$60+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Mar 29 — Apr 51
1 adult, Economy
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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 27, 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 27, 2026.
This Lucky2Go deal was found by Cheapflights users on 2/24. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:46 pm
CLE
- ORF
1 stop18h 46m
Frontier
Sun 4/1911:27 am
ORF
- CLE
1 stop22h 12m
Frontier
Deal found 2/24![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Thu 4/238:55 pm
CLE
- ORF
1 stop13h 22m
Frontier
Mon 4/2711:27 am
ORF
- CLE
1 stop20h 17m
Frontier
Deal found 2/26![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Tue 4/214:46 pm
CLE
- ORF
1 stop23h 05m
Multiple Airlines
Mon 4/2711:27 am
ORF
- CLE
1 stop20h 17m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 5/68:25 pm
CLE
- ORF
2 stops37h 59m
Frontier
Mon 5/1111:19 am
ORF
- CLE
1 stop11h 55m
Frontier
Deal found 2/24![Frontier logo]()
$153
This Frontier deal was found by Cheapflights users on 2/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:30 am
CLE
- ORF
1 stop11h 37m
Frontier
Fri 5/16:00 pm
ORF
- CLE
1 stop5h 59m
Frontier
Deal found 2/26![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 4/95:30 am
CLE
- ORF
1 stop5h 06m
Frontier
Mon 4/1311:33 am
ORF
- CLE
1 stop20h 11m
Frontier
Deal found 2/24![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Mon 4/208:50 am
CLE
- ORF
1 stop8h 17m
Frontier
Thu 4/3011:27 am
ORF
- CLE
1 stop22h 16m
Frontier
Deal found 2/26![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:01 pm
CLE
- ORF
1 stop16h 23m
Frontier
Mon 5/186:43 pm
ORF
- CLE
1 stop6h 27m
Frontier
Deal found 2/23![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Thu 4/238:55 pm
CLE
- ORF
1 stop13h 22m
Multiple Airlines
Tue 4/288:05 am
ORF
- CLE
1 stop23h 34m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 4/224:46 pm
CLE
- ORF
2 stops17h 46m
Frontier
Mon 4/2711:27 am
ORF
- CLE
1 stop20h 17m
Frontier
Deal found 2/26![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 5/66:01 pm
CLE
- ORF
1 stop16h 23m
Multiple Airlines
Wed 5/137:00 am
ORF
- CLE
1 stop15h 08m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$173
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 27, 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 27, 2026.
This Delta deal was found by Cheapflights users on 2/26. 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 4/215:00 pm
CLE
- ORF
1 stop5h 36m
Delta
Tue 4/286:00 am
ORF
- CLE
1 stop4h 00m
Delta
Deal found 2/26![Delta logo]()
$243
This Southwest deal was found by Cheapflights users on 2/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:40 am
CLE
- ORF
1 stop3h 45m
Southwest
Sun 4/126:05 pm
ORF
- CLE
1 stop6h 00m
Southwest
Deal found 2/25![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Thu 5/217:26 pm
CLE
- ORF
1 stop5h 15m
United Airlines
Fri 5/226:05 am
ORF
- CLE
1 stop3h 36m
United Airlines
Deal found 2/26![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 2/26. 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 5/1910:51 am
CLE
- ORF
1 stop5h 11m
Delta
Mon 5/256:00 am
ORF
- CLE
1 stop3h 20m
Delta
Deal found 2/26![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 2/24. 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 5/62:45 pm
CLE
- ORF
2 stops7h 10m
Southwest
Mon 5/112:30 pm
ORF
- CLE
2 stops7h 45m
Southwest
Deal found 2/24![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 2/26. 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.
Thu 4/97:09 am
CLE
- ORF
1 stop4h 41m
Delta
Sun 4/125:45 am
ORF
- CLE
1 stop3h 59m
Delta
Deal found 2/26![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:45 pm
CLE
- ORF
2 stops7h 10m
Southwest
Mon 5/186:05 am
ORF
- CLE
2 stops9h 00m
Southwest
Deal found 2/23![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 2/26. 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 3/276:00 am
CLE
- ORF
1 stop3h 44m
United Airlines
Sun 3/296:08 am
ORF
- CLE
1 stop3h 32m
United Airlines
Deal found 2/26![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 2/24. 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 5/28:50 am
CLE
- ORF
2 stops9h 20m
Southwest
Sun 5/31:00 pm
ORF
- CLE
2 stops8h 00m
Southwest
Deal found 2/24![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 2/26. 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.
