$130+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
May 16 — May 231
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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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 April 16, 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 April 16, 2026.
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Sun 5/106:34 pm
ORF
- SAT
1 stop22h 42m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
SAT
- ORF
1 stop13h 39m
Multiple Airlines
Sat 8/297:00 am
ORF
- SAT
2 stops10h 13m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Sun 5/315:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Tue 6/912:21 pm
ORF
- SAT
2 stops31h 35m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:54 pm
SAT
- ORF
2 stops14h 01m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/16:00 am
SAT
- ORF
1 stop13h 02m
Multiple Airlines
Fri 5/812:06 pm
ORF
- SAT
2 stops31h 53m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$306
This CheapOair deal was found by Cheapflights users on 4/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/154:22 pm
SAT
- ORF
1 stop27h 18m
Multiple Airlines
Thu 6/1810:09 am
ORF
- SAT
1 stop9h 00m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:09 pm
SAT
- ORF
1 stop26h 52m
Multiple Airlines
Mon 7/2712:21 pm
ORF
- SAT
2 stops31h 35m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:51 pm
SAT
- ORF
2 stops23h 49m
Frontier
Fri 6/269:35 pm
ORF
- SAT
1 stop19h 02m
Frontier
Deal found 4/15![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Sun 5/316:34 pm
ORF
- SAT
1 stop22h 42m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Sun 5/319:12 pm
ORF
- SAT
2 stops24h 02m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:22 pm
SAT
- ORF
1 stop23h 41m
Multiple Airlines
Sat 7/412:06 pm
ORF
- SAT
2 stops22h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:22 pm
SAT
- ORF
1 stop19h 02m
Multiple Airlines
Mon 7/2712:21 pm
ORF
- SAT
2 stops31h 35m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$339
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 April 16, 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 April 16, 2026.
This CheapOair deal was found by Cheapflights users on 4/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/154:22 pm
SAT
- ORF
1 stop27h 18m
Multiple Airlines
Thu 6/1810:09 am
ORF
- SAT
1 stop9h 00m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 4/15. 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.
Sat 6/62:15 pm
SAT
- ORF
1 stop6h 10m
Southwest
Tue 6/93:00 pm
ORF
- SAT
1 stop7h 35m
Southwest
Deal found 4/15![Southwest logo]()
$384
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/64:18 pm
SAT
- ORF
1 stop5h 13m
United Airlines
Tue 6/910:45 am
ORF
- SAT
2 stops10h 05m
United Airlines
Deal found 4/15![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 4/14. 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.
Sun 7/55:25 am
SAT
- ORF
1 stop5h 02m
Delta
Mon 7/277:59 pm
ORF
- SAT
1 stop16h 10m
Delta
Deal found 4/14![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 4/13. 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.
Sun 5/3111:25 am
SAT
- ORF
1 stop10h 55m
Southwest
Tue 6/93:00 pm
ORF
- SAT
1 stop7h 35m
Southwest
Deal found 4/13![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 4/11. 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.
Sun 7/126:19 pm
SAT
- ORF
1 stop5h 26m
Delta
Fri 7/176:20 am
ORF
- SAT
1 stop5h 49m
Delta
Deal found 4/11![Delta logo]()
$447
This United Airlines deal was found by Cheapflights users on 4/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:30 am
SAT
- ORF
2 stops9h 13m
United Airlines
Tue 6/234:57 pm
ORF
- SAT
1 stop7h 00m
United Airlines
Deal found 4/12![United Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 4/11. 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.
Sat 4/252:12 pm
SAT
- ORF
1 stop17h 53m
Multiple Airlines
Tue 4/288:05 am
ORF
- SAT
2 stops40h 46m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 4/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:00 am
SAT
- ORF
1 stop6h 17m
United Airlines
Sat 5/306:15 am
ORF
- SAT
1 stop8h 02m
United Airlines
Deal found 4/12![United Airlines logo]()
$474
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated April 16, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated April 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/16:00 am
SAT
- ORF
1 stop13h 02m
Multiple Airlines
Fri 5/812:06 pm
ORF
- SAT
2 stops31h 53m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/75:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Tue 5/1212:06 pm
ORF
- SAT
2 stops31h 53m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$264
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Sun 5/106:34 pm
ORF
- SAT
1 stop22h 42m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$282
This CheapOair deal was found by Cheapflights users on 4/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:26 pm
SAT
- ORF
2 stops24h 23m
Spirit Airlines
Thu 5/147:44 pm
ORF
- SAT
2 stops21h 32m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/87:54 pm
SAT
- ORF
2 stops14h 01m
Multiple Airlines
Sun 5/106:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 4/12. 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.
