$159+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Find cheap flights from Jackson to Chesapeake with Cheapflights
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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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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 July 2, 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 2, 2026.
This Delta deal was found by Cheapflights users on 7/1. 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
JAN
- ORF
1 stop4h 29m
Delta
Sun 9/205:30 am
ORF
- JAN
1 stop3h 59m
Delta
Deal found 7/1![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 6/28. 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.
Fri 8/215:55 am
JAN
- ORF
2 stops8h 15m
Southwest
Mon 8/241:55 pm
ORF
- JAN
1 stop5h 05m
Southwest
Deal found 6/28![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 6/30. 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 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
Sun 8/28:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/30![American Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 7/1. 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 7/1![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 6/29. 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.
Fri 7/247:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Mon 7/275:15 am
ORF
- JAN
1 stop5h 45m
Delta
Deal found 6/29![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 9/45:55 am
JAN
- ORF
2 stops8h 15m
Southwest
Sun 9/136:20 am
ORF
- JAN
2 stops12h 45m
Southwest
Deal found 6/29![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:01 pm
JAN
- ORF
1 stop7h 02m
Delta
Mon 9/145:30 am
ORF
- JAN
1 stop3h 59m
Delta
Deal found 6/28![Delta logo]()
$481
This Delta deal was found by Cheapflights users on 6/30. 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.
Wed 7/1512:50 pm
JAN
- ORF
1 stop5h 03m
Delta
Sun 7/196:20 am
ORF
- JAN
1 stop4h 40m
Delta
Deal found 6/30![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 7/3011:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 8/39:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/30![Southwest logo]()
$489
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 2, 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 2, 2026.
This Delta deal was found by Cheapflights users on 7/1. 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
JAN
- ORF
1 stop4h 29m
Delta
Sun 9/205:30 am
ORF
- JAN
1 stop3h 59m
Delta
Deal found 7/1![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 6/28. 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.
Fri 8/215:55 am
JAN
- ORF
2 stops8h 15m
Southwest
Mon 8/241:55 pm
ORF
- JAN
1 stop5h 05m
Southwest
Deal found 6/28![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 7/1. 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 7/1![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 6/27. 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 9/45:01 pm
JAN
- ORF
1 stop7h 02m
Delta
Mon 9/1410:52 am
ORF
- JAN
1 stop4h 25m
Delta
Deal found 6/27![Delta logo]()
$481
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 9/45:55 am
JAN
- ORF
2 stops8h 15m
Southwest
Sun 9/136:20 am
ORF
- JAN
2 stops12h 45m
Southwest
Deal found 6/29![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 6/28. 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.
Fri 9/45:55 am
JAN
- ORF
2 stops8h 15m
Southwest
Mon 9/710:10 am
ORF
- JAN
2 stops11h 00m
Southwest
Deal found 6/28![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 7/3011:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 8/39:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/30![Southwest logo]()
$489
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated July 2, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/30. 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.
Wed 7/1512:50 pm
JAN
- ORF
1 stop5h 03m
Delta
Sun 7/196:20 am
ORF
- JAN
1 stop4h 40m
Delta
Deal found 6/30![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 6/30. 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.
Wed 7/1512:20 pm
JAN
- ORF
2 stops8h 35m
Southwest
Sun 7/191:25 pm
ORF
- JAN
2 stops9h 40m
Southwest
Deal found 6/30![Southwest logo]()
$561
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:53 am
JAN
- ORF
2 stops9h 18m
American Airlines
Sun 7/198:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/30![American Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 6/29. 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.
Fri 7/247:10 pm
JAN
- ORF
1 stop4h 35m
Delta
Mon 7/275:15 am
ORF
- JAN
1 stop5h 45m
Delta
Deal found 6/29![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/30. 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 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
Sun 8/28:20 pm
ORF
- JAN
1 stop4h 28m
American Airlines
Deal found 6/30![American Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 7/3011:25 am
JAN
- ORF
2 stops11h 05m
Southwest
Mon 8/39:55 am
ORF
- JAN
2 stops13h 05m
Southwest
Deal found 6/30![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 7/3011:25 am
JAN
- ORF
2 stops6h 10m
Southwest
Sun 8/21:25 pm
ORF
- JAN
2 stops9h 40m
Southwest
Deal found 6/30![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 6/28. 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.
Fri 8/215:55 am
JAN
- ORF
2 stops8h 15m
Southwest
Mon 8/241:55 pm
ORF
- JAN
1 stop5h 05m
Southwest
Deal found 6/28![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 7/1. 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 7/1![Southwest logo]()
$412
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 2, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Delta deal was found by Cheapflights users on 6/29. 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.
Tue 7/2110:46 am
JAN
- ORF
1 stop7h 07m
Delta
Deal found 6/29![Delta logo]()
$159
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/102:07 pm
JAN
- ORF
1 stop7h 23m
United Airlines
Deal found 6/30![United Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 6/29. 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.
Tue 7/2112:20 pm
JAN
- ORF
2 stops9h 20m
Southwest
Deal found 6/29![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 7/1. 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 stops9h 20m
Southwest
Deal found 7/1![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 7/1. 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 7/812:50 pm
JAN
- ORF
1 stop5h 03m
Delta
Deal found 7/1![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 7/92:07 pm
JAN
- ORF
1 stop7h 23m
United Airlines
Deal found 7/1![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/97:20 am
JAN
- ORF
2 stops6h 46m
American Airlines
Deal found 7/1![American Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Tue 7/219:20 am
JAN
- ORF
3 stops13h 24m
United Airlines
Deal found 6/29![United Airlines logo]()
$568
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 7/89:20 am
JAN
- ORF
3 stops13h 24m
United Airlines
Deal found 7/1![United Airlines logo]()
$782
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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (Delta) |
One-way from | $159 (Delta) |
Popular in | March |
Cheapest in | October |
Average price | $450 |
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 2, 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
Quickest round-trip
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Thu 9/17
7:04 pm-12:33 am
1 stop4h 29m
Norfolk
Sun 9/20
5:30 am-8:29 am
1 stop3h 59m
$381
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 8/21
5:55 am-3:10 pm
2 stops8h 15m
Norfolk
Mon 8/24
1:55 pm-6:00 pm
1 stop5h 05m
$386
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
$417
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
5:55 am-3:10 pm
2 stops8h 15m
Norfolk
Sun 9/13
6:20 am-6:05 pm
2 stops12h 45m
$461
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
5:55 am-3:10 pm
2 stops8h 15m
Norfolk
Mon 9/7
10:10 am-8:10 pm
2 stops11h 00m
$461
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Fri 9/4
5:01 pm-1:03 am
1 stop7h 02m
Norfolk
Mon 9/14
10:52 am-2:17 pm
1 stop4h 25m
$481
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
$489
Cheapest one-way
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Tue 7/21
10:46 am-6:53 pm
1 stop7h 07m
$159
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Mon 8/10
2:07 pm-10:30 pm
1 stop7h 23m
$218
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Tue 7/21
12:20 pm-10:40 pm
2 stops9h 20m
$219
Showing 1-10 of 15 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 2, 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
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Comfort
7.8
Boarding
8.1
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 2, 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 2, 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$414 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$426 | FlexibilityNo cancel fee | On-time71% |