$284+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — RIC
Jan 17 — Jan 241
1 adult, Economy
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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
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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 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 December 18, 2025.
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 18, 2025.
This Southwest deal was found by Cheapflights users on 12/16. 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 12/313:40 pmJAN - ORF
1 stop5h 20mSouthwest
Mon 1/511:35 amORF - JAN
1 stop9h 00mSouthwest
Deal found 12/16![Southwest logo]()
$468
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/317:00 amJAN - ORF
3 stops15h 41mUnited Airlines
Mon 1/56:20 amORF - JAN
2 stops14h 22mUnited Airlines
Deal found 12/16![United Airlines logo]()
$839
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:00 amJAN - ORF
2 stops15h 41mUnited Airlines
Sat 12/276:00 amORF - JAN
1 stop14h 42mUnited Airlines
Deal found 12/14![United Airlines logo]()
$1,154
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 18, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $442 (United Airlines) |
One-way from | $284 (United Airlines) |
Popular in | January |
Cheapest in | February |
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 18, 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 2/14
2:03 pm-10:28 pm
1 stop7h 25m
Norfolk
Wed 2/18
6:00 am-11:16 am
1 stop6h 16m
$442
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Wed 12/31
3:40 pm-10:00 pm
1 stop5h 20m
Norfolk
Mon 1/5
11:35 am-7:35 pm
1 stop9h 00m
$468
JacksonNorfolk
JAN - ORF
JANORF
Jackson-Evers Intl
Wed 1/7
2:00 pm-10:30 pm
1 stop7h 30m
$284
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 18, 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 18, 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.
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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Alternative routes for Jackson to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
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 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$371 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$292 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$294 | Average$429 | FlexibilityNo cancel fee | On-timeN/A |