$249+ Cheap flights from Jackson, MS (JAN) 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Sep 19 — Sep 261
Round-trip
1 adult, Economy
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Find cheap flights from Jackson 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 Jackson to Chesapeake
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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 20, 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 20, 2026.
This Delta deal was found by Cheapflights users on 8/19. 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 10/13:02 pm -
1 stop6h 21m
Mon 10/55:30 am -
1 stop3h 59m
Deal found 8/19![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 8/19. 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 10/112:00 pm -
2 stops8h 45m
Mon 10/57:45 am -
2 stops13h 05m
Deal found 8/19![Southwest logo]()
$394
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:40 pm -
2 stops8h 00m
Mon 9/211:55 pm -
1 stop5h 05m
Deal found 8/18![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:40 pm -
2 stops8h 20m
Mon 9/2810:10 am -
2 stops11h 05m
Deal found 8/18![Southwest logo]()
$478
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/183:27 pm -
1 stop6h 14m
Mon 9/215:21 pm -
1 stop6h 31m
Deal found 8/18![American Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/112:14 pm -
2 stops8h 47m
Mon 10/57:59 pm -
1 stop4h 56m
Deal found 8/19![American Airlines logo]()
$518
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/65:46 pm -
1 stop3h 59m
Fri 10/91:37 pm -
1 stop5h 38m
Deal found 8/19![American Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:36 am -
1 stop3h 54m
Tue 9/16:23 am -
1 stop6h 49m
Deal found 8/17![Delta logo]()
$543
This Southwest deal was found by Cheapflights users on 8/20. 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 9/412:40 pm -
2 stops8h 20m
Sun 9/67:10 am -
1 stop10h 35m
Deal found 8/20![Southwest logo]()
$544
This Southwest deal was found by Cheapflights users on 8/17. 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.
Sat 8/296:00 am -
2 stops11h 15m
Tue 9/112:40 pm -
1 stop6h 25m
Deal found 8/17![Southwest logo]()
$548
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 20, 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 20, 2026.
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:40 pm -
2 stops8h 20m
Mon 9/2810:10 am -
2 stops11h 05m
Deal found 8/18![Southwest logo]()
$478
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/65:46 pm -
1 stop3h 59m
Fri 10/91:37 pm -
1 stop5h 38m
Deal found 8/19![American Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:00 pm -
1 stop6h 21m
Mon 9/146:40 am -
1 stop6h 37m
Deal found 8/16![Delta logo]()
$562
This United Airlines deal was found by Cheapflights users on 8/19. 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 1/51:57 pm -
2 stops23h 19m
Thu 1/76:00 am -
1 stop6h 13m
Deal found 8/19![United Airlines logo]()
$606
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated August 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:55 am -
2 stops11h 00m
Thu 9/31:55 pm -
1 stop5h 05m
Deal found 8/18![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:36 am -
1 stop3h 54m
Tue 9/16:23 am -
1 stop6h 49m
Deal found 8/17![Delta logo]()
$543
This Southwest deal was found by Cheapflights users on 8/17. 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.
Sat 8/296:00 am -
2 stops11h 15m
Tue 9/112:40 pm -
1 stop6h 25m
Deal found 8/17![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 8/20. 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 9/412:40 pm -
2 stops8h 20m
Sun 9/67:10 am -
1 stop10h 35m
Deal found 8/20![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:00 pm -
1 stop6h 21m
Mon 9/146:40 am -
1 stop6h 37m
Deal found 8/16![Delta logo]()
$562
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:40 pm -
2 stops8h 00m
Mon 9/211:55 pm -
1 stop5h 05m
Deal found 8/18![Southwest logo]()
$467
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/183:27 pm -
1 stop6h 14m
Mon 9/215:21 pm -
1 stop6h 31m
Deal found 8/18![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:40 pm -
2 stops8h 20m
Mon 9/2810:10 am -
2 stops11h 05m
Deal found 8/18![Southwest logo]()
$478
One-way flights from Jackson to ChesapeakeSearch for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:01 pm -
1 stop6h 35m
Deal found 8/16![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 8/16. 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.
Sat 8/292:30 pm -
2 stops5h 25m
Deal found 8/16![Southwest logo]()
$254
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 8/299:20 am -
3 stops23h 14m
Deal found 8/16![United Airlines logo]()
$562
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 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (Delta) |
One-way from | $249 (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 20, 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 9/24
12:40 pm-10:00 pm
2 stops8h 20m
Norfolk
Mon 9/28
10:10 am-8:15 pm
2 stops11h 05m
$478
Quickest round-trip
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 10/6
5:46 pm-10:45 pm
1 stop3h 59m
Norfolk
Fri 10/9
1:37 pm-6:15 pm
1 stop5h 38m
$520
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 9/4
1:00 pm-8:21 pm
1 stop6h 21m
Norfolk
Mon 9/14
6:40 am-12:17 pm
1 stop6h 37m
$562
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 1/5
1:57 pm-2:16 pm
2 stops23h 19m
Norfolk
Thu 1/7
6:00 am-11:13 am
1 stop6h 13m
$606
Cheapest one-way
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sat 8/29
5:01 pm-12:36 am
1 stop6h 35m
$249
Quickest one-way
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sat 8/29
2:30 pm-8:55 pm
2 stops5h 25m
$254
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sat 8/29
9:20 am-9:34 am
3 stops23h 14m
$562
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 20, 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.
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
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
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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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Jackson and Chesapeake flights
Browse other Jackson and Chesapeake flight options. Last updated on August 20, 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 20, 2026.
Popular flight searches
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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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$427 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$377 | FlexibilityNo cancel fee | On-time71% |