$132+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
May 4 — May 111
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 4, 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 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 4/292:12 pm
SAT
- ORF
1 stop28h 34m
Multiple Airlines
Mon 5/412:31 pm
ORF
- SAT
2 stops31h 28m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
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 4/2![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 4/3. 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
2 stops14h 17m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$287
This CheapOair deal was found by Cheapflights users on 4/4. 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 4/4![Spirit Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/97:54 pm
SAT
- ORF
2 stops14h 17m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Sat 4/186:30 pm
SAT
- ORF
2 stops15h 02m
Multiple Airlines
Sat 5/27:16 pm
ORF
- SAT
1 stop19h 01m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/117:54 pm
SAT
- ORF
2 stops14h 17m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 4/3. 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
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/137:54 pm
SAT
- ORF
2 stops25h 52m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/245:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Fri 5/2912:06 pm
ORF
- SAT
2 stops31h 53m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/105:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Mon 5/189:12 pm
ORF
- SAT
2 stops22h 47m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$326
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 4, 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 4, 2026.
This Delta deal was found by Cheapflights users on 4/1. 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.
Tue 6/96:45 am
SAT
- ORF
1 stop7h 47m
Delta
Tue 6/236:05 am
ORF
- SAT
1 stop5h 30m
Delta
Deal found 4/1![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 4/3. 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 6/156:25 am
SAT
- ORF
1 stop8h 25m
Southwest
Thu 6/184:30 pm
ORF
- SAT
1 stop7h 50m
Southwest
Deal found 4/3![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 4/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:15 am
SAT
- ORF
1 stop5h 56m
United Airlines
Wed 4/299:45 am
ORF
- SAT
1 stop7h 24m
United Airlines
Deal found 4/1![United Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 4/3. 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 5/94:15 pm
SAT
- ORF
1 stop6h 05m
Delta
Sat 5/1611:43 am
ORF
- SAT
1 stop5h 04m
Delta
Deal found 4/3![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 4/3. 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 5/910:52 am
SAT
- ORF
1 stop5h 20m
Delta
Tue 5/192:03 pm
ORF
- SAT
1 stop5h 20m
Delta
Deal found 4/3![Delta logo]()
$397
This KAYAK deal was found by Cheapflights users on 3/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:30 am
SAT
- ORF
3 stops10h 20m
Southwest
Thu 4/302:30 pm
ORF
- SAT
2 stops10h 00m
Southwest
Deal found 3/30![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 4/3. 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 stops10h 33m
United Airlines
Tue 6/236:00 am
ORF
- SAT
1 stop7h 12m
United Airlines
Deal found 4/3![United Airlines logo]()
$458
This Delta deal was found by Cheapflights users on 4/3. 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 6/276:45 am
SAT
- ORF
1 stop4h 58m
Delta
Wed 7/15:15 am
ORF
- SAT
1 stop5h 37m
Delta
Deal found 4/3![Delta logo]()
$405
This United Airlines deal was found by Cheapflights users on 4/3. 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 5/122:25 pm
SAT
- ORF
2 stops8h 07m
United Airlines
Wed 5/205:14 pm
ORF
- SAT
1 stop6h 40m
United Airlines
Deal found 4/3![United Airlines logo]()
$458
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated April 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Sat 4/186:30 pm
SAT
- ORF
2 stops15h 02m
Multiple Airlines
Sat 5/27:16 pm
ORF
- SAT
1 stop19h 01m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 4/292:12 pm
SAT
- ORF
1 stop28h 34m
Multiple Airlines
Mon 5/412:31 pm
ORF
- SAT
2 stops31h 28m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
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 4/2![Multiple Airlines logo]()
$281
This CheapOair deal was found by Cheapflights users on 4/4. 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 4/4![Spirit Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/97:54 pm
SAT
- ORF
2 stops14h 17m
Multiple Airlines
Thu 5/146:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/105:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Thu 5/1412:06 pm
ORF
- SAT
2 stops31h 53m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/117:54 pm
SAT
- ORF
2 stops14h 17m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 4/3. 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
2 stops14h 17m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/137:54 pm
SAT
- ORF
2 stops25h 52m
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 4/3. 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
Multiple Airlines
Sun 5/176:34 pm
ORF
- SAT
1 stop22h 42m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/245:26 pm
SAT
- ORF
1 stop23h 13m
Multiple Airlines
Fri 5/2912:06 pm
ORF
- SAT
2 stops31h 53m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$323
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 4, 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 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Tue 6/237:51 pm
SAT
- ORF
2 stops14h 35m
Frontier
Deal found 3/30![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/3![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 3/31![Frontier logo]()
$142
This Priceline deal was found by Cheapflights users on 3/30. 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.
