$48+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — RIC
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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Find cheap flights from Jacksonville to Chesapeake with Cheapflights
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Jacksonville to Chesapeake are usually found in September or October, booked 76 days in advance, depart on a Thursday or Saturday and return on a Wednesday
Cheap flight deals from Jacksonville to Chesapeake
Cheapest
Best
Last-minute
One-way
Cheapest flights from Jacksonville to ChesapeakeExplore 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 August 6, 2026.
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 August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/2310:36 am -
Nonstop1h 39m
Mon 9/288:03 pm -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/1110:39 pm -
Nonstop1h 39m
Mon 9/148:03 pm -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Tue 10/2710:20 am -
Nonstop1h 39m
Wed 10/281:48 pm -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/117:46 pm -
1 stop20h 04m
Mon 9/148:03 pm -
Nonstop1h 56m
Deal found 8/5![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/237:46 pm -
1 stop16h 43m
Mon 9/288:03 pm -
Nonstop1h 56m
Deal found 8/5![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/24:44 pm -
Nonstop1h 42m
Sun 9/61:18 pm -
Nonstop1h 52m
Deal found 8/5![Breeze Airways logo]()
$142
This Breeze Airways deal was found by Cheapflights users on 8/5. 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 11/56:25 pm -
Nonstop1h 39m
Sun 11/83:49 pm -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/910:39 pm -
Nonstop1h 39m
Sun 10/113:49 pm -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:50 pm -
Nonstop1h 42m
Sun 9/131:18 pm -
1 stop5h 43m
Deal found 8/4![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/27:05 pm -
1 stop17h 20m
Sun 9/61:20 pm -
1 stop4h 50m
Deal found 8/5![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/203:31 pm -
Nonstop1h 42m
Sat 8/227:06 pm -
Nonstop1h 52m
Deal found 8/5![Breeze Airways logo]()
$157
This Breeze Airways deal was found by Cheapflights users on 8/4. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:31 pm -
Nonstop1h 42m
Mon 8/247:05 am -
Nonstop1h 52m
Deal found 8/4![Breeze Airways logo]()
$158
Best flights from Jacksonville to ChesapeakeDiscover carefully curated flight deals from Jacksonville to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
Discover carefully curated flight deals from Jacksonville to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/3. 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 8/203:31 pm -
Nonstop1h 42m
Mon 8/247:05 am -
Nonstop1h 52m
Deal found 8/3![Breeze Airways logo]()
$173
This Delta deal was found by Cheapflights users on 8/1. 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 9/176:00 am -
1 stop3h 47m
Mon 9/217:19 pm -
1 stop4h 39m
Deal found 8/1![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 8/256:45 am -
2 stops7h 45m
Thu 8/2710:10 am -
1 stop5h 05m
Deal found 8/3![Southwest logo]()
$204
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 10/97:00 pm -
1 stop5h 45m
Mon 10/127:33 pm -
1 stop4h 23m
Deal found 8/4![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:25 pm -
2 stops8h 30m
Mon 8/316:00 am -
2 stops7h 20m
Deal found 8/4![Southwest logo]()
$209
This Breeze Airways deal was found by Cheapflights users on 8/2. 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 8/149:37 am -
Nonstop1h 42m
Mon 8/177:05 am -
Nonstop1h 52m
Deal found 8/2![Breeze Airways logo]()
$248
This Southwest deal was found by Cheapflights users on 8/1. 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.
Thu 10/221:30 pm -
2 stops10h 05m
Mon 10/266:25 am -
1 stop3h 55m
Deal found 8/1![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 8/5. 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 9/186:59 pm -
1 stop5h 36m
Sun 9/207:24 pm -
1 stop4h 43m
Deal found 8/5![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 8/277:50 am -
1 stop10h 05m
Fri 8/286:25 am -
2 stops8h 50m
Deal found 8/3![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:30 pm -
2 stops10h 05m
Sun 10/256:20 am -
1 stop4h 00m
Deal found 8/4![Southwest logo]()
$279
Last-minute flights from Jacksonville to ChesapeakeDiscover last-minute flight deals from Jacksonville to Chesapeake. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chesapeake. Data last updated August 6, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:44 pm -
Nonstop1h 42m
Wed 8/267:06 pm -
Nonstop1h 52m
Deal found 8/4![Breeze Airways logo]()
$157
This Breeze Airways deal was found by Cheapflights users on 8/4. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:31 pm -
Nonstop1h 42m
Mon 8/247:05 am -
Nonstop1h 52m
Deal found 8/4![Breeze Airways logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/24:44 pm -
Nonstop1h 42m
Sun 9/61:18 pm -
Nonstop1h 52m
Deal found 8/5![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/27:05 pm -
1 stop17h 20m
Sun 9/61:20 pm -
1 stop4h 50m
Deal found 8/5![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:50 pm -
Nonstop1h 42m
Sun 9/131:18 pm -
1 stop5h 43m
Deal found 8/4![Multiple Airlines logo]()
$155
This Breeze Airways deal was found by Cheapflights users on 8/6. 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 9/106:25 pm -
Nonstop1h 39m
Mon 9/288:03 pm -
Nonstop1h 56m
Deal found 8/6![Breeze Airways logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/1110:39 pm -
