$200+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Aug 18 — Aug 251
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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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 July 19, 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 July 19, 2026.
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 8/251:00 pm
JAN
- ORF
1 stop5h 02m
Delta
Wed 9/212:50 pm
ORF
- JAN
1 stop4h 26m
Delta
Deal found 7/14![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 7/16. 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 8/222:30 pm
JAN
- ORF
2 stops5h 25m
Southwest
Tue 8/2512:40 pm
ORF
- JAN
1 stop6h 25m
Southwest
Deal found 7/16![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 7/16. 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 8/2212:45 pm
JAN
- ORF
1 stop6h 35m
Delta
Tue 8/2510:20 am
ORF
- JAN
1 stop6h 56m
Delta
Deal found 7/16![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 8/277:00 pm
JAN
- ORF
1 stop5h 03m
Delta
Sun 8/307:50 am
ORF
- JAN
1 stop5h 22m
Delta
Deal found 7/15![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/222:05 pm
JAN
- ORF
1 stop7h 28m
United Airlines
Tue 8/256:10 am
ORF
- JAN
1 stop8h 13m
United Airlines
Deal found 7/16![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 7/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:49 am
JAN
- ORF
1 stop6h 41m
Delta
Mon 9/143:11 pm
ORF
- JAN
1 stop4h 08m
Delta
Deal found 7/18![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 7/17. 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.
Fri 9/1812:40 pm
JAN
- ORF
2 stops8h 15m
Southwest
Mon 9/211:55 pm
ORF
- JAN
1 stop5h 05m
Southwest
Deal found 7/17![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 7/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:35 pm
JAN
- ORF
1 stop5h 39m
Delta
Mon 11/236:05 pm
ORF
- JAN
1 stop6h 18m
Delta
Deal found 7/18![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 7/16. 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.
Tue 12/225:35 pm
JAN
- ORF
1 stop5h 39m
Delta
Mon 12/283:05 pm
ORF
- JAN
1 stop6h 01m
Delta
Deal found 7/16![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 7/14. 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 8/285:32 am
JAN
- ORF
1 stop5h 07m
Delta
Sun 8/305:23 am
ORF
- JAN
1 stop6h 14m
Delta
Deal found 7/14![Delta logo]()
$407
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 July 19, 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 July 19, 2026.
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 8/251:00 pm
JAN
- ORF
1 stop5h 02m
Delta
Wed 9/212:50 pm
ORF
- JAN
1 stop4h 26m
Delta
Deal found 7/14![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 7/14. 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.
Tue 8/257:05 am
JAN
- ORF
2 stops9h 15m
Southwest
Wed 9/212:40 pm
ORF
- JAN
1 stop6h 25m
Southwest
Deal found 7/14![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/222:05 pm
JAN
- ORF
1 stop7h 28m
United Airlines
Tue 8/256:10 am
ORF
- JAN
1 stop8h 13m
United Airlines
Deal found 7/16![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 7/16. 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 8/222:30 pm
JAN
- ORF
2 stops5h 25m
Southwest
Tue 8/258:05 am
ORF
- JAN
2 stops11h 00m
Southwest
Deal found 7/16![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 8/277:00 pm
JAN
- ORF
1 stop5h 03m
Delta
Sun 8/307:50 am
ORF
- JAN
1 stop5h 22m
Delta
Deal found 7/15![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 7/15. 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.
