$300+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Sep 5 — Sep 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
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 August 6, 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 August 6, 2026.
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Fr 9/113:27 pm -
1 stop4h 21m
So 9/138:09 pm -
1 stop4h 41m
Deal found 8/4![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/4. 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.
Sa 12/195:35 pm -
1 stop5h 39m
Di 12/296:55 am -
1 stop5h 27m
Deal found 8/4![Delta logo]()
$378
This Delta deal was found by Cheapflights users on 8/3. 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.
Do 10/153:33 pm -
1 stop3h 52m
So 10/185:30 am -
1 stop4h 03m
Deal found 8/3![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 8/3. 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.
Do 10/1512:00 pm -
2 stops8h 45m
So 10/186:20 am -
2 stops7h 00m
Deal found 8/3![Southwest logo]()
$414
This Delta deal was found by Cheapflights users on 8/5. 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.
So 10/47:04 pm -
1 stop4h 34m
So 10/117:00 am -
1 stop4h 25m
Deal found 8/5![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fr 9/412:40 pm -
2 stops8h 00m
So 9/66:45 am -
2 stops11h 00m
Deal found 8/4![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 8/5. 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.
So 10/45:45 am -
2 stops12h 05m
So 10/116:20 am -
2 stops7h 00m
Deal found 8/5![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 8/4. 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.
Sa 12/195:10 am -
2 stops10h 55m
Di 12/291:30 pm -
2 stops9h 45m
Deal found 8/4![Southwest logo]()
$444
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Do 10/156:45 pm -
1 stop4h 12m
So 10/181:37 pm -
1 stop5h 38m
Deal found 8/1![American Airlines logo]()
$447
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 August 6, 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 August 6, 2026.
This Delta deal was found by Cheapflights users on 8/3. 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.
Do 10/153:33 pm -
1 stop3h 52m
So 10/185:30 am -
1 stop4h 03m
Deal found 8/3![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 8/1. 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.
Do 10/1512:00 pm -
2 stops8h 25m
So 10/186:20 am -
2 stops7h 00m
Deal found 8/1![Southwest logo]()
$414
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Do 10/156:45 pm -
1 stop4h 12m
So 10/181:37 pm -
1 stop5h 38m
Deal found 8/1![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sa 9/269:20 am -
2 stops25h 55m
Di 9/296:00 am -
1 stop6h 27m
Deal found 8/1![United Airlines logo]()
$583
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sa 12/195:10 am -
2 stops10h 55m
Di 12/291:30 pm -
2 stops9h 45m
Deal found 8/3![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 8/3. 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.
Mo 8/175:01 pm -
1 stop7h 02m
Do 8/201:51 pm -
1 stop5h 29m
Deal found 8/3![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 8/4. 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.
Fr 8/217:00 pm -
1 stop5h 03m
So 8/235:23 am -
1 stop4h 06m
Deal found 8/4![Delta logo]()
$497
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fr 9/46:00 am -
1 stop14h 48m
Mo 9/147:25 pm -
1 stop4h 27m
Deal found 8/5![American Airlines logo]()
$603
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated August 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Fr 8/76:35 am -
1 stop4h 34m
Fr 8/287:23 pm -
1 stop4h 16m
Deal found 8/4![American Airlines logo]()
$576
This Delta deal was found by Cheapflights users on 8/3. 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.
Mo 8/175:01 pm -
1 stop7h 02m
Do 8/201:51 pm -
1 stop5h 29m
Deal found 8/3![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 8/3. 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.
Mo 8/175:55 am -
2 stops11h 00m
Do 8/201:55 pm -
1 stop5h 05m
Deal found 8/3![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fr 8/215:55 am -
2 stops11h 00m
So 8/231:30 pm -
2 stops7h 45m
Deal found 8/4![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fr 9/412:40 pm -
2 stops8h 00m
So 9/66:45 am -
2 stops11h 00m
Deal found 8/4![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fr 9/412:40 pm -
2 stops8h 00m
Mo 9/710:10 am -
2 stops11h 05m
Deal found 8/4![Southwest logo]()
$560
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Fr 9/412:01 pm -
2 stops8h 47m
Mo 9/147:25 pm -
1 stop4h 27m
Deal found 8/1![American Airlines logo]()
$568
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Fr 9/113:27 pm -
1 stop4h 21m
So 9/138:09 pm -
1 stop4h 41m
Deal found 8/4![American Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fr 9/115:55 am -
2 stops11h 00m
So 9/1311:45 am -
2 stops9h 35m
Deal found 8/4![Southwest logo]()
$531
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 August 6, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Southwest deal was found by Cheapflights users on 8/4. 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.
Di 8/111:30 pm -
2 stops7h 00m
Deal found 8/4![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 8/4. 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.
Di 8/119:15 am -
1 stop6h 53m
Deal found 8/4![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Di 8/116:35 am -
1 stop6h 27m
Deal found 8/4![American Airlines logo]()
$335
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Fr 8/142:05 pm -
1 stop7h 28m
Deal found 8/4![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fr 8/145:55 am -
2 stops11h 00m
Deal found 8/4![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Di 8/112:05 pm -
3 stops23h 12m
Deal found 8/4![United Airlines logo]()
$535
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Mi 8/122:05 pm -
3 stops23h 12m
Deal found 8/4![United Airlines logo]()
$579
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $371 (American Airlines) |
One-way from | $300 (Southwest) |
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 August 6, 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 Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Do 10/15
3:33 pm-8:25 pm
1 stop3h 52m
Norfolk
So 10/18
5:30 am-8:33 am
1 stop4h 03m
$391
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Do 10/15
12:00 pm-9:25 pm
2 stops8h 25m
Norfolk
So 10/18
6:20 am-12:20 pm
2 stops7h 00m
$414
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sa 12/19
5:10 am-5:05 pm
2 stops10h 55m
Norfolk
Di 12/29
1:30 pm-10:15 pm
2 stops9h 45m
$444
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Do 10/15
6:45 pm-11:57 pm
1 stop4h 12m
Norfolk
So 10/18
1:37 pm-6:15 pm
1 stop5h 38m
$447
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Mo 8/17
5:01 pm-1:03 am
1 stop7h 02m
Norfolk
Do 8/20
1:51 pm-6:20 pm
1 stop5h 29m
$497
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fr 8/21
7:00 pm-1:03 am
1 stop5h 03m
Norfolk
So 8/23
5:23 am-8:29 am
1 stop4h 06m
$497
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sa 9/26
9:20 am-12:15 pm
2 stops25h 55m
Norfolk
Di 9/29
6:00 am-11:27 am
1 stop6h 27m
$583
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fr 9/4
6:00 am-9:48 pm
1 stop14h 48m
Norfolk
Mo 9/14
7:25 pm-10:52 pm
1 stop4h 27m
$603
Cheapest one-way
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Di 8/11
1:30 pm-9:30 pm
2 stops7h 00m
$300
Quickest one-way
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Di 8/11
5:01 pm-10:01 pm
1 stop4h 00m
$305
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
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 August 6, 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.
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Crew
8.5
Comfort
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Jackson
Popular flights
Top destinations
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.
Search flights from Jackson to Chesapeake by cabin class
Find flights from Jackson to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jackson and Chesapeake flights
Browse other Jackson and Chesapeake flight options. Last updated on August 6, 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 August 6, 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 August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$427 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$377 | FlexibilityNo cancel fee | On-time71% |