$325+ Cheap flights from Jackson, MS (JAN) 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Sep 30 — Oct 71
Round-trip
1 adult, Economy
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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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Cheapest flights from Jackson to ChesapeakeExplore the most affordable flight options available from Jackson to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
Explore the most affordable flight options available from Jackson to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:08 am -
1 stop3h 48m
Wed 10/75:30 am -
1 stop4h 03m
Deal found 8/26![Delta logo]()
$325
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:30 pm -
2 stops7h 05m
Wed 10/712:05 pm -
1 stop6h 55m
Deal found 8/26![Southwest logo]()
$330
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.
Fri 9/185:55 am -
2 stops8h 15m
Tue 9/2212:40 pm -
1 stop6h 25m
Deal found 8/27![Southwest logo]()
$350
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 10/2212:00 pm -
1 stop4h 30m
Mon 10/2612:10 pm -
2 stops8h 40m
Deal found 8/27![Southwest logo]()
$363
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.
Wed 10/76:40 am -
2 stops6h 25m
Sun 10/116:20 am -
2 stops7h 00m
Deal found 8/27![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 8/30. 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 11/211:45 am -
2 stops9h 10m
Wed 11/42:10 pm -
1 stop4h 25m
Deal found 8/30![Southwest logo]()
$396
This American Airlines deal was found by Cheapflights users on 8/30. 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.
Mon 11/25:48 pm -
1 stop4h 34m
Wed 11/46:00 am -
1 stop6h 56m
Deal found 8/30![American Airlines logo]()
$404
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:05 pm -
1 stop7h 22m
Tue 9/226:10 am -
1 stop8h 13m
Deal found 8/27![United Airlines logo]()
$441
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:27 pm -
1 stop6h 14m
Mon 9/145:21 pm -
1 stop6h 31m
Deal found 8/26![American Airlines logo]()
$444
Best flights from Jackson to ChesapeakeDiscover carefully curated flight deals from Jackson to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
Discover carefully curated flight deals from Jackson to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:29 pm -
1 stop4h 16m
Mon 10/267:44 pm -
1 stop4h 25m
Deal found 8/27![Delta logo]()
$325
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 10/2212:00 pm -
2 stops8h 30m
Mon 10/2612:10 pm -
2 stops8h 40m
Deal found 8/27![Southwest logo]()
$335
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:05 pm -
1 stop7h 22m
Tue 9/226:10 am -
1 stop8h 13m
Deal found 8/27![United Airlines logo]()
$441
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:08 am -
1 stop3h 48m
Wed 10/75:30 am -
1 stop4h 03m
Deal found 8/26![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 8/30. 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 11/211:45 am -
2 stops9h 10m
Wed 11/42:10 pm -
1 stop4h 25m
Deal found 8/30![Southwest logo]()
$396
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:55 am -
2 stops8h 15m
Mon 9/141:55 pm -
1 stop5h 05m
Deal found 8/26![Southwest logo]()
$449
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:05 am -
2 stops13h 39m
Wed 11/116:15 am -
2 stops11h 19m
Deal found 8/27![United Airlines logo]()
$505
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2712:35 pm -
1 stop4h 15m
Sun 10/46:20 am -
2 stops7h 00m
Deal found 8/26![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 8/29. 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.
Sun 9/136:15 am -
2 stops7h 15m
Thu 9/171:55 pm -
1 stop5h 05m
Deal found 8/29![Southwest logo]()
$502
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated August 31, 2026 and is based on user searches.
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.
Tue 9/17:05 am -
2 stops9h 15m
Wed 9/912:40 pm -
1 stop6h 25m
Deal found 8/27![Southwest logo]()
$495
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:27 pm -
1 stop6h 14m
Mon 9/145:21 pm -
1 stop6h 31m
Deal found 8/26![American Airlines logo]()
$444
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:55 am -
2 stops8h 15m
Mon 9/141:55 pm -
1 stop5h 05m
Deal found 8/26![Southwest logo]()
$449
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.
Fri 9/185:55 am -
2 stops8h 15m
Tue 9/2212:40 pm -
1 stop6h 25m
Deal found 8/27![Southwest logo]()
$350
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:05 pm -
1 stop7h 22m
Tue 9/226:10 am -
1 stop8h 13m
Deal found 8/27![United Airlines logo]()
$441
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:08 am -
1 stop3h 48m
Wed 10/75:30 am -
1 stop4h 03m
Deal found 8/26![Delta logo]()
$325
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:30 pm -
2 stops7h 05m
Wed 10/712:05 pm -
1 stop6h 55m
Deal found 8/26![Southwest logo]()
$330
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:15 am -
2 stops8h 45m
Sun 10/412:35 pm -
2 stops8h 10m
Deal found 8/26![Southwest logo]()
$467
Find flight deals from Jackson to Chesapeake
Keep the following information in mind while searching for Jackson to Chesapeake flight deals. Data was last updated August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (Delta) |
Cheapflights Fare Finder
Customize your flight search to find flights from Jackson 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 31, 2026.
Use the filters below to find and compare flights from Jackson to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/22
7:29 pm-12:45 am
1 stop4h 16m
Norfolk
Mon 10/26
7:44 pm-11:09 pm
1 stop4h 25m
$325
Quickest round-trip
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Wed 9/23
11:08 am-3:56 pm
1 stop3h 48m
Norfolk
Wed 10/7
5:30 am-8:33 am
1 stop4h 03m
$325
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/22
12:00 pm-9:30 pm
2 stops8h 30m
Norfolk
Mon 10/26
12:10 pm-7:50 pm
2 stops8h 40m
$335
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Mon 11/2
11:45 am-9:55 pm
2 stops9h 10m
Norfolk
Wed 11/4
2:10 pm-5:35 pm
1 stop4h 25m
$396
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 9/18
2:05 pm-10:27 pm
1 stop7h 22m
Norfolk
Tue 9/22
6:10 am-1:23 pm
1 stop8h 13m
$441
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 9/10
5:55 am-3:10 pm
2 stops8h 15m
Norfolk
Mon 9/14
1:55 pm-6:00 pm
1 stop5h 05m
$449
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sun 9/27
12:35 pm-5:50 pm
1 stop4h 15m
Norfolk
Sun 10/4
6:20 am-12:20 pm
2 stops7h 00m
$488
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sun 9/13
6:15 am-2:30 pm
2 stops7h 15m
Norfolk
Thu 9/17
1:55 pm-6:00 pm
1 stop5h 05m
$502
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 11/10
9:05 am-11:44 pm
2 stops13h 39m
Norfolk
Wed 11/11
6:15 am-4:34 pm
2 stops11h 19m
$505
Sorted by cheapest first
Best time to book a flight from Jackson to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Jackson with our price prediction graph.
JAN-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 Jackson to Chesapeake
JAN-C6E
JAN-ORF
No data available for this route at this time. Please check back soon.
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 31, 2026.
Read reviews from past customers who have flown Delta from Jackson to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Overall
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Jackson 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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Alternative routes for Jackson 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.
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Jackson and Chesapeake flights
Browse other Jackson and Chesapeake flight options. Last updated on August 31, 2026.
Other flights from Jackson
Browse through other flights departing from Jackson. Flights are based on user searches made on Cheapflights and were last updated on August 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Jackson to Chesapeake flights
Consider these flights traveling from Jackson to Chesapeake.
Top 2 airlines flying from Jackson to Chesapeake
Discover the top 2 airlines that operate flights from Jackson 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 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$427 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$426 | FlexibilityNo cancel fee | On-time71% |