$75+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — RIC
Sep 17 — Sep 241
Round-trip
1 adult, Economy
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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
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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
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Cheapest flights from Kentucky to ChesapeakeExplore 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 August 18, 2026.
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 August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/512:26 pm -
1 stop23h 59m
Sat 9/124:45 pm -
1 stop18h 53m
Deal found 8/15![Frontier logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/2312:43 pm -
1 stop23h 46m
Sun 9/271:18 pm -
1 stop22h 20m
Deal found 8/17![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1212:43 pm -
1 stop23h 46m
Sat 9/194:45 pm -
1 stop18h 53m
Deal found 8/13![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/2512:43 pm -
1 stop27h 07m
Sat 10/34:45 pm -
1 stop18h 53m
Deal found 8/13![Frontier logo]()
$159
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:43 am -
1 stop8h 05m
Mon 9/287:43 pm -
1 stop22h 02m
Deal found 8/13![Frontier logo]()
$160
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:52 am -
1 stop6h 56m
Tue 9/227:43 pm -
1 stop22h 02m
Deal found 8/13![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/1612:43 pm -
1 stop26h 12m
Sun 10/251:19 pm -
1 stop22h 19m
Deal found 8/14![Frontier logo]()
$165
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:05 pm -
1 stop22h 06m
Tue 9/157:43 pm -
1 stop14h 05m
Deal found 8/13![Frontier logo]()
$165
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:43 pm -
1 stop23h 51m
Sat 10/243:50 pm -
1 stop16h 00m
Deal found 8/16![Frontier logo]()
$172
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:56 pm -
1 stop21h 52m
Mon 9/147:43 pm -
1 stop27h 58m
Deal found 8/16![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 8/3012:26 pm -
1 stop23h 59m
Tue 9/151:18 pm -
1 stop22h 20m
Deal found 8/15![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:43 pm -
2 stops11h 35m
Sun 10/41:18 pm -
1 stop22h 20m
Deal found 8/16![Multiple Airlines logo]()
$191
Best flights from Kentucky to ChesapeakeDiscover carefully curated flight deals from Kentucky to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2026.
Discover carefully curated flight deals from Kentucky to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2026.
This Trip.com deal was found by Cheapflights users on 8/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:56 pm -
1 stop21h 52m
Mon 9/147:43 pm -
1 stop27h 58m
Deal found 8/15![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Sun 8/308:40 pm -
1 stop10h 51m
Sun 9/201:18 pm -
1 stop22h 20m
Deal found 8/17![Multiple Airlines logo]()
$198
This Delta deal was found by Cheapflights users on 8/13. 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 11/311:50 am -
1 stop4h 30m
Tue 11/107:00 am -
1 stop4h 29m
Deal found 8/13![Delta logo]()
$203
This Southwest deal was found by Cheapflights users on 8/13. 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 10/311:35 am -
2 stops6h 35m
Mon 10/55:45 am -
1 stop6h 45m
Deal found 8/13![Southwest logo]()
$258
This JetBlue deal was found by Cheapflights users on 8/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:27 pm -
1 stop5h 33m
Sun 11/16:00 am -
1 stop8h 32m
Deal found 8/16![JetBlue logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/245:45 am -
1 stop3h 57m
Sat 10/316:15 am -
2 stops9h 37m
Deal found 8/14![United Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Thu 9/107:21 pm -
1 stop3h 20m
Sun 9/138:09 pm -
1 stop3h 47m
Deal found 8/15![American Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:44 pm -
1 stop4h 32m
Fri 10/235:05 pm -
1 stop5h 30m
Deal found 8/17![Delta logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Sun 8/309:23 pm -
2 stops39h 02m
Sun 9/201:18 pm -
1 stop22h 20m
Deal found 8/17![Frontier logo]()
$264
This Delta deal was found by Cheapflights users on 8/15. 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 9/255:24 pm -
1 stop5h 02m
Mon 9/287:19 pm -
1 stop5h 04m
Deal found 8/15![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 8/13. 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 9/36:00 am -
1 stop6h 20m
Sat 9/52:50 pm -
Nonstop1h 55m
Deal found 8/13![Southwest logo]()
$272
This JetBlue deal was found by Cheapflights users on 8/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:25 pm -
1 stop7h 16m
Tue 9/297:25 am -
1 stop7h 03m
Deal found 8/15![JetBlue logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/36:00 am -
1 stop3h 34m
Sun 9/65:02 pm -
1 stop6h 57m
Deal found 8/13![United Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/46:00 am -
1 stop3h 50m
Tue 9/87:23 pm -
1 stop3h 46m
Deal found 8/14![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/148:00 am -
2 stops28h 29m
Thu 9/177:43 pm -
1 stop16h 58m
Deal found 8/14![Multiple Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:45 am -
2 stops8h 30m
Fri 10/236:05 pm -
1 stop6h 00m
Deal found 8/17![Southwest logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:18 pm -
1 stop3h 23m
Sun 9/275:00 am -
1 stop6h 09m
Deal found 8/17![American Airlines logo]()
$310
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:10 am -
1 stop5h 03m
Thu 9/175:02 pm -
1 stop7h 03m
Deal found 8/16![United Airlines logo]()
$313
This JetBlue deal was found by Cheapflights users on 8/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:25 pm -
1 stop7h 16m
Mon 10/57:25 am -
1 stop7h 04m
Deal found 8/17![JetBlue logo]()
$316
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 am -
1 stop3h 55m
Mon 10/127:33 pm -
1 stop4h 42m
Deal found 8/16![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 8/15. 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.
