$128+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — RIC
Sep 27 — Oct 41
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
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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
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Best
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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 August 28, 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 August 28, 2026.
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:03 am -
1 stop7h 45m
Thu 10/157:41 pm -
1 stop14h 27m
Deal found 8/24![Frontier logo]()
$281
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:05 am -
1 stop7h 43m
Tue 9/297:43 pm -
1 stop14h 24m
Deal found 8/25![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Thu 10/19:25 am -
2 stops52h 26m
Tue 10/67:43 pm -
1 stop14h 24m
Deal found 8/27![Multiple Airlines logo]()
$327
This CheapOair deal was found by Cheapflights users on 8/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:05 am -
1 stop7h 43m
Sun 9/137:43 pm -
1 stop14h 27m
Deal found 8/26![Frontier logo]()
$340
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:30 am -
1 stop7h 47m
Fri 9/116:02 am -
1 stop6h 49m
Deal found 8/24![United Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Sun 9/64:08 pm -
1 stop5h 25m
Thu 9/103:00 pm -
2 stops8h 44m
Deal found 8/25![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 8/25. 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.
Fri 9/112:05 pm -
2 stops6h 35m
Tue 9/293:20 pm -
2 stops8h 50m
Deal found 8/25![Southwest logo]()
$366
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:05 am -
1 stop7h 43m
Sun 9/207:43 pm -
1 stop14h 27m
Deal found 8/24![Frontier logo]()
$368
This American Airlines deal was found by Cheapflights users on 8/28. 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 11/66:00 am -
1 stop8h 07m
Tue 11/105:59 pm -
1 stop6h 56m
Deal found 8/28![American Airlines logo]()
$370
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 August 28, 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 August 28, 2026.
This Delta deal was found by Cheapflights users on 8/23. 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 12/46:16 am -
1 stop6h 38m
Mon 12/74:56 pm -
1 stop7h 02m
Deal found 8/23![Delta logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Thu 11/52:20 pm -
2 stops8h 24m
Sun 11/86:15 am -
1 stop5h 58m
Deal found 8/26![United Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 8/27. 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 10/112:20 pm -
2 stops8h 05m
Tue 10/69:55 am -
2 stops9h 05m
Deal found 8/27![Southwest logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Wed 10/710:03 am -
1 stop7h 45m
Mon 10/126:00 am -
2 stops38h 26m
Deal found 8/24![Multiple Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 8/27. 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.
Sat 9/196:00 am -
1 stop8h 00m
Sun 10/47:00 am -
2 stops14h 50m
Deal found 8/27![Southwest logo]()
$417
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Tue 2/92:15 pm -
1 stop7h 00m
Wed 2/105:15 pm -
1 stop6h 43m
Deal found 8/26![United Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 11/195:30 am -
1 stop7h 00m
Sun 11/226:15 am -
2 stops7h 40m
Deal found 8/24![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 11/52:50 pm -
2 stops7h 40m
Sun 11/86:15 am -
2 stops7h 40m
Deal found 8/24![Southwest logo]()
$431
Last-minute flights from San Antonio to ChesapeakeDiscover last-minute flight deals from San Antonio to Chesapeake. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chesapeake. Data last updated August 28, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:30 am -
1 stop7h 47m
Fri 9/116:02 am -
1 stop6h 49m
Deal found 8/24![United Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Tue 9/810:24 pm -
2 stops37h 05m
Tue 9/297:43 pm -
1 stop14h 24m
Deal found 8/25![Frontier logo]()
$426
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:05 am -
1 stop7h 43m
Tue 9/297:43 pm -
1 stop14h 24m
Deal found 8/25![Frontier logo]()
$323
This CheapOair deal was found by Cheapflights users on 8/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:05 am -
1 stop7h 43m
Sun 9/137:43 pm -
1 stop14h 27m
Deal found 8/26![Frontier logo]()
$340
This Southwest deal was found by Cheapflights users on 8/25. 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.
