$123+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Aug 28 — Sep 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 29, 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 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:51 am
SAT
- ORF
1 stop29h 20m
Frontier
Mon 8/311:20 pm
ORF
- SAT
2 stops31h 11m
Frontier
Deal found 7/26![Frontier logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:26 pm
SAT
- ORF
2 stops14h 59m
Frontier
Sun 8/305:06 pm
ORF
- SAT
1 stop16h 50m
Frontier
Deal found 7/25![Frontier logo]()
$353
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:50 am
SAT
- ORF
1 stop5h 05m
Southwest
Sat 8/229:55 am
ORF
- SAT
1 stop7h 50m
Southwest
Deal found 7/25![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:30 am
SAT
- ORF
2 stops7h 47m
United Airlines
Sat 8/225:02 pm
ORF
- SAT
1 stop6h 49m
United Airlines
Deal found 7/25![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
SAT
- ORF
1 stop9h 55m
Southwest
Mon 8/1712:50 pm
ORF
- SAT
1 stop9h 35m
Southwest
Deal found 7/25![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Sat 9/54:40 pm
SAT
- ORF
1 stop5h 35m
American Airlines
Mon 9/76:00 am
ORF
- SAT
1 stop6h 32m
American Airlines
Deal found 7/24![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 7/24. 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 8/1512:37 pm
SAT
- ORF
1 stop9h 36m
Delta
Tue 8/187:50 am
ORF
- SAT
1 stop6h 48m
Delta
Deal found 7/24![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:20 pm
SAT
- ORF
2 stops8h 35m
Southwest
Mon 8/316:00 am
ORF
- SAT
2 stops7h 50m
Southwest
Deal found 7/26![Southwest logo]()
$366
This Trip.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:51 am
SAT
- ORF
1 stop10h 07m
Frontier
Fri 8/1410:02 pm
ORF
- SAT
1 stop18h 39m
Frontier
Deal found 7/26![Frontier logo]()
$369
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Sat 8/1512:29 pm
SAT
- ORF
1 stop5h 24m
American Airlines
Tue 8/184:00 pm
ORF
- SAT
2 stops7h 00m
American Airlines
Deal found 7/24![American Airlines logo]()
$377
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 29, 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 29, 2026.
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
SAT
- ORF
1 stop9h 55m
Southwest
Mon 8/1712:50 pm
ORF
- SAT
1 stop9h 35m
Southwest
Deal found 7/25![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 7/27. 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.
Fri 11/65:00 pm
SAT
- ORF
1 stop6h 45m
Delta
Tue 11/103:00 pm
ORF
- SAT
1 stop5h 38m
Delta
Deal found 7/27![Delta logo]()
$388
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:07 am
SAT
- ORF
1 stop6h 08m
American Airlines
Tue 11/1010:20 am
ORF
- SAT
2 stops7h 42m
American Airlines
Deal found 7/28![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:00 pm
SAT
- ORF
1 stop7h 41m
United Airlines
Sat 9/125:02 pm
ORF
- SAT
1 stop6h 49m
United Airlines
Deal found 7/25![United Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:20 pm
SAT
- ORF
2 stops8h 35m
Southwest
Mon 8/316:00 am
ORF
- SAT
2 stops9h 15m
Southwest
Deal found 7/25![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:15 pm
SAT
- ORF
1 stop4h 59m
Delta
Sat 1/25:30 am
ORF
- SAT
1 stop5h 24m
Delta
Deal found 7/26![Delta logo]()
$406
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:30 am
SAT
- ORF
2 stops7h 45m
United Airlines
Wed 9/96:02 am
ORF
- SAT
2 stops10h 58m
United Airlines
Deal found 7/28![United Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:10 am
SAT
- ORF
2 stops9h 25m
Southwest
Sun 8/303:15 pm
ORF
- SAT
2 stops9h 15m
Southwest
Deal found 7/25![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:15 pm
SAT
- ORF
1 stop4h 59m
Delta
Sun 12/277:40 pm
ORF
- SAT
1 stop5h 48m
Delta
Deal found 7/26![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 7/27. 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.
