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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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — RIC
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
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 December 28, 2025.

This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:23 pmTYS - ORF
1 stop4h 18mUnited Airlines
Fri 1/210:46 amORF - TYS
1 stop4h 02mUnited Airlines
Deal found 12/27$297
This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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.
Tue 12/305:45 amBNA - ORF
1 stop12h 00mSpirit Airlines
Tue 1/63:01 pmORF - BNA
1 stop5h 42mSpirit Airlines
Deal found 12/27$331
This United Airlines deal was found by Cheapflights users on 12/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:23 pmTYS - ORF
1 stop4h 18mUnited Airlines
Tue 12/302:47 pmORF - TYS
1 stop5h 04mUnited Airlines
Deal found 12/26$352
This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:22 pmBNA - ORF
1 stop4h 35mUnited Airlines
Tue 1/66:30 amORF - BNA
2 stops10h 24mUnited Airlines
Deal found 12/27$356
This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:44 pmBNA - ORF
1 stop7h 38mUnited Airlines
Thu 1/16:20 amORF - BNA
1 stop4h 50mUnited Airlines
Deal found 12/27$375
This Delta deal was found by Cheapflights users on 12/26. 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.
Tue 12/306:14 pmBNA - ORF
1 stop3h 42mDelta
Fri 1/23:45 pmORF - BNA
1 stop6h 10mDelta
Deal found 12/26$380
This American Airlines deal was found by Cheapflights users on 12/25. 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.
Fri 12/267:05 amBNA - ORF
1 stop6h 43mAmerican Airlines
Mon 12/298:19 pmORF - BNA
1 stop4h 19mAmerican Airlines
Deal found 12/25$409
This United Airlines deal was found by Cheapflights users on 12/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:45 amTYS - ORF
1 stop4h 10mUnited Airlines
Thu 1/17:55 pmORF - TYS
1 stop4h 04mUnited Airlines
Deal found 12/26$429
This American Airlines deal was found by Cheapflights users on 12/26. 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.
Sat 12/275:42 amTYS - ORF
1 stop4h 05mAmerican Airlines
Fri 1/210:07 amORF - TYS
1 stop5h 40mAmerican Airlines
Deal found 12/26$432
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/316:30 amCVG - ORF
1 stop7h 36mMultiple Airlines
Sun 1/43:01 pmORF - CVG
2 stops27h 13mMultiple Airlines
Deal found 12/26$467
This Southwest deal was found by Cheapflights users on 12/26. 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 12/306:40 amBNA - ORF
1 stop5h 10mSouthwest
Fri 1/26:10 amORF - BNA
2 stops5h 50mSouthwest
Deal found 12/26$469
This American Airlines deal was found by Cheapflights users on 12/26. 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.
Wed 12/3111:17 amCVG - ORF
1 stop8h 58mAmerican Airlines
Fri 1/26:00 amORF - CVG
1 stop8h 48mAmerican Airlines
Deal found 12/26$529

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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$134
(Kiwi.com)

One-way from

$59
(Trip.com)

Popular in

January

Cheapest in

November

Average price

$571
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 ($136 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 28, 2025.
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

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Thu 1/29

8:40 am-6:38 pm

1 stop8h 58m

Norfolk

Sun 2/1

7:33 pm-7:25 am

1 stop12h 52m

$134

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Sun 1/11

2:20 pm-6:38 pm

1 stop28h 18m

Norfolk

Thu 1/15

7:33 pm-2:00 pm

1 stop18h 27m

$157

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Thu 1/8

2:12 pm-6:38 pm

1 stop27h 26m

Norfolk

Sun 1/11

7:33 pm-7:25 am

1 stop12h 52m

$187

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Thu 1/15

8:00 am-6:38 pm

1 stop10h 38m

Norfolk

Fri 1/16

7:33 pm-2:38 pm

1 stop19h 05m

$191

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Fri 1/9

8:40 am-6:38 pm

1 stop8h 58m

Norfolk

Mon 1/12

7:33 pm-7:43 pm

1 stop25h 10m

$192

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Mon 1/12

8:40 am-6:38 pm

1 stop8h 58m

Norfolk

Thu 1/15

6:45 am-7:43 pm

2 stops13h 58m

$205

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Thu 3/19

10:45 am-7:45 am

1 stop21h 00m

Norfolk

Wed 3/25

8:29 pm-10:00 pm

1 stop25h 31m

$222

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Sat 1/10

3:11 pm-6:38 pm

1 stop27h 27m

Norfolk

Wed 1/14

8:00 am-2:17 pm

2 stops30h 17m

$228

LouisvilleNorfolk

SDF - ORF

SDFORF

Louisville Intl

Tue 2/24

3:33 pm-6:26 pm

1 stop26h 53m

Norfolk

Tue 3/10

7:31 pm-12:21 pm

2 stops16h 50m

$229

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Fri 1/9

8:30 am-6:38 pm

1 stop10h 08m

Norfolk

Sun 1/11

2:29 pm-5:28 pm

1 stop26h 59m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

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 March is currently the most expensive (average of $298). 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?

    Spirit Airlines, Delta, and American Airlines can get you from Kentucky to Chesapeake in just under 3h 44m. Your travel time can differ by up to 5h 14m. Airlines will cover a distance of 440 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 Cincinnati Cinci./N. Kentucky - Norfolk, Nashville Intl - Norfolk or Knoxville McGhee Tyson - 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 March is currently the most expensive (average of $298). 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$406FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$324FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$398FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$278Average$348FlexibilityNo cancel feeOn-time69%

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