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Chesapeake

$259+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$259
(Delta)

Popular in

January

Cheapest in

February

Average price

$356
From Jackson-Evers Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($146 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 August 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 10/71:01 pmJAN - ORF
1 stop4h 36mDelta
Sun 10/125:24 amORF - JAN
1 stop4h 06mDelta
Deal found 8/13$259
This Southwest deal was found by Cheapflights users on 8/14. 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.
Mon 9/222:10 pmJAN - ORF
1 stop7h 40mSouthwest
Fri 9/269:45 amORF - JAN
1 stop9h 15mSouthwest
Deal found 8/14$270
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:55 pmJAN - ORF
1 stop4h 30mSouthwest
Fri 10/2410:05 amORF - JAN
2 stops10h 20mSouthwest
Deal found 8/13$299
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:43 pmJAN - ORF
1 stop4h 11mAmerican Airlines
Fri 10/101:03 pmORF - JAN
1 stop6h 15mAmerican Airlines
Deal found 8/13$338
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/74:00 pmJAN - ORF
1 stop4h 50mSouthwest
Sun 10/128:35 amORF - JAN
2 stops11h 50mSouthwest
Deal found 8/13$343
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:55 pmJAN - ORF
1 stop4h 30mSouthwest
Fri 10/105:30 amORF - JAN
2 stops12h 50mSouthwest
Deal found 8/13$354
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:28 pmJAN - ORF
1 stop6h 26mAmerican Airlines
Mon 10/204:00 pmORF - JAN
1 stop6h 36mAmerican Airlines
Deal found 8/13$367

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 14, 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

Mon 10/20

5:55 pm-11:25 pm

1 stop4h 30m

Norfolk

Fri 10/24

1:10 pm-5:20 pm

1 stop5h 10m

$259

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Tue 10/7

1:01 pm-6:37 pm

1 stop4h 36m

Norfolk

Sun 10/12

5:24 am-8:30 am

1 stop4h 06m

$259

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Mon 9/22

2:10 pm-10:50 pm

1 stop7h 40m

Norfolk

Fri 9/26

9:45 am-6:00 pm

1 stop9h 15m

$270

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Mon 10/6

6:43 pm-11:54 pm

1 stop4h 11m

Norfolk

Fri 10/10

1:03 pm-6:18 pm

1 stop6h 15m

$338

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Tue 10/7

4:00 pm-9:50 pm

1 stop4h 50m

Norfolk

Sun 10/12

8:35 am-7:25 pm

2 stops11h 50m

$343

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Mon 10/6

5:55 pm-11:25 pm

1 stop4h 30m

Norfolk

Fri 10/10

5:30 am-5:20 pm

2 stops12h 50m

$354

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 10/17

4:28 pm-11:54 pm

1 stop6h 26m

Norfolk

Mon 10/20

4:00 pm-9:36 pm

1 stop6h 36m

$367

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Wed 8/20

11:31 am-6:40 pm

1 stop6h 09m

$318

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Wed 8/20

11:58 am-10:03 pm

2 stops9h 05m

$323

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 8/22

5:59 pm-12:22 am

1 stop5h 23m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 15 results
1
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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 August 14, 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 August 14, 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
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$270Average$430FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$391FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$351Average$396FlexibilityNo cancel feeOn-time63%

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