Thu 6/256:00 am
SAT
- ORF
1 stop9h 53m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$146
This CheapOair deal was found by Cheapflights users on 3/31. 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 3/31![Spirit Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Sun 6/218:56 pm
SAT
- ORF
2 stops37h 30m
Frontier
Deal found 3/30![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Wed 6/247:51 pm
SAT
- ORF
2 stops14h 35m
Frontier
Deal found 3/30![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Tue 6/308:56 pm
SAT
- ORF
2 stops13h 30m
Frontier
Deal found 3/30![Frontier logo]()
$175
This CheapOair deal was found by Cheapflights users on 4/3. 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 5/215:26 pm
SAT
- ORF
1 stop23h 13m
Spirit Airlines
Deal found 4/3![Spirit Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 3/30. 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.
Tue 6/237:00 am
SAT
- ORF
1 stop7h 50m
Southwest
Deal found 3/30![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/163:00 pm
SAT
- ORF
2 stops50h 21m
Frontier
Deal found 3/30![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/163:00 pm
SAT
- ORF
3 stops25h 04m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$185
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 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (Kiwi.com) |
One-way from | $132 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $393 |
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 4, 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
Tue 6/9
6:45 am-3:32 pm
1 stop7h 47m
Norfolk
Tue 6/23
6:05 am-10:35 am
1 stop5h 30m
$363
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 5/9
4:15 pm-11:20 pm
1 stop6h 05m
Norfolk
Sat 5/16
11:43 am-3:47 pm
1 stop5h 04m
$397
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 5/9
10:52 am-5:12 pm
1 stop5h 20m
Norfolk
Tue 5/19
2:03 pm-6:23 pm
1 stop5h 20m
$397
Quickest round-trip
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 6/27
6:45 am-12:43 pm
1 stop4h 58m
Norfolk
Wed 7/1
5:15 am-9:52 am
1 stop5h 37m
$405
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Mon 6/15
6:25 am-3:50 pm
1 stop8h 25m
Norfolk
Thu 6/18
4:30 pm-11:20 pm
1 stop7h 50m
$447
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 4/28
6:30 am-5:50 pm
3 stops10h 20m
Norfolk
Thu 4/30
2:30 pm-11:30 pm
2 stops10h 00m
$448
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 4/28
7:15 am-2:11 pm
1 stop5h 56m
Norfolk
Wed 4/29
9:45 am-4:09 pm
1 stop7h 24m
$453
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 6/9
5:30 am-5:03 pm
2 stops10h 33m
Norfolk
Tue 6/23
6:00 am-12:12 pm
1 stop7h 12m
$458
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 5/12
2:25 pm-11:32 pm
2 stops8h 07m
Norfolk
Wed 5/20
5:14 pm-10:54 pm
1 stop6h 40m
$458
Cheapest one-way
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 6/25
6:00 am-4:53 pm
1 stop9h 53m
$146
Showing 1-10 of 17 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
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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 2, 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, November is the cheapest month in which you can book a flight from San Antonio to Chesapeake (average of $143). Flying from San Antonio to Chesapeake in April is currently the most expensive (average of $256). 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.
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 4, 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.
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
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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San Antonio and Chesapeake flights
Browse other San Antonio and Chesapeake flight options. Last updated on April 4, 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 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$334 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$238 | Average$463 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$238 | Average$471 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$298 | Average$454 | FlexibilityNo cancel fee | On-timeN/A |