$160+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Jul 4 — Jul 111
Round-trip
1 adult, Economy
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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 June 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 June 4, 2026.
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/69:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 7/99:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/2![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 7/129:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/4![Frontier logo]()
$310
This Delta deal was found by Cheapflights users on 6/1. 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 7/285:20 am
SAT
- ORF
1 stop6h 25m
Delta
Tue 8/116:14 pm
ORF
- SAT
1 stop7h 14m
Delta
Deal found 6/1![Delta logo]()
$320
This American Airlines deal was found by Cheapflights users on 5/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:10 pm
SAT
- ORF
1 stop6h 13m
American Airlines
Tue 8/116:17 pm
ORF
- SAT
1 stop7h 31m
American Airlines
Deal found 5/31![American Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:53 pm
SAT
- ORF
2 stops30h 00m
Multiple Airlines
Sun 8/29:34 pm
ORF
- SAT
1 stop12h 22m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$347
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 7/239:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/2![Frontier logo]()
$350
This Frontier deal was found by Cheapflights users on 6/4. 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 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
Sun 7/199:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/4![Frontier logo]()
$359
This Booking.com deal was found by Cheapflights users on 6/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/194:22 pm
SAT
- ORF
1 stop25h 18m
Frontier
Sun 6/219:35 pm
ORF
- SAT
1 stop19h 02m
Frontier
Deal found 6/1![Frontier logo]()
$363
This CheapOair deal was found by Cheapflights users on 6/3. 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.
Fri 6/264:22 pm
SAT
- ORF
1 stop25h 18m
Frontier
Thu 7/29:35 pm
ORF
- SAT
1 stop19h 02m
Frontier
Deal found 6/3![Frontier logo]()
$368
This Booking.com deal was found by Cheapflights users on 6/4. 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 Booking.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 stop25h 18m
Frontier
Sun 7/59:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/4![Frontier logo]()
$372
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 June 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 June 4, 2026.
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:20 am
SAT
- ORF
1 stop6h 25m
Delta
Tue 8/115:23 am
ORF
- SAT
1 stop5h 25m
Delta
Deal found 5/31![Delta logo]()
$320
This Southwest deal was found by Cheapflights users on 6/1. 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.
Tue 7/145:15 am
SAT
- ORF
1 stop5h 45m
Southwest
Wed 7/224:30 pm
ORF
- SAT
1 stop6h 10m
Southwest
Deal found 6/1![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 6/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:30 am
SAT
- ORF
2 stops7h 47m
United Airlines
Wed 8/56:05 am
ORF
- SAT
1 stop5h 54m
United Airlines
Deal found 6/2![United Airlines logo]()
$478
This CheapOair deal was found by Cheapflights users on 6/4. 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.
Mon 8/39:51 am
SAT
- ORF
1 stop9h 48m
Multiple Airlines
Sat 8/87:00 am
ORF
- SAT
2 stops10h 58m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:50 am
SAT
- ORF
1 stop5h 30m
Southwest
Tue 7/144:30 pm
ORF
- SAT
2 stops8h 15m
Southwest
Deal found 6/4![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 6/1. 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 7/141:25 pm
SAT
- ORF
2 stops9h 19m
United Airlines
Wed 7/226:05 am
ORF
- SAT
1 stop5h 54m
United Airlines
Deal found 6/1![United Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 6/1. 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.
Thu 7/165:10 am
SAT
- ORF
1 stop5h 30m
Southwest
Thu 7/234:30 pm
ORF
- SAT
1 stop7h 55m
Southwest
Deal found 6/1![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:19 pm
SAT
- ORF
1 stop5h 26m
Delta
Sat 7/44:54 pm
ORF
- SAT
1 stop6h 14m
Delta
Deal found 6/4![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 6/1. 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 7/133:45 pm
SAT
- ORF
2 stops6h 55m
Southwest
Thu 7/164:30 pm
ORF
- SAT
1 stop7h 55m
Southwest
Deal found 6/1![Southwest logo]()
$452
This Southwest deal was found by Cheapflights users on 6/1. 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 7/173:45 pm
SAT
- ORF
2 stops6h 55m
Southwest
Wed 7/223:40 pm
ORF
- SAT
2 stops8h 20m
Southwest
Deal found 6/1![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 6/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/203:40 pm
SAT
- ORF
2 stops7h 00m
Southwest
Thu 7/234:30 pm
ORF
- SAT
2 stops7h 25m
Southwest
Deal found 6/2![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 6/3. 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.
Fri 6/263:45 pm
SAT
- ORF
1 stop6h 50m
Southwest
Thu 7/24:30 pm
ORF
- SAT
2 stops7h 20m
Southwest
Deal found 6/3![Southwest logo]()
$492
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated June 4, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/194:22 pm
SAT
- ORF
1 stop25h 18m
Frontier
Sun 6/219:35 pm
ORF
- SAT
1 stop19h 02m
Frontier
Deal found 6/1![Frontier logo]()
$363
This CheapOair deal was found by Cheapflights users on 6/3. 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.