Nonstop1h 39m
Mon 9/148:03 pm -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/117:46 pm -
1 stop20h 04m
Mon 9/148:03 pm -
Nonstop1h 56m
Deal found 8/5![Multiple Airlines logo]()
$131
This Breeze Airways deal was found by Cheapflights users on 8/6. 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 9/176:25 pm -
Nonstop1h 39m
Mon 9/218:03 pm -
Nonstop1h 56m
Deal found 8/6![Breeze Airways logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/1910:36 am -
Nonstop1h 39m
Sat 9/268:00 am -
Nonstop1h 56m
Deal found 8/5![Breeze Airways logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/1910:36 am -
Nonstop1h 39m
Sat 9/264:45 pm -
1 stop26h 16m
Deal found 8/5![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/237:46 pm -
1 stop16h 43m
Mon 9/288:03 pm -
Nonstop1h 56m
Deal found 8/5![Multiple Airlines logo]()
$137
One-way flights from Jacksonville to ChesapeakeSearch for one-way flight options from Jacksonville to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
Search for one-way flight options from Jacksonville to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Mon 9/2110:39 pm -
Nonstop1h 39m
Deal found 8/5![Breeze Airways logo]()
$48
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sun 9/136:25 pm -
Nonstop1h 39m
Deal found 8/3![Breeze Airways logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:39 pm -
Nonstop1h 39m
Deal found 8/4![Breeze Airways logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 9/106:25 pm -
Nonstop1h 39m
Deal found 8/5![Breeze Airways logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/294:44 pm -
Nonstop1h 42m
Deal found 8/1![Breeze Airways logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/287:05 pm -
1 stop17h 20m
Deal found 8/3![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Mon 9/217:46 pm -
1 stop16h 43m
Deal found 8/5![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/289:37 am -
Nonstop1h 42m
Deal found 8/3![Breeze Airways logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/27:46 pm -
1 stop20h 04m
Deal found 8/5![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/297:05 pm -
1 stop17h 20m
Deal found 8/1![Frontier logo]()
$80
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $97 (Kiwi.com) |
One-way from | $48 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $258 |
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 August 6, 2026.
Use the filters below to find and compare flights from Jacksonville to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Thu 8/20
3:31 pm-5:13 pm
Nonstop1h 42m
Norfolk
Mon 8/24
7:05 am-8:57 am
Nonstop1h 52m
$173
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Thu 9/17
6:00 am-9:47 am
1 stop3h 47m
Norfolk
Mon 9/21
7:19 pm-11:58 pm
1 stop4h 39m
$199
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Fri 10/9
7:00 pm-12:45 am
1 stop5h 45m
Norfolk
Mon 10/12
7:33 pm-11:56 pm
1 stop4h 23m
$199
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Tue 8/25
6:45 am-2:30 pm
2 stops7h 45m
Norfolk
Thu 8/27
10:10 am-3:15 pm
1 stop5h 05m
$204
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Sat 8/29
12:25 pm-8:55 pm
2 stops8h 30m
Norfolk
Mon 8/31
6:00 am-1:20 pm
2 stops7h 20m
$209
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Fri 8/14
9:37 am-11:19 am
Nonstop1h 42m
Norfolk
Mon 8/17
7:05 am-8:57 am
Nonstop1h 52m
$248
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Thu 10/22
1:30 pm-11:35 pm
2 stops10h 05m
Norfolk
Mon 10/26
6:25 am-10:20 am
1 stop3h 55m
$269
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Thu 8/27
7:50 am-5:55 pm
1 stop10h 05m
Norfolk
Fri 8/28
6:25 am-3:15 pm
2 stops8h 50m
$275
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Fri 9/18
6:59 pm-12:35 am
1 stop5h 36m
Norfolk
Sun 9/20
7:24 pm-12:07 am
1 stop4h 43m
$278
JacksonvilleNorfolk
JAX Jacksonville - ORF Norfolk
JAXORF
Jacksonville
Fri 10/23
1:30 pm-11:35 pm
2 stops10h 05m
Norfolk
Sun 10/25
6:20 am-10:20 am
1 stop4h 00m
$279
Showing 1-10 of 21 resultsSorted by cheapest first
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.
JAX-ORF
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
JAX-C6E
JAX-ORF
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 August 6, 2026.
It’s typically best to fly out from Jacksonville to Chesapeake in the morning. Doing so could potentially save you 31% on the flight price compared to flying in the evening, which is usually more expensive.
How much does it cost to fly round-trip from Jacksonville to Chesapeake?
Airfare is below average for this route at the moment.
Jacksonville to Chesapeake flights typically cost between $188 and $318 in September.The cheapest round-trip price found within the last 5 days was $97 on Breeze Airways (Sep 19-Sep 26).
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 August 1, 2026.
Travelers seeking maximum savings on their Jacksonville to Chesapeake flight should consider departing on Monday afternoons 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 August 6, 2026.
See what other customers who have flown with Breeze Airways,Southwest, andDelta 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.
Comfort
8.2
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
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Jacksonville and Chesapeake flights
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$218 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$432 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$218 | Average$391 | FlexibilityNo cancel fee | On-time71% |