$122+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Jun 18 — Jun 251
Round-trip
1 adult, Economy
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Find cheap flights from San Antonio to Chesapeake with Cheapflights
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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 May 19, 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 May 19, 2026.
This Booking.com deal was found by Cheapflights users on 5/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/104:26 pm
SAT
- ORF
1 stop27h 13m
Frontier
Sun 7/129:35 pm
ORF
- SAT
1 stop19h 06m
Frontier
Deal found 5/14![Frontier logo]()
$333
This Trip.com deal was found by Cheapflights users on 5/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:59 pm
SAT
- ORF
2 stops13h 12m
Frontier
Tue 6/912:21 pm
ORF
- SAT
2 stops31h 35m
Frontier
Deal found 5/16![Frontier logo]()
$369
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 6/2411:50 am
SAT
- ORF
1 stop5h 30m
Southwest
Tue 6/303:00 pm
ORF
- SAT
1 stop7h 35m
Southwest
Deal found 5/15![Southwest logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Mon 8/34:26 pm
SAT
- ORF
1 stop27h 13m
Multiple Airlines
Sat 8/87:00 am
ORF
- SAT
2 stops10h 13m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:20 pm
SAT
- ORF
2 stops8h 15m
Southwest
Tue 7/213:00 pm
ORF
- SAT
2 stops8h 00m
Southwest
Deal found 5/16![Southwest logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 5/16. 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.
Tue 7/77:51 pm
SAT
- ORF
2 stops23h 48m
Frontier
Fri 7/109:35 pm
ORF
- SAT
1 stop19h 06m
Frontier
Deal found 5/16![Frontier logo]()
$399
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:52 pm
SAT
- ORF
1 stop4h 51m
American Airlines
Mon 6/155:05 am
ORF
- SAT
1 stop5h 05m
American Airlines
Deal found 5/14![American Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 5/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:52 pm
SAT
- ORF
1 stop4h 48m
American Airlines
Tue 7/76:23 am
ORF
- SAT
1 stop8h 07m
American Airlines
Deal found 5/16![American Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:52 pm
SAT
- ORF
1 stop4h 48m
American Airlines
Wed 7/151:26 pm
ORF
- SAT
1 stop8h 14m
American Airlines
Deal found 5/17![American Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/173:15 pm
SAT
- ORF
1 stop6h 20m
Southwest
Mon 6/227:15 pm
ORF
- SAT
1 stop5h 50m
Southwest
Deal found 5/16![Southwest logo]()
$415
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 May 19, 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 May 19, 2026.
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:15 pm
SAT
- ORF
1 stop6h 20m
Southwest
Tue 6/306:05 am
ORF
- SAT
1 stop5h 40m
Southwest
Deal found 5/16![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:30 am
SAT
- ORF
2 stops7h 45m
United Airlines
Mon 8/175:02 pm
ORF
- SAT
1 stop6h 49m
United Airlines
Deal found 5/13![United Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:05 am
SAT
- ORF
1 stop5h 47m
Delta
Fri 8/146:14 pm
ORF
- SAT
1 stop7h 14m
Delta
Deal found 5/13![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 5/17. 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 6/271:40 pm
SAT
- ORF
1 stop6h 47m
American Airlines
Wed 7/16:48 pm
ORF
- SAT
1 stop6h 11m
American Airlines
Deal found 5/17![American Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:15 am
SAT
- ORF
1 stop8h 10m
Southwest
Mon 6/226:10 pm
ORF
- SAT
1 stop6h 10m
Southwest
Deal found 5/16![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/233:15 pm
SAT
- ORF
1 stop6h 20m
Southwest
Mon 6/294:30 pm
ORF
- SAT
1 stop7h 50m
Southwest
Deal found 5/16![Southwest logo]()
$415
This United Airlines deal was found by Cheapflights users on 5/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:18 pm
SAT
- ORF
1 stop5h 12m
United Airlines
Tue 6/306:05 am
ORF
- SAT
2 stops11h 24m
United Airlines
Deal found 5/16![United Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 5/17. 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 6/303:15 pm
SAT
- ORF
1 stop6h 20m
Southwest
Sat 7/42:50 pm
ORF
- SAT
1 stop6h 15m
Southwest
Deal found 5/17![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 5/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/101:50 pm
SAT
- ORF
2 stops8h 45m
Southwest
Sun 7/128:05 pm
ORF
- SAT
1 stop6h 00m
Southwest
Deal found 5/14![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 5/15. 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.
