$196+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Jul 16 — Jul 231
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 June 16, 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 June 16, 2026.
This American Airlines deal was found by Cheapflights users on 6/11. 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 10/246:45 pm
JAN
- ORF
1 stop3h 54m
American Airlines
Tue 10/278:21 pm
ORF
- JAN
1 stop4h 48m
American Airlines
Deal found 6/11![American Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 6/11. 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 10/246:15 am
JAN
- ORF
2 stops8h 05m
Southwest
Tue 10/276:05 am
ORF
- JAN
2 stops7h 25m
Southwest
Deal found 6/11![Southwest logo]()
$284
This Delta deal was found by Cheapflights users on 6/15. 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 9/235:03 pm
JAN
- ORF
1 stop4h 08m
Delta
Wed 9/308:00 am
ORF
- JAN
1 stop5h 17m
Delta
Deal found 6/15![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 6/15. 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 9/237:05 am
JAN
- ORF
2 stops9h 15m
Southwest
Wed 9/3012:40 pm
ORF
- JAN
1 stop6h 25m
Southwest
Deal found 6/15![Southwest logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/254:24 pm
JAN
- ORF
1 stop6h 54m
American Airlines
Tue 7/288:16 pm
ORF
- JAN
1 stop4h 32m
American Airlines
Deal found 6/15![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/11. 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 9/177:51 am
JAN
- ORF
1 stop5h 03m
Delta
Sun 9/206:40 am
ORF
- JAN
1 stop6h 37m
Delta
Deal found 6/11![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 6/11. 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
JAN
- ORF
1 stop6h 21m
Delta
Mon 9/146:40 am
ORF
- JAN
1 stop6h 37m
Delta
Deal found 6/11![Delta logo]()
$377
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/225:00 am
JAN
- ORF
1 stop6h 34m
American Airlines
Sun 7/268:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/14![American Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2512:20 pm
JAN
- ORF
2 stops8h 15m
Southwest
Tue 7/2810:05 am
ORF
- JAN
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 6/15. 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 7/255:04 pm
JAN
- ORF
1 stop6h 20m
Delta
Mon 7/276:17 pm
ORF
- JAN
1 stop5h 52m
Delta
Deal found 6/15![Delta logo]()
$394
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 June 16, 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 June 16, 2026.
This Delta deal was found by Cheapflights users on 6/11. 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
JAN
- ORF
1 stop6h 21m
Delta
Mon 9/146:40 am
ORF
- JAN
1 stop6h 37m
Delta
Deal found 6/11![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2512:20 pm
JAN
- ORF
2 stops8h 15m
Southwest
Tue 7/2810:05 am
ORF
- JAN
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$391
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/254:24 pm
JAN
- ORF
1 stop6h 54m
American Airlines
Sun 7/268:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/15![American Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/252:05 pm
JAN
- ORF
1 stop7h 28m
United Airlines
Wed 8/266:15 am
ORF
- JAN
2 stops8h 08m
United Airlines
Deal found 6/11![United Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 6/15. 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 7/286:00 am
JAN
- ORF
2 stops8h 00m
Southwest
Thu 7/3011:25 am
ORF
- JAN
1 stop9h 20m
Southwest
Deal found 6/15![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 6/14. 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
JAN
- ORF
1 stop6h 21m
Delta
Sun 9/137:00 am
ORF
- JAN
1 stop3h 59m
Delta
Deal found 6/14![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 6/11. 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
JAN
- ORF
1 stop6h 21m
Delta
Mon 9/75:23 am
ORF
- JAN
1 stop5h 20m
Delta
Deal found 6/11![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2512:20 pm
JAN
- ORF
1 stop7h 20m
Southwest
Mon 7/279:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/15![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 6/11. 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 6/187:00 pm
JAN
- ORF
1 stop4h 45m
Delta
Sat 6/208:26 am
ORF
- JAN
1 stop5h 00m
Delta
Deal found 6/11![Delta logo]()
$625
This Southwest deal was found by Cheapflights users on 6/11. 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 7/311:25 am
JAN
- ORF
2 stops9h 35m
Southwest
Sun 7/53:15 pm
ORF
- JAN
2 stops7h 50m
Southwest
Deal found 6/11![Southwest logo]()
$670
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated June 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/225:00 am
JAN
- ORF
1 stop6h 34m
American Airlines
Sun 7/268:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/14![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/254:24 pm
JAN
- ORF
1 stop6h 54m
American Airlines
Tue 7/288:16 pm
ORF
- JAN
1 stop4h 32m
American Airlines
Deal found 6/15![American Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2512:20 pm
JAN
- ORF
2 stops8h 15m
Southwest
Tue 7/2810:05 am
ORF
- JAN
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 6/15. 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 7/255:04 pm
JAN
- ORF
1 stop6h 20m
Delta
Mon 7/276:17 pm
ORF
- JAN
1 stop5h 52m
Delta
Deal found 6/15![Delta logo]()
$394
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/254:24 pm
JAN
- ORF
1 stop6h 54m
American Airlines
Sun 7/268:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/15![American Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2512:20 pm
JAN
- ORF
2 stops8h 15m
Southwest
Mon 7/279:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/15![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2812:20 pm
JAN
- ORF
2 stops8h 35m
Southwest
Thu 7/309:55 am
ORF
- JAN
2 stops10h 50m
Southwest
Deal found 6/15![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 6/15. 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.
