$71+ Cheap flights from Cleveland (CLE) 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Mar 16 — Mar 231
1 adult, Economy
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Find cheap flights from Cleveland 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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Cheapest flights from Cleveland to ChesapeakeExplore the most affordable flight options available from Cleveland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.
Explore the most affordable flight options available from Cleveland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/198:46 pm
CLE
- ORF
1 stop13h 51m
Frontier
Mon 2/2311:39 am
ORF
- CLE
1 stop11h 32m
Frontier
Deal found 2/11![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/18:45 pm
CLE
- ORF
1 stop13h 57m
Multiple Airlines
Tue 3/316:45 am
ORF
- CLE
1 stop18h 28m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/37:04 pm
CLE
- ORF
1 stop23h 22m
Multiple Airlines
Tue 3/107:31 pm
ORF
- CLE
1 stop18h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/282:40 pm
CLE
- ORF
1 stop19h 57m
Multiple Airlines
Tue 3/178:41 pm
ORF
- CLE
1 stop26h 47m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 5/1510:00 pm
CLE
- ORF
1 stop19h 49m
Multiple Airlines
Tue 5/196:05 am
ORF
- CLE
1 stop8h 03m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$156
This Frontier deal was found by Cheapflights users on 2/12. 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.
Fri 4/245:30 am
CLE
- ORF
1 stop12h 19m
Frontier
Mon 4/276:43 pm
ORF
- CLE
1 stop6h 27m
Frontier
Deal found 2/12![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/1610:00 pm
CLE
- ORF
1 stop23h 47m
Multiple Airlines
Tue 3/246:45 am
ORF
- CLE
1 stop11h 34m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/117:30 am
CLE
- ORF
1 stop10h 56m
Multiple Airlines
Thu 3/1211:50 am
ORF
- CLE
1 stop11h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/65:35 pm
CLE
- ORF
1 stop25h 54m
Multiple Airlines
Tue 5/126:05 am
ORF
- CLE
1 stop8h 03m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/88:25 pm
CLE
- ORF
2 stops21h 24m
Multiple Airlines
Wed 5/136:05 am
ORF
- CLE
1 stop8h 03m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$167
Best flights from Cleveland to ChesapeakeDiscover carefully curated flight deals from Cleveland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
Discover carefully curated flight deals from Cleveland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 5/1510:00 pm
CLE
- ORF
1 stop19h 49m
Multiple Airlines
Tue 5/196:05 am
ORF
- CLE
1 stop8h 03m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$156
This Expedia deal was found by Cheapflights users on 2/10. 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.
Thu 4/235:30 am
CLE
- ORF
1 stop12h 19m
Frontier
Fri 4/246:43 pm
ORF
- CLE
1 stop6h 27m
Frontier
Deal found 2/10![Frontier logo]()
$160
This Travelocity deal was found by Cheapflights users on 2/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:51 am
CLE
- ORF
1 stop8h 58m
Frontier
Sun 5/176:43 pm
ORF
- CLE
1 stop6h 27m
Frontier
Deal found 2/10![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/38:46 pm
CLE
- ORF
2 stops21h 40m
Multiple Airlines
Tue 3/107:31 pm
ORF
- CLE
1 stop18h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$161
This Frontier deal was found by Cheapflights users on 2/10. 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.
Fri 5/85:30 am
CLE
- ORF
1 stop12h 19m
Frontier
Mon 5/116:43 pm
ORF
- CLE
1 stop6h 27m
Frontier
Deal found 2/10![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/810:00 pm
CLE
- ORF
1 stop19h 49m
Multiple Airlines
Wed 5/136:05 am
ORF
- CLE
1 stop8h 03m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$172
This Frontier deal was found by Cheapflights users on 2/13. 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.
Fri 4/245:30 am
CLE
- ORF
1 stop12h 19m
Frontier
Mon 4/2711:19 am
ORF
- CLE
1 stop11h 55m
Frontier
Deal found 2/13![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 5/710:00 pm
CLE
- ORF
1 stop19h 49m
Multiple Airlines
Tue 5/126:05 am
ORF
- CLE
1 stop8h 03m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$173
This Frontier deal was found by Cheapflights users on 2/10. 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.
