$149+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Oct 13 — Oct 201
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 September 13, 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 September 13, 2026.
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/610:01 am -
1 stop6h 06m
Mon 10/126:17 pm -
1 stop6h 38m
Deal found 9/8![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 9/8. 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 11/185:48 pm -
1 stop4h 34m
Sun 11/221:55 pm -
1 stop5h 05m
Deal found 9/8![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 9/8. 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 10/31:03 pm -
1 stop6h 10m
Sat 10/107:00 am -
1 stop5h 49m
Deal found 9/8![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 9/8. 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 11/186:30 am -
2 stops6h 55m
Sun 11/223:25 pm -
2 stops7h 40m
Deal found 9/8![Southwest logo]()
$395
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/126:45 pm -
1 stop4h 12m
Mon 10/196:17 pm -
1 stop6h 38m
Deal found 9/12![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 9/10. 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 9/235:35 am -
1 stop5h 27m
Tue 10/611:00 am -
1 stop4h 38m
Deal found 9/10![Delta logo]()
$453
This Southwest deal was found by Cheapflights users on 9/8. 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 10/612:55 pm -
2 stops8h 15m
Mon 10/129:55 am -
2 stops10h 55m
Deal found 9/8![Southwest logo]()
$471
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/2312:14 pm -
2 stops9h 26m
Tue 10/65:57 pm -
1 stop6h 28m
Deal found 9/10![American Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 9/10. 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 9/257:04 pm -
1 stop4h 31m
Tue 9/295:02 pm -
1 stop3h 47m
Deal found 9/10![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 9/10. 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 9/237:05 am -
2 stops9h 15m
Tue 10/67:10 am -
2 stops11h 50m
Deal found 9/10![Southwest logo]()
$509
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 September 13, 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 September 13, 2026.
This Delta deal was found by Cheapflights users on 9/8. 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 10/31:03 pm -
1 stop6h 10m
Sat 10/107:00 am -
1 stop5h 49m
Deal found 9/8![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 9/8. 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 11/186:30 am -
2 stops6h 55m
Sun 11/223:25 pm -
2 stops7h 40m
Deal found 9/8![Southwest logo]()
$395
This United Airlines deal was found by Cheapflights users on 9/10. 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 11/109:05 am -
2 stops13h 39m
Wed 11/116:15 am -
2 stops8h 04m
Deal found 9/10![United Airlines logo]()
$517
This American Airlines deal was found by Cheapflights users on 9/8. 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 9/233:27 pm -
1 stop6h 14m
Sun 9/278:09 pm -
1 stop4h 41m
Deal found 9/8![American Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 9/10. 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 9/237:05 am -
2 stops9h 15m
Tue 10/67:10 am -
2 stops11h 50m
Deal found 9/10![Southwest logo]()
$509
This American Airlines deal was found by Cheapflights users on 9/12. 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 9/188:16 am -
1 stop4h 43m
Fri 10/96:17 pm -
1 stop6h 38m
Deal found 9/12![American Airlines logo]()
$656
Last-minute flights from Jackson to ChesapeakeDiscover last-minute flight deals from Jackson to Chesapeake. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chesapeake. Data last updated September 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/10. 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 9/1211:08 am -
1 stop6h 11m
Sat 9/1912:40 pm -
1 stop4h 49m
Deal found 9/10![Delta logo]()
$589
This Delta deal was found by Cheapflights users on 9/10. 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 9/235:35 am -
1 stop5h 27m
Tue 10/611:00 am -
1 stop4h 38m
Deal found 9/10![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/2312:14 pm -
2 stops9h 26m
Tue 10/65:57 pm -
1 stop6h 28m
Deal found 9/10![American Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 9/10. 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 9/237:05 am -
2 stops9h 15m
Tue 10/67:10 am -
2 stops11h 50m
Deal found 9/10![Southwest logo]()
$509
This American Airlines deal was found by Cheapflights users on 9/8. 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 9/233:27 pm -
1 stop6h 14m
Sun 9/278:09 pm -
1 stop4h 41m
Deal found 9/8![American Airlines logo]()
$584
This Delta deal was found by Cheapflights users on 9/10. 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 9/257:04 pm -
1 stop4h 31m
Tue 9/295:02 pm -
1 stop3h 47m
Deal found 9/10![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 9/8. 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 10/31:03 pm -
1 stop6h 10m
Sat 10/107:00 am -
1 stop5h 49m
Deal found 9/8![Delta logo]()
$373
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/610:01 am -
1 stop6h 06m
Mon 10/126:17 pm -
1 stop6h 38m
Deal found 9/8![American Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 9/8. 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 10/612:55 pm -
2 stops8h 15m
Mon 10/129:55 am -
2 stops10h 55m
Deal found 9/8![Southwest logo]()
$471
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/126:45 pm -
1 stop4h 12m
Mon 10/196:17 pm -
1 stop6h 38m
Deal found 9/12![American Airlines logo]()
$417
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 September 13, 2026.
Search for one-way flight options from Jackson to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/610:01 am -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![American Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 9/8. 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 10/612:55 pm -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 9/8. 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 10/65:02 pm -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/65:20 pm -
3 stops29h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$405
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 September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (American Airlines) |
One-way from | $149 (American Airlines) |
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 7,457,451 searches. Data last updated September 13, 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 Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 10/6
12:55 pm-10:10 pm
2 stops8h 15m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$154
Quickest round-trip
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 10/6
5:02 pm-12:45 am
1 stop6h 43m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Sat 10/3
1:03 pm-8:13 pm
1 stop6h 10m
Norfolk
Sat 10/10
7:00 am-11:49 am
1 stop5h 49m
$373
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Wed 11/18
6:30 am-2:25 pm
2 stops6h 55m
Norfolk
Sun 11/22
3:25 pm-10:05 pm
2 stops7h 40m
$395
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 10/6
5:20 pm-11:44 pm
3 stops29h 24m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$405
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Wed 9/23
7:05 am-5:20 pm
2 stops9h 15m
Norfolk
Tue 10/6
7:10 am-6:00 pm
2 stops11h 50m
$509
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Tue 11/10
9:05 am-11:44 pm
2 stops13h 39m
Norfolk
Wed 11/11
6:15 am-1:19 pm
2 stops8h 04m
$517
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Wed 9/23
3:27 pm-10:41 pm
1 stop6h 14m
Norfolk
Sun 9/27
8:09 pm-11:50 pm
1 stop4h 41m
$584
JacksonNorfolk
JAN Jackson-Evers Intl - ORF Norfolk
JANORF
Jackson-Evers Intl
Fri 9/18
8:16 am-1:59 pm
1 stop4h 43m
Norfolk
Fri 10/9
6:17 pm-11:55 pm
1 stop6h 38m
$656
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 September 13, 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.
Comfort
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 September 13, 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 September 13, 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 7,457,451 searches. Data last updated September 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$426 | FlexibilityNo cancel fee | On-time71% |