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Chesapeake

$295+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Jan 5 — Jan 121
Mon 1/5
Mon 1/12
1 adult, Economy
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Cheap 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 December 6, 2025.

This Southwest deal was found by Cheapflights users on 12/2. 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 12/243:40 pmJAN - ORF
1 stop5h 20mSouthwest
Tue 1/612:40 pmORF - JAN
1 stop5h 55mSouthwest
Deal found 12/2$337
This Delta deal was found by Cheapflights users on 12/3. 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.
Wed 12/1711:17 amJAN - ORF
1 stop6h 17mDelta
Sun 12/285:23 amORF - JAN
1 stop4h 13mDelta
Deal found 12/3$362
This Delta deal was found by Cheapflights users on 12/5. 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.
Wed 12/243:00 pmJAN - ORF
1 stop5h 52mDelta
Sun 12/285:23 amORF - JAN
1 stop4h 13mDelta
Deal found 12/5$503
This Southwest deal was found by Cheapflights users on 12/3. 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.
Wed 12/171:10 pmJAN - ORF
2 stops7h 50mSouthwest
Sun 12/283:25 pmORF - JAN
1 stop5h 20mSouthwest
Deal found 12/3$505
This United Airlines deal was found by Cheapflights users on 12/2. 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 12/2412:01 pmJAN - ORF
3 stops10h 40mUnited Airlines
Tue 1/64:45 pmORF - JAN
2 stops24h 17mUnited Airlines
Deal found 12/2$548
This Southwest deal was found by Cheapflights users on 12/5. 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.
Wed 12/243:40 pmJAN - ORF
1 stop5h 20mSouthwest
Sun 12/2810:05 amORF - JAN
2 stops10h 40mSouthwest
Deal found 12/5$549
This Southwest deal was found by Cheapflights users on 12/4. 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.
Thu 12/1811:50 amJAN - ORF
1 stop6h 50mSouthwest
Sun 12/211:30 pmORF - JAN
2 stops9h 35mSouthwest
Deal found 12/4$562

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 December 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$295
(United Airlines)

Popular in

January

Cheapest in

February
Provider with most accurate pricing for Jackson-Evers Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson-Evers Intl-Norfolk flights.
Search Deals
From Jackson-Evers Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($219 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($60 potential savings vs. average RT price).
Search Deals

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 December 6, 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

Sat 1/17

2:00 pm-10:30 pm

1 stop7h 30m

Norfolk

Wed 1/21

6:00 am-1:22 pm

1 stop8h 22m

$295

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Sat 2/21

2:03 pm-10:28 pm

1 stop7h 25m

Norfolk

Wed 2/25

6:00 am-1:26 pm

1 stop8h 26m

$387

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 1/2

5:32 pm-10:56 pm

1 stop4h 24m

Norfolk

Fri 1/9

5:20 am-11:17 am

1 stop6h 57m

$463

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Wed 12/24

3:00 pm-9:52 pm

1 stop5h 52m

Norfolk

Sun 12/28

5:23 am-8:36 am

1 stop4h 13m

$503

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Wed 12/24

3:40 pm-10:00 pm

1 stop5h 20m

Norfolk

Sun 12/28

10:05 am-7:45 pm

2 stops10h 40m

$549

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 1/2

1:13 pm-9:31 pm

1 stop7h 18m

Norfolk

Fri 1/9

3:06 pm-11:45 pm

2 stops9h 39m

$565

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Thu 12/18

3:31 pm-10:30 pm

1 stop5h 59m

Norfolk

Sun 12/21

3:45 pm-7:54 pm

1 stop5h 09m

$628

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 12/19

6:05 pm-11:35 pm

1 stop4h 30m

Norfolk

Sat 12/20

3:10 pm-10:30 pm

2 stops8h 20m

$663

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 12/12

6:44 am-2:44 pm

1 stop7h 00m

$349

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 12/12

5:15 pm-11:13 pm

3 stops28h 58m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

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, October is the cheapest month in which you can book a flight from Jackson, Mississippi to Chesapeake (average of $184). Flying from Jackson, Mississippi to Chesapeake in November is currently the most expensive (average of $372). 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 December 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Jackson, Mississippi to Chesapeake at noon. If you’re flexible enough to do this you can expect to save up to 32% on your trip compared to booking a flight in the morning.

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 December 6, 2025.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines 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
4,251 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,009 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,043 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 24m. United Airlines provides one of the quickest options available for as low as $463. 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, October is the cheapest month in which you can book a flight from Jackson, Mississippi to Chesapeake (average of $184). Flying from Jackson, Mississippi to Chesapeake in November is currently the most expensive (average of $372). 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.

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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 December 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$250Average$371FlexibilityNo cancel feeOn-time63%
DeltaCheapest$270Average$412FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$292Average$379FlexibilityNo cancel feeOn-time71%

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