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Chesapeake

$360+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 16, 2025.

Round-trip from

$360
(Delta)

Popular in

January

Cheapest in

February

Average price

$382
From Jackson-Evers Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($145 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Jackson to Chesapeake

Cheapest flights from Jackson to Chesapeake
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 16, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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 12/256:00 amJAN - ORF
1 stop4h 20mDelta
Sat 1/37:00 amORF - JAN
1 stop7h 23mDelta
Deal found 9/14$360
This Southwest deal was found by Cheapflights users on 9/14. 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 12/256:25 amJAN - ORF
2 stops10h 10mSouthwest
Sat 1/312:55 pmORF - JAN
1 stop6h 00mSouthwest
Deal found 9/14$410
This Delta deal was found by Cheapflights users on 9/14. 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 9/307:46 amJAN - ORF
1 stop5h 45mDelta
Sun 10/55:30 amORF - JAN
1 stop4h 03mDelta
Deal found 9/14$427
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/3012:08 pmJAN - ORF
2 stops9h 52mAmerican Airlines
Sun 10/57:04 pmORF - JAN
1 stop4h 27mAmerican Airlines
Deal found 9/14$432
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/31:38 pmJAN - ORF
2 stops7h 59mAmerican Airlines
Mon 10/63:18 pmORF - JAN
2 stops7h 18mAmerican Airlines
Deal found 9/14$437
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 10/17:46 amJAN - ORF
1 stop4h 03mDelta
Sun 10/55:30 amORF - JAN
1 stop4h 03mDelta
Deal found 9/15$447
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:10 amJAN - ORF
2 stops7h 54mAmerican Airlines
Sun 10/57:04 pmORF - JAN
1 stop4h 27mAmerican Airlines
Deal found 9/15$452
This Southwest deal was found by Cheapflights users on 9/14. 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 9/262:10 pmJAN - ORF
1 stop7h 40mSouthwest
Sun 9/288:30 amORF - JAN
1 stop6h 55mSouthwest
Deal found 9/14$588
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/268:19 amJAN - ORF
1 stop5h 51mAmerican Airlines
Fri 9/267:04 pmORF - JAN
1 stop4h 27mAmerican Airlines
Deal found 9/14$661
This Delta deal was found by Cheapflights users on 9/13. 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 9/2010:05 amJAN - ORF
1 stop5h 45mDelta
Sun 9/213:36 pmORF - JAN
1 stop6h 01mDelta
Deal found 9/13$667

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 September 16, 2025.
Use the filters below to find and compare flights from Jackson to Chesapeake that are best for you.

Fly from

Jackson

Fly to

Chesapeake

Route

Depart

Return

Price

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Thu 12/25

6:00 am-11:20 am

1 stop4h 20m

Norfolk

Sat 1/3

7:00 am-1:23 pm

1 stop7h 23m

$360

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Thu 12/25

6:25 am-5:35 pm

2 stops10h 10m

Norfolk

Sat 1/3

12:55 pm-5:55 pm

1 stop6h 00m

$410

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Tue 9/30

7:46 am-2:31 pm

1 stop5h 45m

Norfolk

Sun 10/5

5:30 am-8:33 am

1 stop4h 03m

$427

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Tue 9/30

12:08 pm-11:00 pm

2 stops9h 52m

Norfolk

Sun 10/5

7:04 pm-10:31 pm

1 stop4h 27m

$432

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 10/3

5:55 pm-11:25 pm

1 stop4h 30m

Norfolk

Mon 10/6

5:30 am-5:20 pm

2 stops12h 50m

$432

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 10/3

1:38 pm-10:37 pm

2 stops7h 59m

Norfolk

Mon 10/6

3:18 pm-9:36 pm

2 stops7h 18m

$437

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Wed 10/1

7:46 am-12:49 pm

1 stop4h 03m

Norfolk

Sun 10/5

5:30 am-8:33 am

1 stop4h 03m

$447

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Wed 10/1

8:10 am-5:04 pm

2 stops7h 54m

Norfolk

Sun 10/5

7:04 pm-10:31 pm

1 stop4h 27m

$452

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 9/26

2:10 pm-10:50 pm

1 stop7h 40m

Norfolk

Sun 9/28

8:30 am-2:25 pm

1 stop6h 55m

$588

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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.
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

What is the cheapest month to book a flight from Jackson, Mississippi to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Jackson, Mississippi to Chesapeake (average of $281). Flying from Jackson, Mississippi to Chesapeake in March is currently the most expensive (average of $351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from JAN to C6E?

Find hourly flight availability from Jackson to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Jackson, Mississippi to Chesapeake as you normally would.

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 16, 2025.
Read reviews from past customers who have flown Southwest and 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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly from for flights from Jackson to Chesapeake?

    Jackson-Evers Intl (JAN) is the airport you will fly out of if you book a flight from Jackson to Chesapeake. You should not have trouble finding flights to Chesapeake from Jackson-Evers Intl; the airport handles an average of 0 outbound flights to Chesapeake per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Jackson airport to Chesapeake. It is only a 6.3 mi journey to Jackson-Evers Intl (JAN) from Jackson’s city center.

  • How long is the flight from Jackson, Mississippi to Chesapeake?

    A quick flight from Jackson, Mississippi to Chesapeake can take about 4h 20m. Delta provides one of the quickest options available for as low as $360. There are 849 mi between Jackson, Mississippi and Chesapeake. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Jackson to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Jackson to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jackson to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jackson to Chesapeake.

  • Can I find deals for business class flights from Jackson to Chesapeake?

    Yes. Cheapflights offers flight deals from Jackson to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Jackson, Mississippi to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Jackson, Mississippi to Chesapeake (average of $281). Flying from Jackson, Mississippi to Chesapeake in March is currently the most expensive (average of $351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 3 airlines flying from Jackson to Chesapeake

Discover the top 3 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$270Average$412FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$292Average$391FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$301Average$396FlexibilityNo cancel feeOn-time63%

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