Tue 7/283:06 pm
JAN
- ORF
1 stop5h 36m
Delta
Thu 7/307:59 pm
ORF
- JAN
1 stop4h 10m
Delta
Deal found 6/15![Delta logo]()
$475
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 June 16, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/15. 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 7/255:35 am
JAN
- ORF
2 stops8h 40m
Southwest
Deal found 6/15![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 6/14. 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
JAN
- ORF
1 stop6h 21m
Delta
Deal found 6/14![Delta logo]()
$248
This Southwest deal was found by Cheapflights users on 6/14. 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 9/45:55 am
JAN
- ORF
2 stops11h 00m
Southwest
Deal found 6/14![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 6/14. 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 9/35:32 am
JAN
- ORF
1 stop5h 07m
Delta
Deal found 6/14![Delta logo]()
$320
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (American Airlines) |
One-way from | $196 (Southwest) |
Popular in | March |
Cheapest in | August |
Average price | $640 |
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 June 16, 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 - ORF
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
$377
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 7/25
12:20 pm-9:35 pm
2 stops8h 15m
Norfolk
Tue 7/28
10:05 am-6:45 pm
2 stops9h 40m
$391
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Tue 7/28
6:00 am-3:00 pm
2 stops8h 00m
Norfolk
Thu 7/30
11:25 am-7:45 pm
1 stop9h 20m
$401
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
1:00 pm-8:21 pm
1 stop6h 21m
Norfolk
Sun 9/13
7:00 am-9:59 am
1 stop3h 59m
$407
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 7/25
4:24 pm-12:18 am
1 stop6h 54m
Norfolk
Sun 7/26
8:20 pm-11:48 pm
1 stop4h 28m
$419
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
1:00 pm-8:21 pm
1 stop6h 21m
Norfolk
Mon 9/7
5:23 am-9:43 am
1 stop5h 20m
$432
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 7/25
12:20 pm-8:40 pm
1 stop7h 20m
Norfolk
Mon 7/27
9:55 am-10:00 pm
2 stops13h 05m
$443
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Tue 8/25
2:05 pm-10:33 pm
1 stop7h 28m
Norfolk
Wed 8/26
6:15 am-1:23 pm
2 stops8h 08m
$506
Quickest round-trip
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 6/18
7:00 pm-12:45 am
1 stop4h 45m
Norfolk
Sat 6/20
8:26 am-12:26 pm
1 stop5h 00m
$625
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 7/3
11:25 am-10:00 pm
2 stops9h 35m
Norfolk
Sun 7/5
3:15 pm-10:05 pm
2 stops7h 50m
$670
Showing 1-10 of 14 resultsSorted 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
How much does it cost to fly round-trip from Jackson, Mississippi to Chesapeake?
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 June 16, 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.
Entertainment
7.8
Overall
7.9
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
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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Jackson and Chesapeake flights
Browse other Jackson and Chesapeake flight options. Last updated on June 16, 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 June 16, 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$426 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$377 | FlexibilityNo cancel fee | On-time71% |