Fri 5/155:30 am
CLE
- ORF
1 stop12h 19m
Frontier
Mon 5/1811:19 am
ORF
- CLE
1 stop11h 55m
Frontier
Deal found 2/10![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 4/204:31 pm
CLE
- ORF
1 stop6h 27m
Multiple Airlines
Wed 4/226:05 am
ORF
- CLE
1 stop17h 35m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/18:45 pm
CLE
- ORF
1 stop13h 57m
Frontier
Sun 3/1511:25 am
ORF
- CLE
1 stop23h 15m
Frontier
Deal found 2/11![Frontier logo]()
$181
This Travelocity deal was found by Cheapflights users on 2/13. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:00 pm
CLE
- ORF
1 stop19h 49m
Frontier
Thu 4/236:43 pm
ORF
- CLE
1 stop6h 27m
Frontier
Deal found 2/13![Frontier logo]()
$181
Last-minute flights from Cleveland to ChesapeakeDiscover last-minute flight deals from Cleveland to Chesapeake. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chesapeake. Data last updated February 14, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/198:46 pm
CLE
- ORF
1 stop13h 51m
Frontier
Mon 2/2311:39 am
ORF
- CLE
1 stop11h 32m
Frontier
Deal found 2/11![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/271:26 pm
CLE
- ORF
2 stops32h 24m
Multiple Airlines
Tue 3/178:41 pm
ORF
- CLE
1 stop26h 47m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/282:40 pm
CLE
- ORF
1 stop19h 57m
Multiple Airlines
Tue 3/178:41 pm
ORF
- CLE
1 stop26h 47m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$152
This Frontier deal was found by Cheapflights users on 2/10. 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 2/2810:16 am
CLE
- ORF
1 stop5h 36m
Frontier
Mon 3/211:39 am
ORF
- CLE
1 stop11h 32m
Frontier
Deal found 2/10![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/282:40 pm
CLE
- ORF
1 stop19h 57m
Frontier
Sun 3/1511:25 am
ORF
- CLE
1 stop23h 15m
Frontier
Deal found 2/11![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/18:45 pm
CLE
- ORF
1 stop13h 57m
Multiple Airlines
Tue 3/316:45 am
ORF
- CLE
1 stop18h 28m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/37:04 pm
CLE
- ORF
1 stop23h 22m
Multiple Airlines
Tue 3/107:31 pm
ORF
- CLE
1 stop18h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/117:30 am
CLE
- ORF
1 stop10h 56m
Multiple Airlines
Thu 3/1211:50 am
ORF
- CLE
1 stop11h 21m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/1610:00 pm
CLE
- ORF
1 stop23h 47m
Multiple Airlines
Tue 3/246:45 am
ORF
- CLE
1 stop11h 34m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/186:31 pm
CLE
- ORF
1 stop25h 15m
Multiple Airlines
Mon 3/2312:33 pm
ORF
- CLE
1 stop23h 48m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 3/247:14 pm
CLE
- ORF
1 stop26h 33m
Multiple Airlines
Tue 3/316:45 am
ORF
- CLE
1 stop18h 28m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$180
One-way flights from Cleveland to ChesapeakeSearch for one-way flight options from Cleveland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
Search for one-way flight options from Cleveland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/84:31 pm
CLE
- ORF
1 stop25h 18m
Frontier
Deal found 2/11![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/37:04 pm
CLE
- ORF
1 stop23h 22m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$80
This Expedia deal was found by Cheapflights users on 2/10. 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.
Thu 4/2310:00 pm
CLE
- ORF
1 stop19h 49m
Frontier
Deal found 2/10![Frontier logo]()
$86
This Trip.com deal was found by Cheapflights users on 2/11. 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.