Thu 6/113:40 pm
SAT
- ORF
2 stops6h 55m
Southwest
Mon 6/153:30 pm
ORF
- SAT
1 stop9h 35m
Southwest
Deal found 5/15![Southwest logo]()
$478
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated May 19, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 5/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:59 pm
SAT
- ORF
2 stops13h 12m
Frontier
Tue 6/912:21 pm
ORF
- SAT
2 stops31h 35m
Frontier
Deal found 5/16![Frontier logo]()
$369
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:52 pm
SAT
- ORF
1 stop4h 51m
American Airlines
Mon 6/155:05 am
ORF
- SAT
1 stop5h 05m
American Airlines
Deal found 5/14![American Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:52 pm
SAT
- ORF
1 stop4h 51m
American Airlines
Mon 6/155:05 am
ORF
- SAT
1 stop5h 05m
American Airlines
Deal found 5/14![American Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:20 pm
SAT
- ORF
2 stops8h 15m
Southwest
Mon 6/227:15 pm
ORF
- SAT
1 stop5h 50m
Southwest
Deal found 5/16![Southwest logo]()
$420
This Southwest deal was found by Cheapflights users on 5/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/173:15 pm
SAT
- ORF
1 stop6h 20m
Southwest
Mon 6/227:15 pm
ORF
- SAT
1 stop5h 50m
Southwest
Deal found 5/16![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 6/2411:50 am
SAT
- ORF
1 stop5h 30m
Southwest
Tue 6/303:00 pm
ORF
- SAT
1 stop7h 35m
Southwest
Deal found 5/15![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 5/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:01 pm
SAT
- ORF
2 stops8h 41m
United Airlines
Tue 6/305:00 pm
ORF
- SAT
1 stop6h 57m
United Airlines
Deal found 5/14![United Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 6/2411:50 am
SAT
- ORF
1 stop5h 30m
Southwest
Mon 6/296:10 pm
ORF
- SAT
2 stops7h 50m
Southwest
Deal found 5/15![Southwest logo]()
$430
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/271:40 pm
SAT
- ORF
1 stop6h 47m
American Airlines
Wed 7/12:27 pm
ORF
- SAT
1 stop7h 09m
American Airlines
Deal found 5/14![American Airlines logo]()
$438
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 May 19, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
This Trip.com deal was found by Cheapflights users on 5/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:51 pm
SAT
- ORF
2 stops14h 30m
Frontier
Deal found 5/15![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 5/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:54 pm
SAT
- ORF
2 stops14h 17m
Frontier
Deal found 5/15![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/97:51 pm
SAT
- ORF
2 stops21h 49m
Frontier
Deal found 5/18![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/107:51 pm
SAT
- ORF
2 stops14h 35m
Frontier
Deal found 5/18![Frontier logo]()
$171
This American Airlines deal was found by Cheapflights users on 5/18. 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 7/78:00 am
SAT
- ORF
1 stop4h 49m
American Airlines
Deal found 5/18![American Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Wed 6/174:53 pm
SAT
- ORF
3 stops41h 33m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:52 pm
SAT
- ORF
1 stop4h 51m
American Airlines
Deal found 5/14![American Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Wed 6/177:51 pm
SAT
- ORF
2 stops23h 49m
Frontier
Deal found 5/14![Frontier logo]()
$213
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:00 am
SAT
- ORF
1 stop4h 46m
American Airlines
Deal found 5/14![American Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Wed 5/277:54 pm
SAT
- ORF
2 stops23h 23m
Frontier
Deal found 5/14![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Sun 6/219:55 am
SAT
- ORF
2 stops24h 31m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$234
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 May 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $333 (Booking.com) |
One-way from | $122 (Trip.com) |
Popular in | January |
Cheapest in | August |
Average price | $486 |
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 May 19, 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
Quickest round-trip
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 6/24
3:15 pm-10:35 pm
1 stop6h 20m
Norfolk
Tue 6/30
6:05 am-10:45 am
1 stop5h 40m
$383
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 8/13
5:30 am-2:15 pm
2 stops7h 45m
Norfolk
Mon 8/17
5:02 pm-10:51 pm
1 stop6h 49m
$410
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 6/16
5:15 am-2:25 pm
1 stop8h 10m
Norfolk
Mon 6/22
6:10 pm-11:20 pm
1 stop6h 10m
$415
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 6/23
3:15 pm-10:35 pm
1 stop6h 20m
Norfolk
Mon 6/29
4:30 pm-11:20 pm
1 stop7h 50m
$415
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Tue 6/30
3:15 pm-10:35 pm
1 stop6h 20m
Norfolk
Sat 7/4
2:50 pm-8:05 pm
1 stop6h 15m
$415
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 8/13
5:05 am-11:52 am
1 stop5h 47m
Norfolk
Fri 8/14
6:14 pm-12:28 am
1 stop7h 14m
$426
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Sat 6/27
1:40 pm-9:27 pm
1 stop6h 47m
Norfolk
Wed 7/1
6:48 pm-11:59 pm
1 stop6h 11m
$458
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Fri 7/10
1:50 pm-11:35 pm
2 stops8h 45m
Norfolk
Sun 7/12
8:05 pm-1:05 am
1 stop6h 00m
$472
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Wed 6/24
4:18 pm-10:30 pm
1 stop5h 12m
Norfolk
Tue 6/30
6:05 am-4:29 pm
2 stops11h 24m
$478
San AntonioNorfolk
SAT - ORF
SATORF
San Antonio
Thu 6/11
3:40 pm-11:35 pm
2 stops6h 55m
Norfolk
Mon 6/15
3:30 pm-12:05 am
1 stop9h 35m
$478
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 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 May 19, 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
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$325 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$238 | Average$471 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$238 | Average$483 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$456 | FlexibilityNo cancel fee | On-timeN/A |