$381+ Cheap flights from Jackson, MS (JAN) to Chesapeake, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Jul 21 — Jul 281
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
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 21, 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 21, 2026.
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.
Fri 9/41:00 pm
JAN
- ORF
1 stop6h 21m
Delta
Mon 9/146:40 am
ORF
- JAN
1 stop6h 37m
Delta
Deal found 6/15![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/2812:20 pm
JAN
- ORF
2 stops8h 35m
Southwest
Thu 7/309:55 am
ORF
- JAN
2 stops10h 50m
Southwest
Deal found 6/16![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Mon 7/276:20 am
ORF
- JAN
1 stop6h 45m
Delta
Deal found 6/20![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 6/16. 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 10/36:15 am
JAN
- ORF
2 stops11h 55m
Southwest
Thu 10/83:55 pm
ORF
- JAN
2 stops8h 10m
Southwest
Deal found 6/16![Southwest logo]()
$424
This Southwest deal was found by Cheapflights users on 6/19. 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 7/3011:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 8/39:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/19![Southwest logo]()
$451
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:05 pm
JAN
- ORF
1 stop7h 28m
United Airlines
Wed 9/236:10 am
ORF
- JAN
1 stop6h 05m
United Airlines
Deal found 6/15![United Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 6/16. 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 7/283:06 pm
JAN
- ORF
1 stop5h 36m
Delta
Thu 7/307:59 pm
ORF
- JAN
1 stop4h 10m
Delta
Deal found 6/16![Delta logo]()
$475
This Southwest deal was found by Cheapflights users on 6/16. 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.
Fri 9/45:55 am
JAN
- ORF
2 stops11h 00m
Southwest
Sun 9/136:20 am
ORF
- JAN
2 stops12h 40m
Southwest
Deal found 6/16![Southwest logo]()
$483
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 21, 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 21, 2026.
This Delta deal was found by Cheapflights users on 6/16. 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.
Thu 9/179:14 am
JAN
- ORF
1 stop3h 40m
Delta
Sun 9/203:00 pm
ORF
- JAN
1 stop6h 37m
Delta
Deal found 6/16![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/286:00 am
JAN
- ORF
2 stops8h 00m
Southwest
Thu 7/3011:25 am
ORF
- JAN
1 stop9h 20m
Southwest
Deal found 6/16![Southwest logo]()
$401
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/307:20 am
JAN
- ORF
1 stop5h 29m
American Airlines
Mon 8/35:22 pm
ORF
- JAN
2 stops7h 26m
American Airlines
Deal found 6/19![American Airlines logo]()
$554
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Fri 9/412:00 pm
JAN
- ORF
2 stops25h 18m
United Airlines
Mon 9/147:59 pm
ORF
- JAN
2 stops18h 24m
United Airlines
Deal found 6/19![United Airlines logo]()
$695
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Mon 7/276:20 am
ORF
- JAN
1 stop6h 45m
Delta
Deal found 6/20![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 6/19. 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 7/307:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Mon 8/36:23 am
ORF
- JAN
1 stop5h 14m
Delta
Deal found 6/19![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 6/19. 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 7/3011:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 8/39:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/19![Southwest logo]()
$451
This Southwest deal was found by Cheapflights users on 6/20. 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 7/2411:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 7/279:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/20![Southwest logo]()
$527
This American Airlines deal was found by Cheapflights users on 6/18. 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 9/412:01 pm
JAN
- ORF
2 stops8h 47m
American Airlines
Mon 9/143:23 pm
ORF
- JAN
2 stops8h 29m
American Airlines
Deal found 6/18![American Airlines logo]()
$697
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated June 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 7/15:15 am
JAN
- ORF
1 stop6h 19m
American Airlines
Mon 7/68:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/18![American Airlines logo]()
$625
This Southwest deal was found by Cheapflights users on 6/18. 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.
Wed 7/16:00 am
JAN
- ORF
2 stops8h 50m
Southwest
Mon 7/66:30 am
ORF
- JAN
2 stops14h 15m
Southwest
Deal found 6/18![Southwest logo]()
$694
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Mon 7/276:20 am
ORF
- JAN
1 stop6h 45m
Delta
Deal found 6/20![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 6/20. 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 7/2411:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 7/279:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/20![Southwest logo]()
$527
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/244:24 pm
JAN
- ORF
1 stop6h 21m
American Airlines
Mon 7/276:24 pm
ORF
- JAN
1 stop6h 24m
American Airlines
Deal found 6/20![American Airlines logo]()
$579
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/2812:20 pm
JAN
- ORF
2 stops8h 35m
Southwest
Thu 7/309:55 am
ORF
- JAN
2 stops10h 50m
Southwest
Deal found 6/16![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 6/16. 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 7/283:06 pm
JAN
- ORF
1 stop5h 36m
Delta
Thu 7/307:59 pm
ORF
- JAN
1 stop4h 10m
Delta
Deal found 6/16![Delta logo]()
$475
This Southwest deal was found by Cheapflights users on 6/19. 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 7/3011:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 8/39:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/19![Southwest logo]()
$451
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/307:20 am
JAN
- ORF
1 stop5h 29m
American Airlines
Mon 8/35:22 pm
ORF
- JAN
2 stops7h 26m
American Airlines
Deal found 6/19![American Airlines logo]()
$554
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 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (Delta) |
Popular in | March |
Cheapest in | October |
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 21, 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
Thu 9/17
9:14 am-1:54 pm
1 stop3h 40m
Norfolk
Sun 9/20
3:00 pm-8:37 pm
1 stop6h 37m
$381
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 7/24
7:10 pm-12:45 am
1 stop4h 35m
Norfolk
Mon 7/27
6:20 am-12:05 pm
1 stop6h 45m
$407
Quickest round-trip
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 7/30
7:10 pm-12:45 am
1 stop4h 35m
Norfolk
Mon 8/3
6:23 am-10:37 am
1 stop5h 14m
$407
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 7/30
11:25 am-11:30 pm
2 stops11h 05m
Norfolk
Mon 8/3
9:55 am-10:00 pm
2 stops13h 05m
$451
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 7/24
11:25 am-11:30 pm
2 stops11h 05m
Norfolk
Mon 7/27
9:55 am-10:00 pm
2 stops13h 05m
$527
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 7/30
7:20 am-1:49 pm
1 stop5h 29m
Norfolk
Mon 8/3
5:22 pm-11:48 pm
2 stops7h 26m
$554
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
12:00 pm-2:18 pm
2 stops25h 18m
Norfolk
Mon 9/14
7:59 pm-1:23 pm
2 stops18h 24m
$695
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
12:01 pm-9:48 pm
2 stops8h 47m
Norfolk
Mon 9/14
3:23 pm-10:52 pm
2 stops8h 29m
$697
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 June 21, 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
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Overall
7.8
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
See prices for flight routes from nearby airports that may be better suited for you.
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 21, 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 21, 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$414 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$377 | FlexibilityNo cancel fee | On-time71% |