Tue 5/126:50 am
SAT
- ORF
1 stop5h 08m
Delta
Wed 5/135:20 am
ORF
- SAT
1 stop5h 32m
Delta
Deal found 4/12![Delta logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:54 pm
SAT
- ORF
2 stops14h 01m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$299
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:26 pm
SAT
- ORF
2 stops24h 23m
Spirit Airlines
Sun 5/177:44 pm
ORF
- SAT
2 stops21h 32m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Sun 5/316:34 pm
ORF
- SAT
1 stop22h 42m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Sun 5/319:12 pm
ORF
- SAT
2 stops24h 02m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Sun 5/315:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Tue 6/912:21 pm
ORF
- SAT
2 stops31h 35m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$290
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 April 16, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated April 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Wed 5/67:54 pm
SAT
- ORF
2 stops14h 17m
Frontier
Deal found 4/12![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:04 pm
SAT
- ORF
1 stop13h 04m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$146
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:54 pm
SAT
- ORF
3 stops45h 55m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:09 pm
SAT
- ORF
2 stops22h 08m
Frontier
Deal found 4/14![Frontier logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$150
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/294:22 pm
SAT
- ORF
1 stop27h 18m
Frontier
Deal found 4/14![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Wed 5/278:59 pm
SAT
- ORF
2 stops22h 18m
Frontier
Deal found 4/16![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:54 pm
SAT
- ORF
2 stops14h 17m
Frontier
Deal found 4/15![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:51 pm
SAT
- ORF
2 stops14h 35m
Frontier
Deal found 4/15![Frontier logo]()
$164
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 April 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $264 (Kiwi.com) |
One-way from | $130 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $399 |
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 April 16, 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
Mon 6/15
4:22 pm-8:40 pm
1 stop27h 18m
Norfolk
Thu 6/18
10:09 am-6:09 pm
1 stop9h 00m
$316
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 6/6
2:15 pm-9:25 pm
1 stop6h 10m
Norfolk
Tue 6/9
3:00 pm-9:35 pm
1 stop7h 35m
$384
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 6/6
4:18 pm-10:31 pm
1 stop5h 13m
Norfolk
Tue 6/9
10:45 am-7:50 pm
2 stops10h 05m
$389
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sun 7/5
5:25 am-11:27 am
1 stop5h 02m
Norfolk
Mon 7/27
7:59 pm-11:09 am
1 stop16h 10m
$416
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sun 5/31
11:25 am-11:20 pm
1 stop10h 55m
Norfolk
Tue 6/9
3:00 pm-9:35 pm
1 stop7h 35m
$440
Quickest round-trip
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sun 7/12
6:19 pm-12:45 am
1 stop5h 26m
Norfolk
Fri 7/17
6:20 am-11:09 am
1 stop5h 49m
$447
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 6/9
5:30 am-3:43 pm
2 stops9h 13m
Norfolk
Tue 6/23
4:57 pm-10:57 pm
1 stop7h 00m
$458
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 4/25
2:12 pm-9:05 am
1 stop17h 53m
Norfolk
Tue 4/28
8:05 am-11:51 pm
2 stops40h 46m
$473
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 5/27
7:00 am-2:17 pm
1 stop6h 17m
Norfolk
Sat 5/30
6:15 am-1:17 pm
1 stop8h 02m
$474
Cheapest one-way
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 5/7
5:26 pm-5:39 pm
1 stop23h 13m
$147
Showing 1-10 of 18 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 April 10, 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.
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 April 16, 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
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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San Antonio and Chesapeake flights
Browse other San Antonio and Chesapeake flight options. Last updated on April 16, 2026.
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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 April 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$334 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$238 | Average$461 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$238 | Average$485 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$456 | FlexibilityNo cancel fee | On-timeN/A |