Fri 6/264:22 pm
SAT
- ORF
1 stop25h 18m
Frontier
Thu 7/29:35 pm
ORF
- SAT
1 stop19h 02m
Frontier
Deal found 6/3![Frontier logo]()
$368
This Booking.com deal was found by Cheapflights users on 6/4. 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 Booking.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 stop25h 18m
Frontier
Sun 7/59:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/4![Frontier logo]()
$372
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/69:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 7/99:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/2![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Sun 7/129:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/4![Frontier logo]()
$310
This Frontier deal was found by Cheapflights users on 6/4. 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 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
Sun 7/199:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/4![Frontier logo]()
$359
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Thu 7/239:34 pm
ORF
- SAT
1 stop12h 22m
Frontier
Deal found 6/2![Frontier logo]()
$350
This Delta deal was found by Cheapflights users on 6/1. 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 7/285:20 am
SAT
- ORF
1 stop6h 25m
Delta
Tue 8/116:14 pm
ORF
- SAT
1 stop7h 14m
Delta
Deal found 6/1![Delta logo]()
$320
This American Airlines deal was found by Cheapflights users on 5/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:10 pm
SAT
- ORF
1 stop6h 13m
American Airlines
Tue 8/116:17 pm
ORF
- SAT
1 stop7h 31m
American Airlines
Deal found 5/31![American Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:53 pm
SAT
- ORF
2 stops30h 00m
Multiple Airlines
Sun 8/29:34 pm
ORF
- SAT
1 stop12h 22m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$347
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 June 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 June 4, 2026.
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Deal found 6/4![Frontier logo]()
$160
This Priceline deal was found by Cheapflights users on 6/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:51 am
SAT
- ORF
1 stop9h 48m
Frontier
Deal found 6/2![Frontier logo]()
$161
This Frontier deal was found by Cheapflights users on 6/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:57 am
SAT
- ORF
1 stop6h 18m
Frontier
Deal found 6/2![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Mon 9/2812:38 pm
SAT
- ORF
2 stops28h 05m
Breeze Airways
Deal found 6/2![Breeze Airways logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 5/31. 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.
Mon 9/2112:38 pm
SAT
- ORF
2 stops28h 05m
Breeze Airways
Deal found 5/31![Breeze Airways logo]()
$183
This Booking.com deal was found by Cheapflights users on 6/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/224:22 pm
SAT
- ORF
1 stop25h 18m
Frontier
Deal found 6/3![Frontier logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:01 am
SAT
- ORF
1 stop5h 33m
American Airlines
Deal found 6/4![American Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/29:32 pm
SAT
- ORF
2 stops46h 07m
Frontier
Deal found 6/4![Frontier logo]()
$203
This Mytrip deal was found by Cheapflights users on 5/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:57 am
SAT
- ORF
1 stop6h 18m
Frontier
Deal found 5/31![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:55 am
SAT
- ORF
2 stops24h 31m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$205
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 June 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $308 (Expedia) |
One-way from | $160 (Frontier) |
Popular in | January |
Cheapest in | August |
Average price | $449 |
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 June 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 7/28
5:20 am-12:45 pm
1 stop6h 25m
Norfolk
Tue 8/11
5:23 am-9:48 am
1 stop5h 25m
$320
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 7/14
5:15 am-12:00 pm
1 stop5h 45m
Norfolk
Wed 7/22
4:30 pm-9:40 pm
1 stop6h 10m
$383
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 7/7
11:50 am-6:20 pm
1 stop5h 30m
Norfolk
Tue 7/14
4:30 pm-11:45 pm
2 stops8h 15m
$388
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 7/16
5:10 am-11:40 am
1 stop5h 30m
Norfolk
Thu 7/23
4:30 pm-11:25 pm
1 stop7h 55m
$447
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Mon 7/13
3:45 pm-11:40 pm
2 stops6h 55m
Norfolk
Thu 7/16
4:30 pm-11:25 pm
1 stop7h 55m
$452
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Fri 7/17
3:45 pm-11:40 pm
2 stops6h 55m
Norfolk
Wed 7/22
3:40 pm-11:00 pm
2 stops8h 20m
$457
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Mon 7/20
3:40 pm-11:40 pm
2 stops7h 00m
Norfolk
Thu 7/23
4:30 pm-10:55 pm
2 stops7h 25m
$477
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 8/4
5:30 am-2:17 pm
2 stops7h 47m
Norfolk
Wed 8/5
6:05 am-10:59 am
1 stop5h 54m
$478
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 7/14
1:25 pm-11:44 pm
2 stops9h 19m
Norfolk
Wed 7/22
6:05 am-10:59 am
1 stop5h 54m
$478
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Fri 6/26
3:45 pm-11:35 pm
1 stop6h 50m
Norfolk
Thu 7/2
4:30 pm-10:50 pm
2 stops7h 20m
$492
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from San Antonio to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from San Antonio with our price prediction graph.
SAT-ORF
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Antonio to Chesapeake
SAT-C6E
SAT-ORF
How much does it cost to fly round-trip from San Antonio to Chesapeake?
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 June 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.
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Related info for your journey
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San Antonio and Chesapeake flights
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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 June 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$238 | Average$471 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$238 | Average$477 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$466 | FlexibilityNo cancel fee | On-timeN/A |