$244+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Jun 30 — Jul 71
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
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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 May 31, 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 May 31, 2026.
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 7/74:24 pm
JAN
- ORF
1 stop6h 17m
American Airlines
Sat 7/118:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 5/29![American Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 5/27. 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 9/176:55 pm
JAN
- ORF
1 stop4h 38m
Delta
Sun 9/206:40 am
ORF
- JAN
1 stop6h 37m
Delta
Deal found 5/27![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 5/26. 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
Mon 8/311:55 pm
ORF
- JAN
1 stop5h 05m
Southwest
Deal found 5/26![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 5/29. 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 7/97:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Sat 7/116:00 am
ORF
- JAN
1 stop4h 33m
Delta
Deal found 5/29![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 5/29. 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 9/175:55 am
JAN
- ORF
2 stops11h 00m
Southwest
Sun 9/206:20 am
ORF
- JAN
2 stops12h 40m
Southwest
Deal found 5/29![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 5/30. 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.
Mon 6/2911:25 am
JAN
- ORF
2 stops11h 00m
Southwest
Sat 7/47:10 am
ORF
- JAN
2 stops9h 05m
Southwest
Deal found 5/30![Southwest logo]()
$423
This Southwest deal was found by Cheapflights users on 5/29. 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 7/812:20 pm
JAN
- ORF
2 stops8h 35m
Southwest
Sat 7/117:30 am
ORF
- JAN
2 stops12h 05m
Southwest
Deal found 5/29![Southwest logo]()
$451
This Delta deal was found by Cheapflights users on 5/27. 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 15m
Delta
Mon 9/145:30 am
ORF
- JAN
1 stop6h 03m
Delta
Deal found 5/27![Delta logo]()
$455
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 May 31, 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 May 31, 2026.
This Delta deal was found by Cheapflights users on 5/26. 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 9/173:03 pm
JAN
- ORF
1 stop6h 08m
Delta
Sun 9/205:02 pm
ORF
- JAN
1 stop7h 06m
Delta
Deal found 5/26![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 5/26. 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
Mon 8/311:05 pm
ORF
- JAN
2 stops5h 55m
Southwest
Deal found 5/26![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 5/26. 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 10/2712:00 pm
JAN
- ORF
2 stops25h 16m
United Airlines
Sat 10/316:00 am
ORF
- JAN
2 stops10h 53m
United Airlines
Deal found 5/26![United Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 5/26. 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 8/285:01 pm
JAN
- ORF
1 stop4h 00m
Delta
Mon 8/316:23 am
ORF
- JAN
1 stop4h 20m
Delta
Deal found 5/26![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 5/29. 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 9/175:55 am
JAN
- ORF
2 stops11h 00m
Southwest
Sun 9/206:20 am
ORF
- JAN
2 stops12h 40m
Southwest
Deal found 5/29![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 5/30. 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.
Mon 6/2911:25 am
JAN
- ORF
2 stops11h 00m
Southwest
Sat 7/47:10 am
ORF
- JAN
2 stops9h 05m
Southwest
Deal found 5/30![Southwest logo]()
$423
This Southwest deal was found by Cheapflights users on 5/29. 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 7/911:25 am
JAN
- ORF
2 stops6h 10m
Southwest
Sat 7/117:30 am
ORF
- JAN
2 stops12h 05m
Southwest
Deal found 5/29![Southwest logo]()
$451
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated May 31, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated May 31, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/29. 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 6/65:35 am
JAN
- ORF
1 stop6h 28m
Delta
Sat 6/131:57 pm
ORF
- JAN
1 stop5h 18m
Delta
Deal found 5/29![Delta logo]()
$618
This Southwest deal was found by Cheapflights users on 5/29. 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 6/612:20 pm
JAN
- ORF
2 stops9h 45m
Southwest
Sat 6/1310:05 am
ORF
- JAN
1 stop9h 30m
Southwest
Deal found 5/29![Southwest logo]()
$695
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Mon 6/85:15 am
JAN
- ORF
1 stop4h 20m
American Airlines
Fri 6/128:18 pm
ORF
- JAN
1 stop4h 36m
American Airlines
Deal found 5/28![American Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 5/28. 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.
Mon 6/811:25 am
JAN
- ORF
2 stops9h 35m
Southwest
Thu 6/119:55 am
ORF
- JAN
2 stops13h 00m
Southwest
Deal found 5/28![Southwest logo]()
$670
This Southwest deal was found by Cheapflights users on 5/28. 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.
