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Chesapeake

$43+ Cheap flights from Jacksonville (JAX) 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — RIC
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chesapeake are usually found in May or June, booked 44 days in advance, depart on a Sunday or Thursday and return on a Thursday

Cheap flight deals from Jacksonville to Chesapeake

Keep the following information in mind while searching for Jacksonville to Chesapeake flight deals. Data was last updated July 16, 2025.

Round-trip from

$77
(Cheapflightsfares)

One-way from

$43
(Cheapflightsfares)

Popular in

November

Cheapest in

May

Average price

$153
From Jacksonville to Chesapeake
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One-way flight from Jacksonville to Chesapeake
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Highest demand for flights based on searches. 25% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Jacksonville to Chesapeake

Cheapest flights from Jacksonville to Chesapeake
Explore the most affordable flight options available from Jacksonville to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/33:28 pmJAX - ORF
Nonstop1h 36mAllegiant Air
Sun 8/105:54 pmORF - JAX
Nonstop1h 42mAllegiant Air
Deal found 7/16$77
This Breeze Airways deal was found by Cheapflights users on 7/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/122:08 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Tue 8/1911:40 amORF - JAX
Nonstop1h 48mBreeze Airways
Deal found 7/15$98
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/313:28 pmJAX - ORF
Nonstop1h 36mMultiple Airlines
Wed 8/68:05 amORF - JAX
Nonstop1h 48mMultiple Airlines
Deal found 7/14$103
This Delta deal was found by Cheapflights users on 7/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/38:25 pmJAX - ORF
1 stop4h 14mDelta
Sun 8/106:00 amORF - JAX
1 stop5h 20mDelta
Deal found 7/16$237
This American Airlines deal was found by Cheapflights users on 7/14. 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.
Sun 7/2011:06 amJAX - ORF
1 stop5h 57mAmerican Airlines
Thu 7/245:03 amORF - JAX
1 stop5h 13mAmerican Airlines
Deal found 7/14$248

Cheapflights Fare Finder

Customize your flight search to find flights from Jacksonville 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 July 16, 2025.
Use the filters below to find and compare flights from Jacksonville to Chesapeake that are best for you.

Fly from

Jacksonville

Fly to

Chesapeake

Route

Depart

Return

Price

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Sun 8/3

3:28 pm-5:04 pm

Nonstop1h 36m

Norfolk

Sun 8/10

5:54 pm-7:36 pm

Nonstop1h 42m

$77

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Tue 8/12

2:08 pm-3:46 pm

Nonstop1h 38m

Norfolk

Tue 8/19

11:40 am-1:28 pm

Nonstop1h 48m

$98

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Thu 7/31

3:28 pm-5:04 pm

Nonstop1h 36m

Norfolk

Wed 8/6

8:05 am-9:53 am

Nonstop1h 48m

$103

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Sun 8/3

8:25 pm-12:39 am

1 stop4h 14m

Norfolk

Sun 8/10

6:00 am-11:20 am

1 stop5h 20m

$237

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Tue 8/12

6:15 am-3:00 pm

2 stops8h 45m

Norfolk

Tue 8/19

2:20 pm-8:40 pm

1 stop6h 20m

$242

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Thu 7/31

3:28 pm-5:04 pm

Nonstop1h 36m

$43

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Sat 8/16

3:43 pm-5:21 pm

Nonstop1h 38m

$49

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Tue 7/29

9:55 am-5:02 pm

1 stop7h 07m

$116

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Sun 10/12

5:30 am-9:02 am

1 stop3h 32m

$119

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 8/13

6:15 am-3:00 pm

2 stops8h 45m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Showing 1-10 of 12 results
1
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Best time to book a flight from Jacksonville to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Jacksonville 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 Jacksonville to Chesapeake

How far ahead should I book a flight from Jacksonville to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Jacksonville to Chesapeake. Price data was last updated on July 11, 2025.

To ensure you get the cheapest price possible for a flight from Jacksonville to Chesapeake, you should look to book at least 44 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Jacksonville to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Jacksonville to Chesapeake (average of $281). Flying from Jacksonville 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 JAX to C6E?

Find hourly flight availability from Jacksonville 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 July 16, 2025.

When flying from Jacksonville to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Jacksonville to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Jacksonville to Chesapeake. Price data was last updated on July 13, 2025.

Travelers seeking maximum savings on their Jacksonville to Chesapeake flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 16, 2025.
See what other customers who have flown with Southwest, Delta, and Breeze Airways from Jacksonville to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Breeze Airways
8.0
Very good
187 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,863 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,909 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville 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 Jacksonville to Chesapeake?

    Jacksonville (JAX), located 11.2 mi from the city center, is the airport you fly out of when you book flights from Jacksonville to Chesapeake. 6 airlines have flights from Jacksonville to Chesapeake on a regular basis. Booking flights from Jacksonville to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • What are the cheapest airlines to fly from Jacksonville to Chesapeake one-way?

    $43 is the cheapest one-way deal found within the past few days, from Allegiant Air. You may also be able to find cheap deals on Breeze Airways and JetBlue, with prices starting from $49 and $116, respectively.

  • What are the cheapest flights from Jacksonville to Chesapeake?

    The cheapest flight price from Jacksonville to Chesapeake is $74. On average you can expect to pay $154. The most popular route, (Jacksonville - Norfolk), can usually be booked for $77.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jacksonville 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 Jacksonville to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Jacksonville to Chesapeake (average of $281). Flying from Jacksonville 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 6 airlines flying from Jacksonville to Chesapeake

Discover the top 6 airlines that operate flights from Jacksonville 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 July 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$45Average$81FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$95Average$164FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$148Average$250FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$300FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$185Average$349FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$283Average$372FlexibilityNo cancel feeOn-time63%

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