$163+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Sep 25 — Oct 21
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
Cheapest
Best
Last-minute
One-way
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 26, 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 26, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:04 pm -
1 stop4h 30m
Mon 10/55:02 pm -
1 stop4h 33m
Deal found 8/24![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 8/22. 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 10/305:35 am -
1 stop5h 45m
Tue 11/36:00 am -
1 stop6h 49m
Deal found 8/22![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 8/22. 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 10/3012:00 pm -
2 stops8h 45m
Tue 11/32:10 pm -
1 stop4h 25m
Deal found 8/22![Southwest logo]()
$350
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.
Wed 11/259:16 am -
1 stop5h 58m
Tue 12/17:00 am -
1 stop6h 44m
Deal found 8/23![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 8/22. 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 10/286:40 am -
2 stops6h 25m
Sat 10/316:15 am -
2 stops12h 30m
Deal found 8/22![Southwest logo]()
$368
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:25 am -
1 stop5h 49m
Sun 9/61:45 pm -
1 stop4h 48m
Deal found 8/24![American Airlines logo]()
$391
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 10/112:00 pm -
2 stops8h 25m
Mon 10/57:45 am -
2 stops13h 05m
Deal found 8/24![Southwest logo]()
$394
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.
Wed 11/255:30 am -
2 stops10h 20m
Tue 12/12:10 pm -
1 stop4h 25m
Deal found 8/24![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 8/22. 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 12/316:30 am -
2 stops6h 55m
Mon 1/49:55 am -
2 stops10h 50m
Deal found 8/22![Southwest logo]()
$421
This American Airlines deal was found by Cheapflights users on 8/22. 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 10/287:19 am -
2 stops8h 41m
Sat 10/311:36 pm -
1 stop5h 39m
Deal found 8/22![American Airlines logo]()
$432
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 26, 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 26, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 10/281:04 pm -
1 stop4h 12m
Sat 10/317:00 am -
1 stop5h 49m
Deal found 8/22![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 8/22. 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 10/3012:00 pm -
2 stops8h 45m
Tue 11/39:55 am -
2 stops8h 40m
Deal found 8/22![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/52:05 pm -
1 stop7h 28m
Wed 9/96:10 am -
1 stop6h 05m
Deal found 8/21![United Airlines logo]()
$471
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:04 pm -
1 stop4h 30m
Mon 10/55:02 pm -
1 stop4h 33m
Deal found 8/24![Delta logo]()
$325
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 10/112:00 pm -
1 stop4h 30m
Mon 10/57:45 am -
2 stops13h 05m
Deal found 8/24![Southwest logo]()
$502
This United Airlines deal was found by Cheapflights users on 8/21. 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 8/21![United Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 8/22. 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 9/187:04 pm -
1 stop4h 31m
Sun 9/205:30 am -
1 stop3h 59m
Deal found 8/22![Delta logo]()
$539
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 10/812:00 pm -
2 stops8h 25m
Sun 10/116:20 am -
2 stops7h 00m
Deal found 8/24![Southwest logo]()
$569
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated August 26, 2026 and is based on user searches.
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:32 am -
1 stop5h 07m
Tue 9/85:02 pm -
1 stop5h 32m
Deal found 8/24![Delta logo]()
$629
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:25 am -
1 stop5h 49m
Sun 9/61:45 pm -
1 stop4h 48m
Deal found 8/24![American Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/52:05 pm -
1 stop7h 28m
Wed 9/96:10 am -
1 stop6h 05m
Deal found 8/21![United Airlines logo]()
$471
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:16 am -
1 stop5h 43m
Sun 9/208:09 pm -
1 stop4h 41m
Deal found 8/23![American Airlines logo]()
$548
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:35 am -
1 stop5h 20m
Mon 9/215:02 pm -
1 stop4h 33m
Deal found 8/24![Delta logo]()
$462
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.
Fri 9/185:55 am -
2 stops8h 15m
Mon 9/211:55 pm -
1 stop5h 05m
Deal found 8/24![Southwest logo]()
$510
This Delta deal was found by Cheapflights users on 8/22. 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 9/187:04 pm -
1 stop4h 31m
Sun 9/205:30 am -
1 stop3h 59m
Deal found 8/22![Delta logo]()
$539
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/1812:14 pm -
2 stops9h 11m
Sun 9/208:09 pm -
1 stop4h 41m
Deal found 8/22![American Airlines logo]()
$604
This Southwest deal was found by Cheapflights users on 8/22. 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
Sun 9/206:20 am -
2 stops12h 45m
Deal found 8/22![Southwest logo]()
$607
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 26, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
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 10/15:14 pm -
1 stop6h 20m
Deal found 8/25![Delta logo]()
$163
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.
Thu 10/112:00 pm -
2 stops8h 25m
Deal found 8/25![Southwest logo]()
$188
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.
Thu 10/17:00 am -
3 stops15h 44m
Deal found 8/25![United Airlines logo]()
$580
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 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (American Airlines) |
One-way from | $163 (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 26, 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
Wed 10/28
1:04 pm-6:16 pm
1 stop4h 12m
Norfolk
Sat 10/31
7:00 am-11:49 am
1 stop5h 49m
$325
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/1
7:04 pm-12:34 am
1 stop4h 30m
Norfolk
Mon 10/5
5:02 pm-8:35 pm
1 stop4h 33m
$325
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 10/30
12:00 pm-9:45 pm
2 stops8h 45m
Norfolk
Tue 11/3
9:55 am-5:35 pm
2 stops8h 40m
$355
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sat 9/5
2:05 pm-10:33 pm
1 stop7h 28m
Norfolk
Wed 9/9
6:10 am-11:15 am
1 stop6h 05m
$471
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/1
12:00 pm-5:30 pm
1 stop4h 30m
Norfolk
Mon 10/5
7:45 am-7:50 pm
2 stops13h 05m
$502
Quickest round-trip
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 9/18
7:04 pm-12:35 am
1 stop4h 31m
Norfolk
Sun 9/20
5:30 am-8:29 am
1 stop3h 59m
$539
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
$545
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/8
12:00 pm-9:25 pm
2 stops8h 25m
Norfolk
Sun 10/11
6:20 am-12:20 pm
2 stops7h 00m
$569
Cheapest one-way
Quickest one-way
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/1
5:14 pm-12:34 am
1 stop6h 20m
$163
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/1
7:00 am-11:44 pm
3 stops15h 44m
$580
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 26, 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.
Overall
7.8
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
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
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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 Jackson to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jackson and Chesapeake flights
Browse other Jackson and Chesapeake flight options. Last updated on August 26, 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 26, 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 26, 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% |