Mon 6/811:25 am
JAN
- ORF
2 stops9h 35m
Southwest
Fri 6/129:55 am
ORF
- JAN
2 stops10h 50m
Southwest
Deal found 5/28![Southwest logo]()
$724
This Delta deal was found by Cheapflights users on 5/29. 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.
Mon 6/83:06 pm
JAN
- ORF
1 stop5h 36m
Delta
Thu 6/114:43 pm
ORF
- JAN
1 stop4h 57m
Delta
Deal found 5/29![Delta logo]()
$749
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Mon 6/85:15 am
JAN
- ORF
2 stops8h 53m
American Airlines
Thu 6/116:32 pm
ORF
- JAN
1 stop6h 22m
American Airlines
Deal found 5/29![American Airlines logo]()
$754
This United Airlines deal was found by Cheapflights users on 5/29. 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 6/132:07 pm
JAN
- ORF
1 stop7h 24m
United Airlines
Wed 6/176:15 am
ORF
- JAN
1 stop6h 09m
United Airlines
Deal found 5/29![United Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 5/30. 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.
Mon 6/2911:25 am
JAN
- ORF
2 stops11h 00m
Southwest
Sat 7/48:40 am
ORF
- JAN
1 stop7h 35m
Southwest
Deal found 5/30![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 5/30. 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.
Mon 6/296:00 am
JAN
- ORF
1 stop5h 52m
Delta
Sat 7/410:58 am
ORF
- JAN
1 stop6h 56m
Delta
Deal found 5/30![Delta logo]()
$471
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 May 31, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated May 31, 2026.
This Delta deal was found by Cheapflights users on 5/29. 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.
Mon 6/157:00 pm
JAN
- ORF
1 stop4h 45m
Delta
Deal found 5/29![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 5/29. 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.
Mon 6/1511:25 am
JAN
- ORF
2 stops6h 10m
Southwest
Deal found 5/29![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 5/27. 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 6/55:05 pm
JAN
- ORF
1 stop6h 13m
Delta
Deal found 5/27![Delta logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 5/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:04 pm
JAN
- ORF
3 stops51h 00m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$646
This United Airlines deal was found by Cheapflights users on 5/27. 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 6/67:10 am
JAN
- ORF
2 stops13h 26m
United Airlines
Deal found 5/27![United Airlines logo]()
$684
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:05 pm
JAN
- ORF
3 stops26h 59m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$689
This United Airlines deal was found by Cheapflights users on 5/27. 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 6/55:10 pm
JAN
- ORF
2 stops27h 26m
United Airlines
Deal found 5/27![United Airlines logo]()
$690
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 May 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (American Airlines) |
One-way from | $244 (Delta) |
Popular in | March |
Cheapest in | August |
Average price | $500 |
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 May 31, 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
3:03 pm-10:11 pm
1 stop6h 08m
Norfolk
Sun 9/20
5:02 pm-11:08 pm
1 stop7h 06m
$391
Quickest round-trip
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 8/28
5:01 pm-10:01 pm
1 stop4h 00m
Norfolk
Mon 8/31
6:23 am-9:43 am
1 stop4h 20m
$391
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 8/28
5:55 am-5:55 pm
2 stops11h 00m
Norfolk
Mon 8/31
1:05 pm-6:00 pm
2 stops5h 55m
$401
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 9/17
5:55 am-5:55 pm
2 stops11h 00m
Norfolk
Sun 9/20
6:20 am-6:00 pm
2 stops12h 40m
$409
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Mon 6/29
11:25 am-11:25 pm
2 stops11h 00m
Norfolk
Sat 7/4
7:10 am-3:15 pm
2 stops9h 05m
$423
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 7/9
11:25 am-6:35 pm
2 stops6h 10m
Norfolk
Sat 7/11
7:30 am-6:35 pm
2 stops12h 05m
$451
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Tue 10/27
12:00 pm-2:16 pm
2 stops25h 16m
Norfolk
Sat 10/31
6:00 am-3:53 pm
2 stops10h 53m
$541
Cheapest one-way
Quickest one-way
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Mon 6/15
7:00 pm-12:45 am
1 stop4h 45m
$244
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Mon 6/15
11:25 am-6:35 pm
2 stops6h 10m
$249
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Sat 6/6
5:00 pm-12:18 am
1 stop6h 18m
$375
Showing 1-10 of 13 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 May 31, 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
Food
7.2
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Food
7.2
Comfort
7.8
Overall
7.9
Crew
8.5
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 May 31, 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 May 31, 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 May 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$406 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$426 | FlexibilityNo cancel fee | On-time71% |