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Chesapeake

$321+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
May 10 — May 171
Sun 5/10
Sun 5/17
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 April 10, 2026.

This American Airlines deal was found by Cheapflights users on 4/7. 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 6/104:21 pm
JAN
-
ORF
1 stop6h 20m
American Airlines
Wed 6/171:26 pm
ORF
-
JAN
1 stop7h 33m
American Airlines
Deal found 4/7$335
This Delta deal was found by Cheapflights users on 4/9. 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 6/1210:48 am
JAN
-
ORF
1 stop5h 22m
Delta
Wed 6/178:00 am
ORF
-
JAN
1 stop5h 10m
Delta
Deal found 4/9$371
This Delta deal was found by Cheapflights users on 4/4. 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.
Thu 7/2312:50 pm
JAN
-
ORF
1 stop5h 04m
Delta
Tue 7/286:17 pm
ORF
-
JAN
1 stop5h 52m
Delta
Deal found 4/4$407
This Southwest deal was found by Cheapflights users on 4/9. 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 6/1211:25 am
JAN
-
ORF
2 stops11h 00m
Southwest
Wed 6/173:40 pm
ORF
-
JAN
1 stop4h 05m
Southwest
Deal found 4/9$412
This Delta deal was found by Cheapflights users on 4/9. 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 5/810:51 am
JAN
-
ORF
1 stop5h 30m
Delta
Sun 5/175:20 am
ORF
-
JAN
1 stop4h 37m
Delta
Deal found 4/9$417
This American Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 5/16:00 am
JAN
-
ORF
1 stop6h 38m
American Airlines
Sun 5/37:58 pm
ORF
-
JAN
1 stop5h 01m
American Airlines
Deal found 4/8$427
This Southwest deal was found by Cheapflights users on 4/8. 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.
Fri 5/112:15 pm
JAN
-
ORF
2 stops8h 20m
Southwest
Sun 5/310:20 am
ORF
-
JAN
2 stops12h 40m
Southwest
Deal found 4/8$461
This Southwest deal was found by Cheapflights users on 4/9. 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 5/812:15 pm
JAN
-
ORF
2 stops9h 40m
Southwest
Sun 5/1710:20 am
ORF
-
JAN
2 stops12h 40m
Southwest
Deal found 4/9$484
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Fri 4/241:58 pm
JAN
-
ORF
1 stop7h 25m
United Airlines
Tue 4/286:08 am
ORF
-
JAN
1 stop6h 03m
United Airlines
Deal found 4/9$487
This Southwest deal was found by Cheapflights users on 4/9. 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 4/245:45 am
JAN
-
ORF
2 stops10h 05m
Southwest
Tue 4/2812:45 pm
ORF
-
JAN
1 stop5h 45m
Southwest
Deal found 4/9$492
This United Airlines deal was found by Cheapflights users on 4/7. 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 4/281:58 pm
JAN
-
ORF
1 stop7h 25m
United Airlines
Wed 4/296:08 am
ORF
-
JAN
1 stop6h 03m
United Airlines
Deal found 4/7$495

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 April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(American Airlines)

One-way from

$321
(American Airlines)

Popular in

March

Cheapest in

October

Average price

$516
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
One-way flight from Jackson-Evers Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($189 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 10, 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

Price

Cheapest round-trip

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Thu 7/23

12:50 pm-6:54 pm

1 stop5h 04m

Norfolk

Tue 7/28

6:17 pm-11:09 pm

1 stop5h 52m

$407

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Thu 7/23

5:10 am-2:50 pm

2 stops8h 40m

Norfolk

Tue 7/28

3:40 pm-6:45 pm

1 stop4h 05m

$412

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 6/12

11:25 am-11:25 pm

2 stops11h 00m

Norfolk

Wed 6/17

3:40 pm-6:45 pm

1 stop4h 05m

$412

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Sat 7/25

5:35 am-3:15 pm

2 stops8h 40m

Norfolk

Wed 7/29

3:40 pm-6:45 pm

1 stop4h 05m

$412
Quickest round-trip

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 5/8

10:51 am-5:21 pm

1 stop5h 30m

Norfolk

Sun 5/17

5:20 am-8:57 am

1 stop4h 37m

$417

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 8/28

5:55 am-3:10 pm

2 stops8h 15m

Norfolk

Sun 8/30

11:45 am-8:15 pm

2 stops9h 30m

$417

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 5/1

12:15 pm-9:35 pm

2 stops8h 20m

Norfolk

Sun 5/3

10:20 am-10:00 pm

2 stops12h 40m

$461

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Fri 4/24

1:58 pm-10:23 pm

1 stop7h 25m

Norfolk

Tue 4/28

6:08 am-11:11 am

1 stop6h 03m

$487

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Tue 4/28

1:58 pm-10:23 pm

1 stop7h 25m

Norfolk

Wed 4/29

6:08 am-11:11 am

1 stop6h 03m

$487

JacksonNorfolk

JAN - ORF

JANORF

Jackson-Evers Intl

Tue 5/12

1:58 pm-10:28 pm

1 stop7h 30m

Norfolk

Sat 5/16

6:10 am-11:16 am

1 stop6h 06m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

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 April is currently the most expensive (average of $516). 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.

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 April 10, 2026.
Read reviews from past customers who have flown 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.
Delta
7.9
Good
8,399 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,399 reviews
Delta
7.9
Good
8,399 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,564 reviews
Delta
7.9
Good
8,399 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 2 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 5h 04m. Delta provides one of the quickest options available for as low as $407. 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 April is currently the most expensive (average of $516). 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 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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$414FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$293Average$385FlexibilityNo cancel feeOn-time71%

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