HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$62+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — RIC
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kentucky 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.

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 April 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/2312:46 pm
CVG
-
ORF
1 stop22h 25m
Frontier
Mon 5/2512:06 pm
ORF
-
CVG
1 stop6h 23m
Frontier
Deal found 4/22$126
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Wed 6/1712:54 pm
CVG
-
ORF
1 stop22h 32m
Frontier
Wed 6/2412:21 pm
ORF
-
CVG
1 stop22h 53m
Frontier
Deal found 4/22$127
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/1512:46 pm
CVG
-
ORF
1 stop22h 09m
Frontier
Mon 5/189:12 pm
ORF
-
CVG
1 stop15h 55m
Frontier
Deal found 4/23$128
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Fri 5/2212:46 pm
CVG
-
ORF
1 stop22h 29m
Frontier
Mon 5/2512:06 pm
ORF
-
CVG
1 stop6h 23m
Frontier
Deal found 4/26$139
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/1512:46 pm
CVG
-
ORF
1 stop22h 09m
Frontier
Tue 5/1912:06 pm
ORF
-
CVG
2 stops25h 11m
Frontier
Deal found 4/23$153
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 6/2012:52 pm
CVG
-
ORF
1 stop22h 34m
Frontier
Sat 6/2712:06 pm
ORF
-
CVG
1 stop23h 08m
Frontier
Deal found 4/22$154
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mon 5/113:38 pm
CVG
-
ORF
2 stops43h 33m
Multiple Airlines
Mon 5/2512:06 pm
ORF
-
CVG
1 stop6h 23m
Multiple Airlines
Deal found 4/23$168
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Wed 5/137:00 am
CVG
-
ORF
2 stops28h 11m
Frontier
Wed 5/2712:06 pm
ORF
-
CVG
1 stop22h 58m
Frontier
Deal found 4/23$180
This Frontier deal was found by Cheapflights users on 4/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:37 pm
CVG
-
ORF
1 stop26h 17m
Frontier
Mon 5/119:12 pm
ORF
-
CVG
1 stop26h 17m
Frontier
Deal found 4/25$181
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/2112:12 pm
CVG
-
ORF
1 stop22h 59m
Frontier
Tue 5/2612:06 pm
ORF
-
CVG
1 stop23h 35m
Frontier
Deal found 4/23$182
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:05 pm
BNA
-
ORF
1 stop4h 44m
Spirit Airlines
Sun 5/106:34 pm
ORF
-
BNA
1 stop5h 40m
Spirit Airlines
Deal found 4/22$186
This Cheapflightsfares deal was found by Cheapflights users on 4/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:00 am
BNA
-
ORF
1 stop10h 57m
Spirit Airlines
Mon 6/86:42 pm
ORF
-
BNA
1 stop5h 36m
Spirit Airlines
Deal found 4/25$194

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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$126
(Kiwi.com)

One-way from

$62
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$400
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. 31% potential increase in price ($179 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 27, 2026.
Use the filters below to find and compare flights from Kentucky to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Wed 5/27

5:14 pm-9:47 pm

1 stop3h 33m

Norfolk

Sat 5/30

4:39 pm-8:06 pm

1 stop4h 27m

$223

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Tue 5/26

9:30 am-11:11 am

2 stops25h 41m

Norfolk

Fri 5/29

7:05 am-10:01 pm

1 stop14h 56m

$256

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Wed 6/17

8:10 am-11:55 am

1 stop3h 45m

Norfolk

Wed 6/24

3:40 pm-8:20 pm

1 stop4h 40m

$265

CincinnatiNorfolk

CVG - ORF

CVGORF

Cincinnati Cinci./N. Kentucky

Tue 5/12

7:50 pm-11:50 pm

1 stop4h 00m

Norfolk

Thu 5/14

6:00 am-1:07 pm

1 stop7h 07m

$279

NashvilleNorfolk

BNA - ORF

BNAORF

Nashville Intl

Mon 5/11

6:30 pm-11:50 pm

1 stop4h 20m

Norfolk

Wed 5/13

6:15 am-12:26 pm

2 stops7h 11m

$279

LexingtonNorfolk

LEX - ORF

LEXORF

Lexington Blue Grass

Wed 9/30

4:10 pm-8:58 pm

1 stop4h 48m

Norfolk

Tue 10/6

5:16 am-10:33 am

1 stop5h 17m

$287

LexingtonNorfolk

LEX - ORF

LEXORF

Lexington Blue Grass

Sat 10/10

7:10 am-12:47 pm

1 stop5h 37m

Norfolk

Sat 10/17

5:50 am-10:20 am

1 stop4h 30m

$287

LexingtonNorfolk

LEX - ORF

LEXORF

Lexington Blue Grass

Sat 5/30

5:52 pm-11:20 pm

1 stop5h 28m

Norfolk

Wed 6/3

10:08 am-2:46 pm

1 stop4h 38m

$287

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Thu 5/28

11:56 am-5:21 pm

1 stop5h 25m

Norfolk

Sun 5/31

5:20 am-9:34 am

1 stop4h 14m

$297

KnoxvilleNorfolk

TYS - ORF

TYSORF

Knoxville McGhee Tyson

Tue 8/11

10:05 am-3:31 pm

1 stop5h 26m

Norfolk

Thu 8/13

9:40 am-3:07 pm

1 stop5h 27m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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

How much does it cost to fly round-trip from Kentucky to Chesapeake?

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?

    Delta, Southwest, and United Airlines can get you from Kentucky to Chesapeake in just under 3h 33m. Your travel time can differ by up to 27m. Airlines will cover a distance of 584 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 Lexington Blue Grass - 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kentucky to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to Dulles Intl flights
Los Angeles to Reagan-National flights
Los Angeles to Dulles Intl flights
Seattle to Dulles Intl flights
Seattle to Reagan-National flights
LaGuardia to Raleigh flights
Dallas/Fort Worth to Reagan-National flights
Atlanta to Dulles Intl flights
San Francisco to Dulles Intl flights
Atlanta to Reagan-National flights
San Francisco to Reagan-National flights
Newark to Raleigh flights
O'Hare Intl to Dulles Intl flights
Boston to Raleigh flights
John F Kennedy Intl to Raleigh flights
Hobby to Dulles Intl flights
O'Hare Intl to Reagan-National flights
Boston to Dulles Intl flights
Detroit to Dulles Intl flights
Tampa to Dulles Intl flights
Orlando to Dulles Intl flights
Denver to Dulles Intl flights
Hobby to Reagan-National flights
Dallas/Fort Worth to Raleigh flights
Boston to Reagan-National flights
George Bush Intcntl to Dulles Intl flights
Miami to Dulles Intl flights
Seattle to Raleigh flights
Los Angeles to Raleigh flights
George Bush Intcntl to Reagan-National flights
Detroit to Reagan-National flights
Minneapolis to Dulles Intl flights
Orlando to Reagan-National flights
Sky Harbor Intl to Dulles Intl flights
Denver to Raleigh flights
O'Hare Intl to Raleigh flights
Tampa to Reagan-National flights
San Diego to Dulles Intl flights
Austin to Reagan-National flights
Charlotte to Dulles Intl flights
Miami to Reagan-National flights
Denver to Reagan-National flights
Minneapolis to Reagan-National flights
Portland to Dulles Intl flights
Austin to Dulles Intl flights
Midway to Dulles Intl flights
Fort Lauderdale to Dulles Intl flights
Boston to Richmond flights
San Francisco to Raleigh flights
Sky Harbor Intl to Reagan-National flights

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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$372FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$381FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$278Average$348FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.