Wed 10/145:00 pm -
1 stop4h 05m
Mon 10/195:50 pm -
Nonstop2h 00m
Deal found 8/15![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Sun 10/49:04 am -
1 stop6h 12m
Mon 10/126:15 am -
1 stop4h 03m
Deal found 8/13![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 8/13. 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 11/121:49 pm -
1 stop6h 33m
Fri 12/411:00 am -
1 stop3h 55m
Deal found 8/13![Delta logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am -
1 stop3h 50m
Sun 9/61:45 pm -
1 stop3h 55m
Deal found 8/18![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/15. 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.
Mon 10/129:55 pm -
1 stop10h 25m
Thu 10/155:50 pm -
Nonstop2h 00m
Deal found 8/15![Southwest logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/296:00 am -
1 stop3h 39m
Wed 9/24:00 pm -
1 stop5h 07m
Deal found 8/14![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:59 pm -
1 stop4h 36m
Sun 9/276:00 am -
1 stop3h 44m
Deal found 8/17![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Thu 10/297:35 pm -
1 stop4h 09m
Sat 10/3112:26 pm -
1 stop8h 28m
Deal found 8/15![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 8/15. 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 10/155:00 am -
1 stop5h 35m
Mon 10/196:05 pm -
2 stops7h 20m
Deal found 8/15![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:50 pm -
1 stop5h 43m
Thu 9/1010:52 am -
1 stop4h 06m
Deal found 8/17![Delta logo]()
$309
Last-minute flights from Kentucky to ChesapeakeDiscover last-minute flight deals from Kentucky to Chesapeake. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Chesapeake. Data last updated August 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 8/3012:26 pm -
1 stop23h 59m
Tue 9/151:18 pm -
1 stop22h 20m
Deal found 8/15![Frontier logo]()
$188
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:05 pm -
1 stop22h 06m
Tue 9/157:43 pm -
1 stop14h 05m
Deal found 8/13![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/512:26 pm -
1 stop23h 59m
Sat 9/124:45 pm -
1 stop18h 53m
Deal found 8/15![Frontier logo]()
$149
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:56 pm -
1 stop21h 52m
Mon 9/147:43 pm -
1 stop27h 58m
Deal found 8/16![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1012:43 pm -
2 stops10h 13m
Sun 9/131:18 pm -
1 stop22h 20m
Deal found 8/13![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:43 pm -
1 stop27h 07m
Tue 9/151:18 pm -
1 stop22h 20m
Deal found 8/18![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:43 pm -
2 stops11h 35m
Tue 9/151:18 pm -
1 stop22h 20m
Deal found 8/18![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1212:43 pm -
1 stop23h 46m
Sat 9/194:45 pm -
1 stop18h 53m
Deal found 8/13![Frontier logo]()
$151
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:52 am -
1 stop6h 56m
Tue 9/227:43 pm -
1 stop22h 02m
Deal found 8/13![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/2312:43 pm -
1 stop23h 46m
Sun 9/271:18 pm -
1 stop22h 20m
Deal found 8/17![Frontier logo]()
$150
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:43 am -
1 stop8h 05m
Mon 9/287:43 pm -
1 stop22h 02m
Deal found 8/13![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/2512:43 pm -
1 stop27h 07m
Sat 10/34:45 pm -
1 stop18h 53m
Deal found 8/13![Frontier logo]()
$159
One-way flights from Kentucky to ChesapeakeSearch for one-way flight options from Kentucky to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
Search for one-way flight options from Kentucky to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:43 pm -
1 stop26h 12m
Deal found 8/18![Frontier logo]()
$75
This Frontier deal was found by Cheapflights users on 8/13. 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.
Wed 9/99:43 am -
1 stop8h 05m
Deal found 8/13![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 11/167:37 pm -
1 stop20h 38m
Deal found 8/14![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 11/97:37 pm -
1 stop20h 38m
Deal found 8/13![Frontier logo]()
$82
This Expedia deal was found by Cheapflights users on 8/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:56 pm -
1 stop21h 52m
Deal found 8/16![Frontier logo]()
$85
This Jetabroad deal was found by Cheapflights users on 8/13. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:05 pm -
1 stop22h 06m
Deal found 8/13![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/159:43 am -
1 stop8h 05m
Deal found 8/14![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/119:27 am -
1 stop8h 21m
Deal found 8/13![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/309:43 am -
2 stops25h 46m
Deal found 8/13![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/239:43 am -
2 stops25h 46m
Deal found 8/13![Frontier logo]()
$93
This Priceline deal was found by Cheapflights users on 8/13. 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.
