found 6/28![Delta logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
SAT
- ORF
2 stops7h 02m
American Airlines
Mon 8/106:17 pm
ORF
- SAT
1 stop7h 31m
American Airlines
Deal found 6/27![American Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 7/1. 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 8/65:20 am
SAT
- ORF
1 stop5h 19m
Delta
Tue 8/115:23 am
ORF
- SAT
1 stop6h 47m
Delta
Deal found 7/1![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 7/1. 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 8/2910:53 am
SAT
- ORF
1 stop5h 15m
Delta
Tue 9/17:50 am
ORF
- SAT
1 stop6h 48m
Delta
Deal found 7/1![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/1. 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.
Sat 8/295:40 am
SAT
- ORF
2 stops7h 30m
Southwest
Tue 9/16:15 pm
ORF
- SAT
1 stop5h 55m
Southwest
Deal found 7/1![Southwest logo]()
$352
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 July 3, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Priceline deal was found by Cheapflights users on 6/30. 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 8/179:51 am
SAT
- ORF
1 stop10h 07m
Frontier
Deal found 6/30![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 8/49:32 pm
SAT
- ORF
2 stops12h 43m
Frontier
Deal found 6/29![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 9/2512:38 pm
SAT
- ORF
3 stops22h 24m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$163
This Priceline deal was found by Cheapflights users on 6/30. 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 9/259:57 am
SAT
- ORF
1 stop6h 18m
Frontier
Deal found 6/30![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 8/1711:30 am
SAT
- ORF
3 stops23h 55m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/289:32 pm
SAT
- ORF
2 stops12h 43m
Frontier
Deal found 7/2![Frontier logo]()
$167
This Priceline deal was found by Cheapflights users on 6/30. 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 7/249:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Deal found 6/30![Frontier logo]()
$170
This Delta deal was found by Cheapflights users on 6/29. 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 8/47:55 am
SAT
- ORF
1 stop6h 35m
Delta
Deal found 6/29![Delta logo]()
$171
This Southwest deal was found by Cheapflights users on 6/30. 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.
Sat 7/257:15 am
SAT
- ORF
1 stop7h 00m
Southwest
Deal found 6/30![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 6/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:30 am
SAT
- ORF
2 stops8h 20m
Southwest
Deal found 6/27![Southwest logo]()
$176
This Frontier deal was found by Cheapflights users on 6/28. 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 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
Deal found 6/28![Frontier logo]()
$181
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 July 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $288 (Frontier) |
One-way from | $150 (Priceline) |
Popular in | January |
Cheapest in | February |
Average price | $446 |
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 July 3, 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 - ORF
SATORF
San Antonio
Sat 10/17
5:15 am-11:45 am
1 stop5h 30m
Norfolk
Sat 10/17
5:22 pm-11:28 pm
1 stop7h 06m
$341
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 7/28
11:25 am-9:55 pm
2 stops9h 30m
Norfolk
Tue 8/4
6:15 am-11:00 am
1 stop5h 45m
$349
Quickest round-trip
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 10/8
6:22 pm-12:33 am
1 stop5h 11m
Norfolk
Sat 10/17
3:13 pm-7:39 pm
1 stop5h 26m
$361
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 8/5
6:50 am-3:55 pm
2 stops8h 05m
Norfolk
Mon 8/10
6:00 am-2:15 pm
2 stops9h 15m
$368
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sun 8/9
7:55 am-3:30 pm
1 stop6h 35m
Norfolk
Thu 8/13
6:00 am-10:34 am
1 stop5h 34m
$411
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Mon 8/10
5:00 am-12:10 pm
1 stop6h 10m
Norfolk
Thu 8/13
6:00 am-1:40 pm
2 stops8h 40m
$416
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 8/8
4:18 pm-10:30 pm
1 stop5h 12m
Norfolk
Sat 8/15
6:15 am-10:59 am
1 stop5h 44m
$431
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 7/22
4:18 pm-10:30 pm
1 stop5h 12m
Norfolk
Wed 8/5
6:15 am-10:59 am
1 stop5h 44m
$434
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 8/5
11:30 am-8:50 pm
2 stops8h 20m
Norfolk
Sat 8/8
11:35 am-8:20 pm
2 stops9h 45m
$434
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 11/24
10:45 am-4:59 pm
1 stop5h 14m
Norfolk
Mon 11/30
6:05 pm-12:28 am
1 stop7h 23m
$447
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.
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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
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SAT-ORF
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 July 3, 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.
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
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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Alternative routes for San Antonio to Chesapeake
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Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Antonio to Chesapeake by cabin class
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 July 3, 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 July 3, 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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$225 | Average$476 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$238 | Average$456 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$463 | FlexibilityNo cancel fee | On-timeN/A |