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Chesapeake

$54+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — RIC
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chesapeake are usually found in May or September, booked 57 days in advance, depart on a Sunday or Thursday and return on a Wednesday

Cheap 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 February 21, 2026.

This Booking.com deal was found by Cheapflights users on 2/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:32 am
JAX
-
ORF
Nonstop1h 42m
Breeze Airways
Sat 5/168:00 am
ORF
-
JAX
Nonstop1h 52m
Breeze Airways
Deal found 2/18$114
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:27 pm
JAX
-
ORF
Nonstop1h 39m
Breeze Airways
Mon 4/275:51 pm
ORF
-
JAX
Nonstop1h 56m
Breeze Airways
Deal found 2/19$119
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:25 pm
JAX
-
ORF
Nonstop1h 39m
Breeze Airways
Sun 4/261:09 pm
ORF
-
JAX
Nonstop1h 56m
Breeze Airways
Deal found 2/19$128
This Mytrip deal was found by Cheapflights users on 2/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:27 pm
JAX
-
ORF
Nonstop1h 39m
Breeze Airways
Sun 4/261:09 pm
ORF
-
JAX
Nonstop1h 56m
Breeze Airways
Deal found 2/17$129
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/278:27 pm
JAX
-
ORF
Nonstop1h 39m
Multiple Airlines
Mon 3/3011:33 am
ORF
-
JAX
1 stop8h 00m
Multiple Airlines
Deal found 2/20$133
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Wed 3/188:18 pm
JAX
-
ORF
1 stop13h 57m
Frontier
Mon 3/2312:33 pm
ORF
-
JAX
1 stop4h 35m
Frontier
Deal found 2/17$136
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Wed 4/18:18 pm
JAX
-
ORF
1 stop14h 18m
Frontier
Mon 4/611:33 am
ORF
-
JAX
1 stop8h 00m
Frontier
Deal found 2/17$138
This Priceline deal was found by Cheapflights users on 2/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:27 pm
JAX
-
ORF
Nonstop1h 39m
Multiple Airlines
Mon 4/2711:27 am
ORF
-
JAX
1 stop6h 37m
Multiple Airlines
Deal found 2/19$141
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/278:27 pm
JAX
-
ORF
Nonstop1h 39m
Breeze Airways
Mon 3/305:51 pm
ORF
-
JAX
Nonstop1h 56m
Breeze Airways
Deal found 2/20$142
This Booking.com deal was found by Cheapflights users on 2/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:32 am
JAX
-
ORF
Nonstop1h 42m
Breeze Airways
Wed 6/108:00 am
ORF
-
JAX
Nonstop1h 52m
Breeze Airways
Deal found 2/16$143

Find flight deals from Jacksonville to Chesapeake

Keep the following information in mind while searching for Jacksonville to Chesapeake flight deals. Data was last updated February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$114
(Booking.com)

One-way from

$54
(Booking.com)

Popular in

December

Cheapest in

May

Average price

$223
Provider with most accurate pricing for Jacksonville-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville-Norfolk flights.
Search Deals
From Jacksonville to Chesapeake
Search Deals
One-way flight from Jacksonville to Chesapeake
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 21, 2026.
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

Wed 5/13

10:32 am-12:14 pm

Nonstop1h 42m

Norfolk

Sat 5/16

8:00 am-9:52 am

Nonstop1h 52m

$114

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Fri 3/27

8:27 pm-10:06 pm

Nonstop1h 39m

Norfolk

Mon 3/30

11:33 am-7:33 pm

1 stop8h 00m

$133

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 3/18

8:18 pm-10:15 am

1 stop13h 57m

Norfolk

Mon 3/23

12:33 pm-5:08 pm

1 stop4h 35m

$136

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 4/1

8:18 pm-10:36 am

1 stop14h 18m

Norfolk

Mon 4/6

11:33 am-7:33 pm

1 stop8h 00m

$138

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Fri 3/6

8:27 pm-10:06 pm

Nonstop1h 39m

Norfolk

Fri 3/13

5:51 pm-7:47 pm

Nonstop1h 56m

$189

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Mon 3/2

8:27 pm-10:06 pm

Nonstop1h 39m

Norfolk

Mon 3/9

5:51 pm-7:47 pm

Nonstop1h 56m

$192

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Thu 3/26

8:25 pm-10:04 pm

Nonstop1h 39m

Norfolk

Sun 3/29

1:09 pm-3:05 pm

Nonstop1h 56m

$193

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 3/25

8:18 pm-10:15 am

1 stop13h 57m

Norfolk

Sun 3/29

11:19 am-5:29 pm

1 stop6h 10m

$195

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Thu 4/16

8:25 pm-10:04 pm

Nonstop1h 39m

Norfolk

Fri 4/17

11:07 am-6:35 pm

1 stop7h 28m

$199

JacksonvilleNorfolk

JAX - ORF

JAXORF

Jacksonville

Wed 3/4

7:53 pm-10:51 am

1 stop14h 58m

Norfolk

Sat 3/7

10:31 pm-4:08 pm

1 stop17h 37m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 20 results
1
2

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 February 20, 2026.

To ensure you get the cheapest price possible for a flight from Jacksonville to Chesapeake, you should look to book at least 57 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, May is the cheapest month in which you can book a flight from Jacksonville to Chesapeake (average of $43). Flying from Jacksonville to Chesapeake in December is currently the most expensive (average of $126). 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 February 21, 2026.

It’s typically best to fly out from Jacksonville to Chesapeake in the morning. Doing so could potentially save you 25% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 February 17, 2026.

Travelers seeking maximum savings on their Jacksonville to Chesapeake flight should consider departing on Tuesday evenings when fares are most often at their lowest. Tuesday afternoons 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 February 21, 2026.
See what other customers who have flown with Breeze Airways, Southwest, 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.
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Food

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
271 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Food

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,298 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Food

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,232 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Food

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Allegiant Air
7.3
Good
711 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Food

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,337 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Food

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 and Frontier can get you from Jacksonville to Chesapeake in just under 1h 42m. Your travel time can differ by up to 12h 15m. Jacksonville and Chesapeake are separated by a distance of 543 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $45 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 Southwest, with prices starting from $49 and $88, respectively.

  • What are the cheapest flights from Jacksonville to Chesapeake?

    The cheapest flight price from Jacksonville to Chesapeake is $183. On average you can expect to pay $258. The most popular route, (Jacksonville - Norfolk), can usually be booked for $119.

  • 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, May is the cheapest month in which you can book a flight from Jacksonville to Chesapeake (average of $43). Flying from Jacksonville to Chesapeake in December is currently the most expensive (average of $126). 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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$42Average$80FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$79Average$166FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$113Average$339FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$327FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$278Average$424FlexibilityNo cancel feeOn-time63%

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