$341+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Sep 7 — Sep 141
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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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 8, 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 8, 2026.
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:36 am -
1 stop5h 32m
Wed 9/910:52 am -
1 stop4h 25m
Deal found 8/7![Delta logo]()
$365
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/113:27 pm -
1 stop4h 21m
Sun 9/138:09 pm -
1 stop4h 41m
Deal found 8/4![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/4. 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 12/195:35 pm -
1 stop5h 39m
Tue 12/296:55 am -
1 stop5h 27m
Deal found 8/4![Delta logo]()
$378
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:01 pm -
1 stop7h 02m
Tue 9/85:02 pm -
1 stop3h 47m
Deal found 8/7![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 8/6. 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 9/312:40 pm -
2 stops8h 00m
Tue 9/812:15 pm -
2 stops8h 35m
Deal found 8/6![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 8/3. 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 10/1512:00 pm -
2 stops8h 45m
Sun 10/186:20 am -
2 stops7h 00m
Deal found 8/3![Southwest logo]()
$414
This Delta deal was found by Cheapflights users on 8/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:04 pm -
1 stop4h 31m
Sun 9/205:30 am -
1 stop3h 59m
Deal found 8/8![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:49 am -
1 stop3h 56m
Wed 9/95:02 pm -
1 stop3h 47m
Deal found 8/7![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 8/4. 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 8/4![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 8/5. 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 10/45:45 am -
2 stops12h 05m
Sun 10/116:20 am -
2 stops7h 00m
Deal found 8/5![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 8/7. 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 9/412:40 pm -
2 stops8h 00m
Fri 9/1110:10 am -
2 stops11h 05m
Deal found 8/7![Southwest logo]()
$438
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 8, 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 8, 2026.
This Delta deal was found by Cheapflights users on 8/3. 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 10/153:33 pm -
1 stop3h 52m
Sun 10/185:30 am -
1 stop4h 03m
Deal found 8/3![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 8/6. 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 9/312:40 pm -
2 stops8h 00m
Tue 9/812:15 pm -
2 stops8h 35m
Deal found 8/6![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:49 am -
1 stop3h 56m
Wed 9/95:02 pm -
1 stop3h 47m
Deal found 8/7![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 8/7. 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 9/412:40 pm -
2 stops8h 00m
Fri 9/1110:10 am -
2 stops11h 05m
Deal found 8/7![Southwest logo]()
$438
This Southwest deal was found by Cheapflights users on 8/4. 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 12/195:10 am -
2 stops10h 55m
Tue 12/291:30 pm -
2 stops9h 45m
Deal found 8/4![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:01 pm -
1 stop7h 02m
Tue 8/256:23 am -
1 stop5h 14m
Deal found 8/6![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 8/7. 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 9/412:40 pm -
2 stops8h 20m
Mon 10/57:45 am -
2 stops13h 05m
Deal found 8/7![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 8/3. 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 10/1512:00 pm -
1 stop4h 30m
Sun 10/186:20 am -
2 stops7h 00m
Deal found 8/3![Southwest logo]()
$473
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated August 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:36 am -
1 stop5h 32m
Wed 9/910:52 am -
1 stop4h 25m
Deal found 8/7![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:01 pm -
1 stop7h 02m
Tue 9/85:02 pm -
1 stop3h 47m
Deal found 8/7![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 8/6. 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 9/312:40 pm -
2 stops8h 00m
Tue 9/812:15 pm -
2 stops8h 35m
Deal found 8/6![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:49 am -
1 stop3h 56m
Wed 9/95:02 pm -
1 stop3h 47m
Deal found 8/7![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:49 am -
1 stop3h 56m
Tue 9/85:02 pm -
1 stop3h 47m
Deal found 8/7![Delta logo]()
$458
This Southwest deal was found by Cheapflights users on 8/4. 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 8/4![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 8/7. 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 9/412:40 pm -
2 stops8h 00m
Fri 9/1110:10 am -
2 stops11h 05m
Deal found 8/7![Southwest logo]()
$438
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/113:27 pm -
1 stop4h 21m
Sun 9/138:09 pm -
1 stop4h 41m
Deal found 8/4![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:04 pm -
1 stop4h 31m
Sun 9/205:30 am -
1 stop3h 59m
Deal found 8/8![Delta logo]()
$417
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 8, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This United Airlines deal was found by Cheapflights users on 8/4. 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 8/142:05 pm -
1 stop7h 28m
Deal found 8/4![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 8/4. 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 8/145:55 am -
2 stops11h 00m
Deal found 8/4![Southwest logo]()
$346
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 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $365 (Delta) |
One-way from | $341 (United Airlines) |
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 2,558,603 searches. Data last updated August 8, 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 10/15
3:33 pm-8:25 pm
1 stop3h 52m
Norfolk
Sun 10/18
5:30 am-8:33 am
1 stop4h 03m
$391
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 9/3
12:40 pm-9:40 pm
2 stops8h 00m
Norfolk
Tue 9/8
12:15 pm-7:50 pm
2 stops8h 35m
$401
Quickest round-trip
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 9/3
7:49 am-12:45 pm
1 stop3h 56m
Norfolk
Wed 9/9
5:02 pm-7:49 pm
1 stop3h 47m
$432
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 9/4
12:40 pm-9:40 pm
2 stops8h 00m
Norfolk
Fri 9/11
10:10 am-8:15 pm
2 stops11h 05m
$438
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sat 12/19
5:10 am-5:05 pm
2 stops10h 55m
Norfolk
Tue 12/29
1:30 pm-10:15 pm
2 stops9h 45m
$444
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 9/4
12:40 pm-10:00 pm
2 stops8h 20m
Norfolk
Mon 10/5
7:45 am-7:50 pm
2 stops13h 05m
$458
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Thu 10/15
12:00 pm-5:30 pm
1 stop4h 30m
Norfolk
Sun 10/18
6:20 am-12:20 pm
2 stops7h 00m
$473
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 8/21
5:01 pm-1:03 am
1 stop7h 02m
Norfolk
Tue 8/25
6:23 am-10:37 am
1 stop5h 14m
$497
Cheapest one-way
Quickest one-way
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 8/14
2:05 pm-10:33 pm
1 stop7h 28m
$341
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 8/14
5:55 am-5:55 pm
2 stops11h 00m
$346
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 8, 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
Comfort
7.8
Overall
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Comfort
7.8
Overall
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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 8, 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 8, 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 2,558,603 searches. Data last updated August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$377 | FlexibilityNo cancel fee | On-time71% |