Sat 5/2310:51 am
CLE
- ORF
1 stop5h 11m
Delta
Mon 5/256:00 am
ORF
- CLE
1 stop3h 20m
Delta
Deal found 2/26![Delta logo]()
$367
This United Airlines deal was found by Cheapflights users on 2/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:00 am
CLE
- ORF
1 stop3h 44m
United Airlines
Sun 3/156:10 am
ORF
- CLE
1 stop3h 40m
United Airlines
Deal found 2/25![United Airlines logo]()
$431
Last-minute flights from Cleveland to ChesapeakeDiscover last-minute flight deals from Cleveland to Chesapeake. Data last updated February 27, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Chesapeake. Data last updated February 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/97:04 pm
CLE
- ORF
1 stop23h 22m
Multiple Airlines
Fri 3/1312:42 pm
ORF
- CLE
1 stop19h 00m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/114:40 pm
CLE
- ORF
1 stop27h 06m
Multiple Airlines
Mon 3/168:41 pm
ORF
- CLE
1 stop20h 32m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/124:02 pm
CLE
- ORF
1 stop19h 45m
Multiple Airlines
Mon 3/168:41 pm
ORF
- CLE
1 stop17h 56m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$239
This Expedia deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1310:00 pm
CLE
- ORF
1 stop16h 31m
Frontier
Sun 3/1512:42 pm
ORF
- CLE
1 stop12h 31m
Frontier
Deal found 2/23![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Tue 3/177:30 am
CLE
- ORF
1 stop12h 16m
Multiple Airlines
Thu 3/1911:50 am
ORF
- CLE
1 stop11h 21m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Tue 3/176:31 pm
CLE
- ORF
1 stop25h 15m
Multiple Airlines
Tue 3/248:41 pm
ORF
- CLE
1 stop26h 47m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/196:01 pm
CLE
- ORF
1 stop16h 41m
Frontier
Sun 3/223:50 pm
ORF
- CLE
1 stop18h 50m
Frontier
Deal found 2/24![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Thu 3/195:30 am
CLE
- ORF
2 stops14h 16m
Multiple Airlines
Sun 3/223:50 pm
ORF
- CLE
1 stop18h 50m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/266:01 pm
CLE
- ORF
1 stop16h 37m
Frontier
Mon 3/3011:33 am
ORF
- CLE
1 stop24h 33m
Frontier
Deal found 2/24![Frontier logo]()
$206
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 27, 2026.
Search for one-way flight options from Cleveland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated February 27, 2026.
This Trip.com deal was found by Cheapflights users on 2/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:45 am
CLE
- ORF
1 stop22h 39m
Frontier
Deal found 2/27![Frontier logo]()
$60
This Expedia deal was found by Cheapflights users on 2/24. 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.
Fri 5/810:00 pm
CLE
- ORF
1 stop19h 49m
Frontier
Deal found 2/24![Frontier logo]()
$86
This Frontier deal was found by Cheapflights users on 2/25. 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.
Thu 5/75:30 am
CLE
- ORF
1 stop12h 19m
Frontier
Deal found 2/25![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:04 pm
CLE
- ORF
1 stop24h 42m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Mon 3/236:45 pm
CLE
- ORF
1 stop25h 01m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$111
This Priceline deal was found by Cheapflights users on 2/24. 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.
Sun 3/295:30 am
CLE
- ORF
1 stop4h 54m
Frontier
Deal found 2/24![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 2/24. 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 5/65:50 am
CLE
- ORF
1 stop6h 05m
Southwest
Deal found 2/24![Southwest logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1310:00 pm
CLE
- ORF
1 stop16h 31m
Frontier
Deal found 2/25![Frontier logo]()
$120
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $124 (Lucky2Go) |
One-way from | $60 (Trip.com) |
Popular in | January |
Cheapest in | September |
Average price | $330 |
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 27, 2026.
Use the filters below to find and compare flights from Cleveland to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Tue 4/21
5:00 pm-10:36 pm
1 stop5h 36m
Norfolk
Tue 4/28
6:00 am-10:00 am
1 stop4h 00m
$243
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Tue 5/19
10:51 am-4:02 pm
1 stop5h 11m
Norfolk
Mon 5/25
6:00 am-9:20 am
1 stop3h 20m
$305
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 4/9
5:40 am-9:25 am
1 stop3h 45m
Norfolk
Sun 4/12
6:05 pm-12:05 am
1 stop6h 00m
$309
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 4/9
7:09 am-11:50 am
1 stop4h 41m
Norfolk
Sun 4/12
5:45 am-9:44 am
1 stop3h 59m
$319
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Wed 5/6
2:45 pm-9:55 pm
2 stops7h 10m
Norfolk
Mon 5/11
2:30 pm-10:15 pm
2 stops7h 45m
$331
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 5/15
3:45 pm-10:55 pm
2 stops7h 10m
Norfolk
Mon 5/18
6:05 am-3:05 pm
2 stops9h 00m
$347
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Sat 5/2
8:50 am-6:10 pm
2 stops9h 20m
Norfolk
Sun 5/3
1:00 pm-9:00 pm
2 stops8h 00m
$362
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Sat 5/23
10:51 am-4:02 pm
1 stop5h 11m
Norfolk
Mon 5/25
6:00 am-9:20 am
1 stop3h 20m
$367
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Thu 5/21
7:26 pm-12:41 am
1 stop5h 15m
Norfolk
Fri 5/22
6:05 am-9:41 am
1 stop3h 36m
$387
ClevelandNorfolk
CLE - ORF
CLEORF
Cleveland Hopkins Intl
Fri 3/27
6:00 am-9:44 am
1 stop3h 44m
Norfolk
Sun 3/29
6:08 am-9:40 am
1 stop3h 32m
$407
Showing 1-10 of 21 resultsSorted by cheapest first
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 20, 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 29 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 27, 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
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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Cleveland and Chesapeake flights
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$280 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$338 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$317 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$198 | Average$317 | FlexibilityNo cancel fee | On-time63% |