Thu 8/132:15 pm
SAT
- ORF
1 stop6h 40m
Southwest
Thu 8/2712:50 pm
ORF
- SAT
1 stop7h 20m
Southwest
Deal found 7/27![Southwest logo]()
$466
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated July 29, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:51 am
SAT
- ORF
1 stop10h 07m
Frontier
Fri 8/1410:02 pm
ORF
- SAT
1 stop18h 39m
Frontier
Deal found 7/26![Frontier logo]()
$369
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
SAT
- ORF
1 stop9h 55m
Southwest
Mon 8/1712:50 pm
ORF
- SAT
1 stop9h 35m
Southwest
Deal found 7/25![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 7/24. 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 8/1512:37 pm
SAT
- ORF
1 stop9h 36m
Delta
Tue 8/187:50 am
ORF
- SAT
1 stop6h 48m
Delta
Deal found 7/24![Delta logo]()
$365
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Sat 8/1512:29 pm
SAT
- ORF
1 stop5h 24m
American Airlines
Tue 8/184:00 pm
ORF
- SAT
2 stops7h 00m
American Airlines
Deal found 7/24![American Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:30 am
SAT
- ORF
1 stop6h 47m
United Airlines
Mon 8/173:00 pm
ORF
- SAT
2 stops8h 50m
United Airlines
Deal found 7/25![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:50 am
SAT
- ORF
1 stop5h 05m
Southwest
Sat 8/229:55 am
ORF
- SAT
1 stop7h 50m
Southwest
Deal found 7/25![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:30 am
SAT
- ORF
2 stops7h 47m
United Airlines
Sat 8/225:02 pm
ORF
- SAT
1 stop6h 49m
United Airlines
Deal found 7/25![United Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Fri 8/217:00 am
SAT
- ORF
1 stop6h 02m
American Airlines
Tue 8/251:20 pm
ORF
- SAT
1 stop8h 37m
American Airlines
Deal found 7/24![American Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:51 am
SAT
- ORF
1 stop29h 20m
Frontier
Mon 8/311:20 pm
ORF
- SAT
2 stops31h 11m
Frontier
Deal found 7/26![Frontier logo]()
$344
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:20 pm
SAT
- ORF
2 stops8h 35m
Southwest
Mon 8/316:00 am
ORF
- SAT
2 stops7h 50m
Southwest
Deal found 7/26![Southwest logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:26 pm
SAT
- ORF
2 stops14h 59m
Frontier
Sun 8/305:06 pm
ORF
- SAT
1 stop16h 50m
Frontier
Deal found 7/25![Frontier logo]()
$353
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 29, 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 29, 2026.
This Expedia deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:03 am
SAT
- ORF
1 stop7h 45m
Frontier
Deal found 7/26![Frontier logo]()
$123
This Priceline deal was found by Cheapflights users on 7/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:05 am
SAT
- ORF
1 stop7h 43m
Frontier
Deal found 7/27![Frontier logo]()
$141
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:57 am
SAT
- ORF
1 stop6h 18m
Frontier
Deal found 7/25![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/119:25 am
SAT
- ORF
2 stops25h 37m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 7/24. 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 9/1111:50 am
SAT
- ORF
1 stop5h 05m
Southwest
Deal found 7/24![Southwest logo]()
$179
This Priceline deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:51 am
SAT
- ORF
1 stop10h 07m
Frontier
Deal found 7/26![Frontier logo]()
$180
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:00 pm
SAT
- ORF
2 stops9h 54m
United Airlines
Deal found 7/26![United Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:26 pm
SAT
- ORF
2 stops14h 59m
Frontier
Deal found 7/28![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:26 pm
SAT
- ORF
2 stops14h 59m
Frontier
Deal found 7/27![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/238:26 pm
SAT
- ORF
2 stops14h 59m
Frontier
Deal found 7/24![Frontier logo]()
$190
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $344 (Kiwi.com) |
One-way from | $123 (Expedia) |
Popular in | January |
Cheapest in | February |
Average price | $472 |
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 29, 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 8/15
6:00 am-4:55 pm
1 stop9h 55m
Norfolk
Mon 8/17
12:50 pm-9:25 pm
1 stop9h 35m
$361
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Mon 8/24
12:20 pm-9:55 pm
2 stops8h 35m
Norfolk
Mon 8/31
6:00 am-2:15 pm
2 stops9h 15m
$366
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Fri 11/6
5:00 pm-12:45 am
1 stop6h 45m
Norfolk
Tue 11/10
3:00 pm-7:38 pm
1 stop5h 38m
$388
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Fri 11/6
6:07 am-1:15 pm
1 stop6h 08m
Norfolk
Tue 11/10
10:20 am-5:02 pm
2 stops7h 42m
$393
Quickest round-trip
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Mon 12/21
6:15 pm-12:14 am
1 stop4h 59m
Norfolk
Sat 1/2
5:30 am-9:54 am
1 stop5h 24m
$406
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 8/27
11:10 am-9:35 pm
2 stops9h 25m
Norfolk
Sun 8/30
3:15 pm-11:30 pm
2 stops9h 15m
$417
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 9/9
1:00 pm-9:41 pm
1 stop7h 41m
Norfolk
Sat 9/12
5:02 pm-10:51 pm
1 stop6h 49m
$445
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 8/25
5:30 am-2:15 pm
2 stops7h 45m
Norfolk
Wed 9/9
6:02 am-4:00 pm
2 stops10h 58m
$456
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 12/19
6:15 pm-12:14 am
1 stop4h 59m
Norfolk
Sun 12/27
7:40 pm-12:28 am
1 stop5h 48m
$457
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 8/13
2:15 pm-9:55 pm
1 stop6h 40m
Norfolk
Thu 8/27
12:50 pm-7:10 pm
1 stop7h 20m
$466
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.
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?
Airfare is typical for this route at the moment.
San Antonio to Chesapeake flights typically cost between $321 and $491 in August.The cheapest round-trip price found within the last 5 days was $344 on Frontier (Aug 24-Aug 31).
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 29, 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
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from San Antonio
Popular flights
Top destinations
Alternative routes for San Antonio to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
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 29, 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 29, 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$288 | Average$464 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$298 | Average$481 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$312 | Average$456 | FlexibilityNo cancel fee | On-time63% |