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Chesapeake

$59+ Cheap flights from Kentucky 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — RIC
Mar 26 — Apr 21
Thu 3/26
Thu 4/2
1 adult, Economy
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Cheap flight deals from Kentucky to Chesapeake

Cheapest flights from Kentucky to Chesapeake
Explore the most affordable flight options available from Kentucky to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/23. 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 5/147:43 pm
CVG
-
ORF
1 stop14h 41m
Frontier
Sun 5/1711:19 am
ORF
-
CVG
1 stop7h 17m
Frontier
Deal found 2/23$153
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 5/27:46 pm
CVG
-
ORF
1 stop14h 51m
Multiple Airlines
Sat 5/98:27 pm
ORF
-
CVG
1 stop25h 27m
Multiple Airlines
Deal found 2/22$158
This Orbitz deal was found by Cheapflights users on 2/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
CVG
-
ORF
1 stop11h 49m
Frontier
Sat 5/911:19 am
ORF
-
CVG
1 stop7h 17m
Frontier
Deal found 2/23$160
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.
Wed 5/1310:00 am
CVG
-
ORF
1 stop11h 45m
Multiple Airlines
Sun 5/1711:19 am
ORF
-
CVG
1 stop7h 17m
Multiple Airlines
Deal found 2/20$164
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/247:44 am
BNA
-
ORF
1 stop11h 02m
Spirit Airlines
Tue 3/318:41 pm
ORF
-
BNA
1 stop17h 48m
Spirit Airlines
Deal found 2/22$173
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.
Wed 5/135:20 pm
CVG
-
ORF
2 stops17h 04m
Frontier
Sun 5/1711:19 am
ORF
-
CVG
1 stop7h 17m
Frontier
Deal found 2/20$175
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/108:30 am
BNA
-
ORF
1 stop8h 56m
Multiple Airlines
Sat 3/1410:31 pm
ORF
-
BNA
1 stop13h 55m
Multiple Airlines
Deal found 2/22$179
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.
Wed 4/12:27 pm
BNA
-
ORF
1 stop28h 19m
Spirit Airlines
Mon 4/68:41 pm
ORF
-
BNA
1 stop17h 48m
Spirit Airlines
Deal found 2/20$180
This Kiwi.com deal was found by Cheapflights users on 2/23. 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 5/87:59 pm
CVG
-
ORF
2 stops14h 25m
Frontier
Mon 5/1111:19 am
ORF
-
CVG
1 stop7h 17m
Frontier
Deal found 2/23$183
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 3/77:46 pm
CVG
-
ORF
1 stop13h 54m
Multiple Airlines
Wed 3/117:31 pm
ORF
-
CVG
1 stop16h 35m
Multiple Airlines
Deal found 2/21$184
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.
Sat 5/27:46 pm
CVG
-
ORF
1 stop14h 51m
Multiple Airlines
Sun 5/108:27 pm
ORF
-
CVG
1 stop25h 09m
Multiple Airlines
Deal found 2/20$188
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 4/17:44 am
BNA
-
ORF
1 stop11h 02m
Multiple Airlines
Sat 4/188:27 pm
ORF
-
BNA
1 stop16h 29m
Multiple Airlines
Deal found 2/21$193

Find flight deals from Kentucky to Chesapeake

Keep the following information in mind while searching for Kentucky to Chesapeake flight deals. Data was last updated February 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$153
(Kiwi.com)

One-way from

$59
(Trip.com)

Popular in

January

Cheapest in

November

Average price

$531
Provider with most accurate pricing for Louisville Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Norfolk flights.
Search Deals
From Kentucky to Chesapeake
Search Deals
One-way flight from Kentucky to Chesapeake
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 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 Kentucky 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 24, 2026.
Use the filters below to find and compare flights from Kentucky to Chesapeake that are best for you.

Fly from

Kentucky

Fly to

Chesapeake

Route

Depart

Return

Price

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Thu 5/14

7:43 pm-10:24 am

1 stop14h 41m

Norfolk

Sun 5/17

11:19 am-6:36 pm

1 stop7h 17m

$153

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Thu 3/5

1:07 pm-10:15 am

1 stop21h 08m

Norfolk

Fri 3/6

7:31 pm-6:35 pm

1 stop23h 04m

$231

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Wed 5/6

2:33 pm-7:10 pm

1 stop4h 37m

Norfolk

Sun 5/10

6:02 am-10:24 am

1 stop4h 22m

$241

BlountvilleNorfolk

TRI - ORF

TRIORF

Blountville Tri Cities TN/VA

Fri 5/8

7:41 pm-12:48 am

1 stop5h 07m

Norfolk

Sat 5/9

5:20 am-9:31 am

1 stop4h 11m

$249

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Thu 5/14

7:43 pm-10:24 am

1 stop14h 41m

Norfolk

Sun 5/17

8:27 pm-3:52 pm

2 stops19h 25m

$257

BlountvilleNorfolk

TRI - ORF

TRIORF

Blountville Tri Cities TN/VA

Tue 3/10

7:09 pm-10:58 pm

1 stop3h 49m

Norfolk

Sat 3/14

7:57 pm-11:47 pm

1 stop3h 50m

$259

LexingtonNorfolk

LEX - ORF

LEXORF

Lexington Blue Grass

Tue 3/10

4:22 pm-10:08 pm

1 stop5h 46m

Norfolk

Sat 3/14

9:13 am-2:33 pm

1 stop5h 20m

$259

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Mon 3/23

2:06 pm-9:47 pm

1 stop7h 41m

Norfolk

Mon 3/30

11:33 am-2:10 pm

2 stops26h 37m

$259

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Wed 4/22

6:05 am-10:29 am

1 stop4h 24m

Norfolk

Sun 4/26

6:00 am-11:50 am

1 stop5h 50m

$261

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Wed 4/22

2:45 pm-9:55 pm

2 stops6h 10m

Norfolk

Tue 4/28

6:50 am-2:30 pm

2 stops8h 40m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Chesapeake

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

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

Currently, August is the cheapest month in which you can book a flight from Kentucky to Chesapeake (average of $158). Flying from Kentucky to Chesapeake in December is currently the most expensive (average of $295). 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.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kentucky to Chesapeake?

    Frontier, Delta, and American Airlines can get you from Kentucky to Chesapeake in just under 4h 37m. Your travel time can differ by up to 10h 04m. Airlines will cover a distance of 484 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $96. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Kentucky to Chesapeake for a low price.

  • What are the most popular routes from Kentucky to Chesapeake?

    When deciding which route to take from Kentucky to Chesapeake consider Nashville Intl - Norfolk, Cincinnati Cinci./N. Kentucky - Norfolk or Louisville Intl - Norfolk as they are the most popular.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Kentucky to Chesapeake (average of $158). Flying from Kentucky to Chesapeake in December is currently the most expensive (average of $295). 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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Alternative routes for Kentucky to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Chesapeake

Discover the top 4 airlines that operate flights from Kentucky 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 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$318FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$369FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$278Average$348FlexibilityNo cancel feeOn-time69%

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