Mon 3/29:06 am
CLE
- ORF
1 stop26h 59m
Frontier
Deal found 2/11![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/38:46 pm
CLE
- ORF
2 stops21h 40m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/88:25 pm
CLE
- ORF
2 stops21h 24m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/65:35 pm
CLE
- ORF
1 stop25h 54m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$104
This Expedia deal was found by Cheapflights users on 2/11. 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 3/2510:00 pm
CLE
- ORF
1 stop19h 48m
Frontier
Deal found 2/11![Frontier logo]()
$107
This Travelocity deal was found by Cheapflights users on 2/13. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:57 pm
CLE
- ORF
1 stop16h 38m
Frontier
Deal found 2/13![Frontier logo]()
$108
This Trip.com deal was found by Cheapflights users on 2/12. 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.
Sun 3/1510:00 pm
CLE
- ORF
1 stop16h 31m
Frontier
Deal found 2/12![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 2/236:29 pm
CLE
- ORF
1 stop17h 36m
Frontier
Deal found 2/12![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/63:20 pm
CLE
- ORF
1 stop7h 38m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$117
Find flight deals from Cleveland to Chesapeake
Keep the following information in mind while searching for Cleveland to Chesapeake flight deals. Data was last updated February 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $144 (Kiwi.com) |
One-way from | $71 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $327 |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland 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 14, 2026.
Use the filters below to find and compare flights from Cleveland to Chesapeake that are best for you.
Fly from
Cleveland
Fly to
Chesapeake
Route
Depart
Return
Price
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 5/15
10:00 pm-5:49 pm
1 stop19h 49m
Norfolk
Tue 5/19
6:05 am-2:08 pm
1 stop8h 03m
$156
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 4/23
5:30 am-5:49 pm
1 stop12h 19m
Norfolk
Fri 4/24
6:43 pm-1:10 am
1 stop6h 27m
$160
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 5/15
8:51 am-5:49 pm
1 stop8h 58m
Norfolk
Sun 5/17
6:43 pm-1:10 am
1 stop6h 27m
$160
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 5/8
5:30 am-5:49 pm
1 stop12h 19m
Norfolk
Mon 5/11
6:43 pm-1:10 am
1 stop6h 27m
$160
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 4/24
5:30 am-5:49 pm
1 stop12h 19m
Norfolk
Mon 4/27
11:19 am-11:14 pm
1 stop11h 55m
$160
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Tue 3/3
8:46 pm-6:26 pm
2 stops21h 40m
Norfolk
Tue 3/10
7:31 pm-2:27 pm
1 stop18h 56m
$161
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 5/8
10:00 pm-5:49 pm
1 stop19h 49m
Norfolk
Wed 5/13
6:05 am-2:08 pm
1 stop8h 03m
$172
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 5/7
10:00 pm-5:49 pm
1 stop19h 49m
Norfolk
Tue 5/12
6:05 am-2:08 pm
1 stop8h 03m
$173
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 5/15
5:30 am-5:49 pm
1 stop12h 19m
Norfolk
Mon 5/18
11:19 am-11:14 pm
1 stop11h 55m
$181
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Sun 3/1
8:45 pm-10:42 am
1 stop13h 57m
Norfolk
Sun 3/15
11:25 am-10:40 am
1 stop23h 15m
$181
Showing 1-10 of 23 results
Best time to book a flight from Cleveland to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Cleveland with our price prediction graph.
CLE-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 Cleveland to Chesapeake
CLE-C6E
CLE-ORF
How far ahead should I book a flight from Cleveland to Chesapeake?
Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Chesapeake. Price data was last updated on February 6, 2026.
The price you pay for your flight from Cleveland to Chesapeake may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Cleveland to Chesapeake?
Currently, August is the cheapest month in which you can book a flight from Cleveland to Chesapeake (average of $56). Flying from Cleveland to Chesapeake in July is currently the most expensive (average of $118). 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.
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 February 14, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Cleveland to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Cleveland to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Cleveland to Chesapeake
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Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
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Cleveland and Chesapeake flights
Browse other Cleveland and Chesapeake flight options. Last updated on February 14, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on February 14, 2026.
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Cleveland to Chesapeake flights
Consider these flights traveling from Cleveland to Chesapeake.
Top 5 airlines flying from Cleveland to Chesapeake
Discover the top 5 airlines that operate flights from Cleveland 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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$280 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$304 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$353 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$312 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$198 | Average$317 | FlexibilityNo cancel fee | On-time63% |