$128+ Cheap flights from San Antonio (SAT) to Chesapeake, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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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 September 11, 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 September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:05 am -
1 stop26h 08m
Tue 10/131:19 pm -
2 stops20h 49m
Deal found 9/11![Multiple Airlines logo]()
$257
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:05 am -
1 stop7h 43m
Tue 10/137:41 pm -
1 stop14h 27m
Deal found 9/11![Frontier logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/710:03 am -
1 stop7h 45m
Sun 10/117:41 pm -
1 stop14h 27m
Deal found 9/9![Frontier logo]()
$317
This CheapOair deal was found by Cheapflights users on 9/9. 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 10/210:05 am -
1 stop7h 43m
Sun 10/117:41 pm -
1 stop14h 27m
Deal found 9/9![Frontier logo]()
$338
This CheapOair deal was found by Cheapflights users on 9/6. 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 10/210:05 am -
1 stop7h 43m
Sun 10/47:43 pm -
1 stop14h 27m
Deal found 9/6![Frontier logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/8. 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 9/297:28 am -
1 stop9h 19m
Mon 10/57:07 pm -
1 stop5h 52m
Deal found 9/8![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/292:25 pm -
2 stops8h 19m
Mon 10/55:01 pm -
1 stop6h 49m
Deal found 9/8![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 9/10. 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 10/147:20 am -
2 stops11h 35m
Mon 10/195:50 pm -
1 stop7h 55m
Deal found 9/10![Southwest logo]()
$366
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 September 11, 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 September 11, 2026.
This Southwest deal was found by Cheapflights users on 9/8. 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 9/296:50 am -
2 stops8h 05m
Mon 10/512:10 pm -
2 stops6h 55m
Deal found 9/8![Southwest logo]()
$404
This United Airlines deal was found by Cheapflights users on 9/7. 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 2/97:00 am -
1 stop8h 45m
Wed 2/104:56 pm -
1 stop7h 03m
Deal found 9/7![United Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 9/7. 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 10/301:10 pm -
2 stops7h 20m
Mon 11/25:55 pm -
2 stops7h 10m
Deal found 9/7![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 9/6. 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 12/36:45 am -
2 stops6h 40m
Mon 12/72:10 pm -
2 stops8h 30m
Deal found 9/6![Southwest logo]()
$441
This Southwest deal was found by Cheapflights users on 9/10. 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 10/163:20 pm -
2 stops7h 20m
Mon 10/195:50 pm -
1 stop7h 55m
Deal found 9/10![Southwest logo]()
$441
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated September 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/8. 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 9/297:28 am -
1 stop9h 19m
Mon 10/57:07 pm -
1 stop5h 52m
Deal found 9/8![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/292:25 pm -
2 stops8h 19m
Mon 10/55:01 pm -
1 stop6h 49m
Deal found 9/8![United Airlines logo]()
$360
This CheapOair deal was found by Cheapflights users on 9/9. 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 10/210:05 am -
1 stop7h 43m
Sun 10/117:41 pm -
1 stop14h 27m
Deal found 9/9![Frontier logo]()
$338
This CheapOair deal was found by Cheapflights users on 9/6. 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 10/210:05 am -
1 stop7h 43m
Sun 10/47:43 pm -
1 stop14h 27m
Deal found 9/6![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:05 am -
1 stop26h 08m
Tue 10/131:19 pm -
2 stops20h 49m
Deal found 9/11![Multiple Airlines logo]()
$257
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:05 am -
1 stop7h 43m
Tue 10/137:41 pm -
1 stop14h 27m
Deal found 9/11![Frontier logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/710:03 am -
1 stop7h 45m
Sun 10/117:41 pm -
1 stop14h 27m
Deal found 9/9![Frontier logo]()
$317
This Southwest deal was found by Cheapflights users on 9/10. 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 10/147:20 am -
2 stops11h 35m
Mon 10/195:50 pm -
1 stop7h 55m
Deal found 9/10![Southwest logo]()
$366
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 September 11, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Priceline deal was found by Cheapflights users on 9/8. 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.
Wed 10/2110:03 am -
1 stop7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$128
This Priceline deal was found by Cheapflights users on 9/9. 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 -
1 stop7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$143
This Priceline deal was found by Cheapflights users on 9/7. 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 10/510:05 am -
1 stop7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$149
This Frontier deal was found by Cheapflights users on 9/6. 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.
Wed 10/710:03 am -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/49:25 am -
2 stops50h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$173
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/38:55 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/32:47 pm -
2 stops20h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/68:20 pm -
2 stops39h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$183
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Kiwi.com) |
One-way from | $128 (Priceline) |
Popular in | February |
Cheapest in | March |
Average price | $465 |
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 7,457,451 searches. Data last updated September 11, 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 San Antonio - ORF Norfolk
SATORF
San Antonio
Sun 10/4
9:25 am-12:29 pm
2 stops50h 04m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 10/22
6:35 am-3:16 pm
1 stop7h 41m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 10/21
12:30 pm-10:10 pm
2 stops8h 40m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Sun 10/4
8:20 pm-12:29 pm
2 stops39h 09m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 9/16
10:03 am-6:48 pm
1 stop7h 45m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
Quickest round-trip
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Tue 10/6
6:20 pm-12:45 am
1 stop5h 25m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$216
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Sun 10/4
2:58 pm-12:10 am
1 stop8h 12m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$249
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 10/7
9:48 am-11:44 pm
3 stops12h 56m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$271
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Fri 9/25
1:20 pm-10:41 pm
1 stop8h 21m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Sat 9/19
8:20 pm-12:18 am
3 stops50h 58m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$354
Showing 1-10 of 15 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 below average for this route at the moment.
San Antonio to Chesapeake flights typically cost between $385 and $547 in October.The cheapest round-trip price found within the last 5 days was $257 on Multiple Airlines (Oct 5-Oct 13).
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 September 11, 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.
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
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.
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Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
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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 September 11, 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 September 11, 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$286 | Average$460 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$329 | Average$506 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$365 | Average$466 | FlexibilityNo cancel fee | On-time63% |