Fri 9/45:32 am
JAN
- ORF
1 stop6h 13m
Delta
Mon 9/146:40 am
ORF
- JAN
1 stop6h 37m
Delta
Deal found 7/15![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 7/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:35 pm
JAN
- ORF
1 stop5h 39m
Delta
Mon 11/236:05 pm
ORF
- JAN
1 stop6h 18m
Delta
Deal found 7/18![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 7/14. 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 8/285:32 am
JAN
- ORF
1 stop5h 07m
Delta
Sun 8/305:23 am
ORF
- JAN
1 stop6h 14m
Delta
Deal found 7/14![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:10 pm
JAN
- ORF
1 stop3h 49m
Delta
Sat 11/286:55 am
ORF
- JAN
1 stop4h 10m
Delta
Deal found 7/18![Delta logo]()
$407
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated July 19, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated July 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:04 pm
JAN
- ORF
1 stop6h 20m
Delta
Tue 8/410:20 am
ORF
- JAN
1 stop6h 56m
Delta
Deal found 7/18![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 7/16. 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 8/222:30 pm
JAN
- ORF
2 stops5h 25m
Southwest
Tue 8/2512:40 pm
ORF
- JAN
1 stop6h 25m
Southwest
Deal found 7/16![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 7/16. 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 8/2212:45 pm
JAN
- ORF
1 stop6h 35m
Delta
Tue 8/2510:20 am
ORF
- JAN
1 stop6h 56m
Delta
Deal found 7/16![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/222:05 pm
JAN
- ORF
1 stop7h 28m
United Airlines
Tue 8/256:10 am
ORF
- JAN
1 stop8h 13m
United Airlines
Deal found 7/16![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 8/251:00 pm
JAN
- ORF
1 stop5h 02m
Delta
Wed 9/212:50 pm
ORF
- JAN
1 stop4h 26m
Delta
Deal found 7/14![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 8/277:00 pm
JAN
- ORF
1 stop5h 03m
Delta
Sun 8/307:50 am
ORF
- JAN
1 stop5h 22m
Delta
Deal found 7/15![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Thu 8/276:35 am
JAN
- ORF
1 stop6h 27m
American Airlines
Sun 8/305:03 am
ORF
- JAN
1 stop6h 18m
American Airlines
Deal found 7/15![American Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 7/14. 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.
Thu 8/275:55 am
JAN
- ORF
2 stops11h 00m
Southwest
Sun 8/301:30 pm
ORF
- JAN
2 stops7h 45m
Southwest
Deal found 7/14![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 7/14. 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 8/285:32 am
JAN
- ORF
1 stop5h 07m
Delta
Sun 8/305:23 am
ORF
- JAN
1 stop6h 14m
Delta
Deal found 7/14![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 7/14. 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 8/285:55 am
JAN
- ORF
2 stops11h 00m
Southwest
Sun 8/301:30 pm
ORF
- JAN
2 stops7h 45m
Southwest
Deal found 7/14![Southwest logo]()
$473
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 July 19, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated July 19, 2026.
This Delta deal was found by Cheapflights users on 7/15. 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 8/1510:36 am
JAN
- ORF
1 stop3h 54m
Delta
Deal found 7/15![Delta logo]()
$200
This Southwest deal was found by Cheapflights users on 7/15. 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 8/156:00 am
JAN
- ORF
2 stops11h 15m
Southwest
Deal found 7/15![Southwest logo]()
$260
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 July 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $200 (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 2,558,603 searches. Data last updated July 19, 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
Tue 8/25
1:00 pm-7:02 pm
1 stop5h 02m
Norfolk
Wed 9/2
12:50 pm-4:16 pm
1 stop4h 26m
$317
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Tue 8/25
7:05 am-5:20 pm
2 stops9h 15m
Norfolk
Wed 9/2
12:40 pm-6:05 pm
1 stop6h 25m
$322
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 8/22
2:30 pm-8:55 pm
2 stops5h 25m
Norfolk
Tue 8/25
8:05 am-6:05 pm
2 stops11h 00m
$327
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 8/27
7:00 pm-1:03 am
1 stop5h 03m
Norfolk
Sun 8/30
7:50 am-12:12 pm
1 stop5h 22m
$362
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
5:32 am-12:45 pm
1 stop6h 13m
Norfolk
Mon 9/14
6:40 am-12:17 pm
1 stop6h 37m
$362
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 8/22
2:05 pm-10:33 pm
1 stop7h 28m
Norfolk
Tue 8/25
6:10 am-1:23 pm
1 stop8h 13m
$373
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sun 11/22
5:35 pm-12:14 am
1 stop5h 39m
Norfolk
Mon 11/23
6:05 pm-11:23 pm
1 stop6h 18m
$387
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 8/28
5:32 am-11:39 am
1 stop5h 07m
Norfolk
Sun 8/30
5:23 am-10:37 am
1 stop6h 14m
$407
Quickest round-trip
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 11/27
12:10 pm-4:59 pm
1 stop3h 49m
Norfolk
Sat 11/28
6:55 am-10:05 am
1 stop4h 10m
$407
Cheapest one-way
Quickest one-way
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 8/15
10:36 am-3:30 pm
1 stop3h 54m
$200
Showing 1-10 of 11 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
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 July 19, 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.
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.8
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
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Jackson and Chesapeake flights
Browse other Jackson and Chesapeake flight options. Last updated on July 19, 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 July 19, 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 2,558,603 searches. Data last updated July 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$419 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$377 | FlexibilityNo cancel fee | On-time71% |