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Chesapeake

$49+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — RIC
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chesapeake are usually found in May or June, booked 61 days in advance, depart on a Sunday or Thursday and return on a Sunday

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 September 17, 2025.

Round-trip from

$98
(Breeze Airways)

One-way from

$49
(Breeze Airways)

Popular in

December

Cheapest in

May

Average price

$143
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 ($62 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 September 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 September 17, 2025.

This Breeze Airways deal was found by Cheapflights users on 9/15. 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.
Fri 11/72:34 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Sun 11/97:15 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$98
This Breeze Airways deal was found by Cheapflights users on 9/15. 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.
Wed 10/12:52 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Fri 10/37:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$103
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:34 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Fri 11/77:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$111
This Breeze Airways deal was found by Cheapflights users on 9/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/42:52 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Sun 10/57:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/16$113
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/82:52 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Sun 10/127:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$117
This Breeze Airways deal was found by Cheapflights users on 9/17. 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.
Fri 10/172:34 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Mon 10/207:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/17$123
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/22:15 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Mon 10/67:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/17$126
This Breeze Airways deal was found by Cheapflights users on 9/15. 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.
Fri 10/32:34 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Mon 10/67:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$128
This Breeze Airways deal was found by Cheapflights users on 9/15. 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.
Mon 10/62:34 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Thu 10/97:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$133
This Breeze Airways deal was found by Cheapflights users on 9/15. 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.
Thu 10/92:15 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Sat 10/117:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$138
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/162:15 pmJAX - ORF
Nonstop1h 38mBreeze Airways
Mon 10/207:05 amORF - JAX
Nonstop1h 53mBreeze Airways
Deal found 9/15$141

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 September 17, 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

Sat 10/25

2:52 pm-4:30 pm

Nonstop1h 38m

Norfolk

Wed 10/29

7:05 am-8:58 am

Nonstop1h 53m

$98

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Thu 12/11

2:25 pm-4:03 pm

Nonstop1h 38m

Norfolk

Mon 12/15

7:05 am-8:58 am

Nonstop1h 53m

$98

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 10/1

2:52 pm-4:30 pm

Nonstop1h 38m

Norfolk

Fri 10/3

7:05 am-8:58 am

Nonstop1h 53m

$103

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Fri 10/31

2:34 pm-4:12 pm

Nonstop1h 38m

Norfolk

Fri 11/7

7:05 am-8:58 am

Nonstop1h 53m

$111

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Sat 10/4

2:52 pm-4:30 pm

Nonstop1h 38m

Norfolk

Sun 10/5

7:05 am-8:58 am

Nonstop1h 53m

$118

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 10/15

2:52 pm-4:30 pm

Nonstop1h 38m

Norfolk

Wed 10/22

7:05 am-8:58 am

Nonstop1h 53m

$118

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Fri 10/17

2:34 pm-4:12 pm

Nonstop1h 38m

Norfolk

Mon 10/20

7:05 am-8:58 am

Nonstop1h 53m

$123

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 10/22

2:52 pm-4:30 pm

Nonstop1h 38m

Norfolk

Fri 10/24

7:05 am-8:58 am

Nonstop1h 53m

$128

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Mon 10/6

2:34 pm-4:12 pm

Nonstop1h 38m

Norfolk

Thu 10/9

7:05 am-8:58 am

Nonstop1h 53m

$133

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Fri 10/3

2:34 pm-4:12 pm

Nonstop1h 38m

Norfolk

Sun 10/5

7:05 am-8:58 am

Nonstop1h 53m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
1
2
3

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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Jacksonville to Chesapeake, you should look to book at least 56 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 September 17, 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 September 14, 2025.

Travelers seeking maximum savings on their Jacksonville to Chesapeake flight should consider departing on Sunday afternoons 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 September 17, 2025.
See what other customers who have flown with Southwest, Breeze Airways, and Delta 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
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Breeze Airways
8.0
Very good
207 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Allegiant Air
7.2
Good
699 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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. 5 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.

  • How long is the flight from Jacksonville to Chesapeake?

    Breeze Airways can get you from Jacksonville to Chesapeake in just under 1h 38m. Your travel time will be generally consistent. Jacksonville and Chesapeake are separated by a distance of 543 mi. Generally, flights for this route are nonstop.

  • What are the cheapest flights from Jacksonville to Chesapeake?

    The cheapest flight price from Jacksonville to Chesapeake is $64. On average you can expect to pay $162. The most popular route, (Jacksonville - Norfolk), can usually be booked for $98.

  • 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 5 airlines flying from Jacksonville to Chesapeake

Discover the top 5 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$45Average$81FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$73Average$160FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$155Average$331FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$349FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$283Average$396FlexibilityNo cancel feeOn-time63%

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