Sat 9/129:43 am -
1 stop8h 05m
Deal found 8/13![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/165:40 pm -
2 stops17h 49m
Deal found 8/14![Frontier logo]()
$95
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 August 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $149 (Kiwi.com) |
One-way from | $75 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $526 |
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 August 18, 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
Cheapest round-trip
CincinnatiNorfolk
CVG Cincinnati Cinci./N. Kentucky - ORF Norfolk
CVGORF
Cincinnati Cinci./N. Kentucky
Thu 9/10
8:56 pm-6:48 pm
1 stop21h 52m
Norfolk
Mon 9/14
7:43 pm-11:41 pm
1 stop27h 58m
$177
CincinnatiNorfolk
CVG Cincinnati Cinci./N. Kentucky - ORF Norfolk
CVGORF
Cincinnati Cinci./N. Kentucky
Sun 8/30
8:40 pm-7:31 am
1 stop10h 51m
Norfolk
Sun 9/20
1:18 pm-11:38 am
1 stop22h 20m
$198
KnoxvilleNorfolk
TYS Knoxville McGhee Tyson - ORF Norfolk
TYSORF
Knoxville McGhee Tyson
Tue 11/3
11:50 am-4:20 pm
1 stop4h 30m
Norfolk
Tue 11/10
7:00 am-11:29 am
1 stop4h 29m
$203
CincinnatiNorfolk
CVG Cincinnati Cinci./N. Kentucky - ORF Norfolk
CVGORF
Cincinnati Cinci./N. Kentucky
Sat 10/17
1:44 pm-6:16 pm
1 stop4h 32m
Norfolk
Fri 10/23
5:05 pm-10:35 pm
1 stop5h 30m
$244
CincinnatiNorfolk
CVG Cincinnati Cinci./N. Kentucky - ORF Norfolk
CVGORF
Cincinnati Cinci./N. Kentucky
Fri 9/25
5:24 pm-10:26 pm
1 stop5h 02m
Norfolk
Mon 9/28
7:19 pm-12:23 am
1 stop5h 04m
$244
NashvilleNorfolk
BNA Nashville Intl - ORF Norfolk
BNAORF
Nashville Intl
Sat 10/3
11:35 am-7:10 pm
2 stops6h 35m
Norfolk
Mon 10/5
5:45 am-11:30 am
1 stop6h 45m
$258
CincinnatiNorfolk
CVG Cincinnati Cinci./N. Kentucky - ORF Norfolk
CVGORF
Cincinnati Cinci./N. Kentucky
Sun 8/30
9:23 pm-12:25 pm
2 stops39h 02m
Norfolk
Sun 9/20
1:18 pm-11:38 am
1 stop22h 20m
$264
NashvilleNorfolk
BNA Nashville Intl - ORF Norfolk
BNAORF
Nashville Intl
Thu 9/3
6:00 am-1:20 pm
1 stop6h 20m
Norfolk
Sat 9/5
2:50 pm-3:45 pm
Nonstop1h 55m
$272
NashvilleNorfolk
BNA Nashville Intl - ORF Norfolk
BNAORF
Nashville Intl
Thu 10/29
2:27 pm-9:00 pm
1 stop5h 33m
Norfolk
Sun 11/1
6:00 am-1:32 pm
1 stop8h 32m
$277
NashvilleNorfolk
BNA Nashville Intl - ORF Norfolk
BNAORF
Nashville Intl
Fri 9/25
2:25 pm-10:41 pm
1 stop7h 16m
Norfolk
Tue 9/29
7:25 am-1:28 pm
1 stop7h 03m
$277
Showing 1-10 of 60 resultsSorted by cheapest first
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.
CVG-ORF
BNA-ORF
TYS-ORF
TRI-ORF
SDF-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 Kentucky to Chesapeake
USKY-C6E
CVG-ORF
BNA-ORF
TYS-ORF
TRI-ORF
How much does it cost to fly round-trip from Kentucky to Chesapeake?
Airfare is below average for this route at the moment.
Kentucky to Chesapeake flights typically cost between $313 and $632 in October.The cheapest round-trip price found within the last 5 days was $254 on Breeze Airways (Oct 30-Nov 1).
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.
Browse thousands of different options on Cheapflights for your next trip
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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.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Chesapeake by cabin class
Find flights from Kentucky to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Chesapeake flights
Browse other Kentucky and Chesapeake flight options. Last updated on August 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Chesapeake
Find the right flight back to Kentucky after your stay in Chesapeake
Kentucky to Chesapeake flights
Consider these flights traveling from Kentucky to Chesapeake.
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 August 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$390 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$400 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$419 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$366 | Average$456 | FlexibilityNo cancel fee | On-time63% |