Fri 9/112:05 pm -
2 stops6h 35m
Tue 9/293:20 pm -
2 stops8h 50m
Deal found 8/25![Southwest logo]()
$366
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:05 am -
1 stop7h 43m
Sun 9/207:43 pm -
1 stop14h 27m
Deal found 8/24![Frontier logo]()
$368
This American Airlines deal was found by Cheapflights users on 8/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/194:27 pm -
1 stop6h 46m
Sun 10/46:15 pm -
1 stop5h 09m
Deal found 8/27![American Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 8/27. 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.
Sat 9/196:00 am -
1 stop8h 00m
Sun 10/47:00 am -
2 stops14h 50m
Deal found 8/27![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 8/25. 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.
Tue 9/296:50 am -
2 stops8h 05m
Sun 10/47:45 pm -
1 stop6h 15m
Deal found 8/25![Southwest logo]()
$411
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 August 28, 2026.
Search for one-way flight options from San Antonio to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Priceline deal was found by Cheapflights users on 8/26. 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.
Wed 10/2110:03 am -
1 stop7h 43m
Deal found 8/26![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Wed 10/1410:03 am -
2 stops25h 31m
Deal found 8/25![Frontier logo]()
$142
This Priceline deal was found by Cheapflights users on 8/24. 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 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
Deal found 8/24![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Tue 10/68:20 pm -
2 stops39h 24m
Deal found 8/26![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Sat 9/262:47 pm -
2 stops20h 42m
Deal found 8/27![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Tue 9/228:20 pm -
2 stops39h 09m
Deal found 8/27![Frontier logo]()
$169
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:20 pm -
1 stop5h 25m
Deal found 8/25![Delta logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Tue 9/158:20 pm -
2 stops39h 09m
Deal found 8/24![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Thu 10/158:21 pm -
2 stops41h 34m
Deal found 8/26![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Thu 10/2210:34 pm -
2 stops39h 21m
Deal found 8/26![Frontier logo]()
$181
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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (CheapOair) |
One-way from | $128 (Priceline) |
Popular in | January |
Cheapest in | February |
Average price | $420 |
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 August 28, 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 San Antonio - ORF Norfolk
SATORF
San Antonio
Fri 12/4
6:16 am-1:54 pm
1 stop6h 38m
Norfolk
Mon 12/7
4:56 pm-10:58 pm
1 stop7h 02m
$370
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 11/5
2:20 pm-11:44 pm
2 stops8h 24m
Norfolk
Sun 11/8
6:15 am-11:13 am
1 stop5h 58m
$411
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 10/1
12:20 pm-9:25 pm
2 stops8h 05m
Norfolk
Tue 10/6
9:55 am-6:00 pm
2 stops9h 05m
$413
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Sat 9/19
6:00 am-3:00 pm
1 stop8h 00m
Norfolk
Sun 10/4
7:00 am-8:50 pm
2 stops14h 50m
$417
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 11/19
5:30 am-1:30 pm
1 stop7h 00m
Norfolk
Sun 11/22
6:15 am-12:55 pm
2 stops7h 40m
$426
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Thu 11/5
2:50 pm-11:30 pm
2 stops7h 40m
Norfolk
Sun 11/8
6:15 am-12:55 pm
2 stops7h 40m
$431
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 10/7
10:03 am-6:48 pm
1 stop7h 45m
Norfolk
Mon 10/12
6:00 am-7:26 pm
2 stops38h 26m
$442
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Tue 2/9
2:15 pm-10:15 pm
1 stop7h 00m
Norfolk
Wed 2/10
5:15 pm-10:58 pm
1 stop6h 43m
$445
Cheapest one-way
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Wed 10/21
10:03 am-6:46 pm
1 stop7h 43m
$128
Quickest one-way
San AntonioNorfolk
SAT San Antonio - ORF Norfolk
SATORF
San Antonio
Tue 9/15
1:55 pm-8:13 pm
1 stop5h 18m
$178
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?
Airfare is below average for this route at the moment.
San Antonio to Chesapeake flights typically cost between $410 and $600 in October.The cheapest round-trip price found within the last 5 days was $281 on Frontier (Oct 7-Oct 15).
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 August 28, 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
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
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
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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 August 28, 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 August 28, 2026.
Popular flight searches
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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 August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$286 | Average$460 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$329 | Average$497 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$365 | Average$466 | FlexibilityNo cancel fee | On-time63% |