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Chesapeake

$86+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
feb. 5 — feb. 121
jue. 2/5
jue. 2/12
1 adult, Economy
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Cheap flight deals from Cleveland to Chesapeake

Keep the following information in mind while searching for Cleveland to Chesapeake flight deals. Data was last updated enero 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$149
(Kiwi.com)

One-way from

$86
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$359
Provider with most accurate pricing for Cleveland Hopkins Intl-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Norfolk flights.
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From Cleveland Hopkins Intl to Chesapeake
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One-way flight from Cleveland Hopkins Intl to Chesapeake
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Highest demand for flights based on searches. 7% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Cleveland to Chesapeake

Cheapest flights from Cleveland to Chesapeake
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 enero 6, 2026.

This Expedia deal was found by Cheapflights users on 1/4. 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.
sáb. 1/2412:30 pmCLE - ORF
1 stop7h 45mFrontier
sáb. 1/319:10 pmORF - CLE
1 stop12h 46mFrontier
Deal found 1/4$144
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
mar. 2/36:00 pmCLE - ORF
1 stop23h 20mMultiple Airlines
mar. 2/107:33 pmORF - CLE
1 stop24h 10mMultiple Airlines
Deal found 1/5$149
This Frontier deal was found by Cheapflights users on 1/4. 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.
mié. 4/19:00 pmCLE - ORF
1 stop12h 23mFrontier
jue. 4/98:00 pmORF - CLE
1 stop11h 48mFrontier
Deal found 1/4$175
This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
sáb. 2/216:00 amCLE - ORF
1 stop15h 36mMultiple Airlines
mar. 2/247:31 pmORF - CLE
1 stop22h 38mMultiple Airlines
Deal found 1/4$177
This Delta deal was found by Cheapflights users on 1/6. 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.
jue. 3/54:25 pmCLE - ORF
1 stop5h 58mDelta
lun. 3/95:13 pmORF - CLE
1 stop7h 18mDelta
Deal found 1/6$181
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
vie. 2/207:30 amCLE - ORF
1 stop10h 56mMultiple Airlines
dom. 2/227:31 pmORF - CLE
1 stop22h 38mMultiple Airlines
Deal found 1/5$182
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
mar. 1/203:34 pmCLE - ORF
1 stop21h 52mMultiple Airlines
jue. 1/227:33 pmORF - CLE
1 stop22h 33mMultiple Airlines
Deal found 1/5$189
This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
jue. 2/197:30 amCLE - ORF
1 stop10h 56mMultiple Airlines
sáb. 2/217:00 amORF - CLE
1 stop11h 38mMultiple Airlines
Deal found 1/4$191
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
vie. 2/275:30 amCLE - ORF
1 stop17h 21mMultiple Airlines
lun. 3/27:31 pmORF - CLE
1 stop24h 12mMultiple Airlines
Deal found 1/5$195
This Delta deal was found by Cheapflights users on 1/5. 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.
sáb. 2/216:30 amCLE - ORF
1 stop5h 47mDelta
mar. 2/247:45 amORF - CLE
1 stop5h 37mDelta
Deal found 1/5$197

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 enero 6, 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

sáb. 1/24

12:30 pm-8:15 pm

1 stop7h 45m

Norfolk

sáb. 1/31

9:10 pm-9:56 am

1 stop12h 46m

$144

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

mar. 2/3

6:00 pm-5:20 pm

1 stop23h 20m

Norfolk

mar. 2/10

7:33 pm-7:43 pm

1 stop24h 10m

$149

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

sáb. 2/21

6:00 am-9:36 pm

1 stop15h 36m

Norfolk

mar. 2/24

7:31 pm-6:09 pm

1 stop22h 38m

$177

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

jue. 3/5

4:25 pm-10:23 pm

1 stop5h 58m

Norfolk

lun. 3/9

5:13 pm-12:31 am

1 stop7h 18m

$181

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

sáb. 2/21

6:30 am-12:17 pm

1 stop5h 47m

Norfolk

mar. 2/24

6:20 pm-12:30 am

1 stop6h 10m

$189

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

vie. 2/27

5:30 am-10:51 pm

1 stop17h 21m

Norfolk

lun. 3/2

7:31 pm-6:09 pm

1 stop22h 38m

$210

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

sáb. 1/17

7:55 pm-11:30 pm

1 stop3h 35m

Norfolk

mar. 1/20

6:13 am-9:51 am

1 stop3h 38m

$229

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

lun. 1/26

4:41 pm-11:27 pm

1 stop6h 46m

Norfolk

jue. 1/29

10:05 am-4:51 pm

1 stop6h 46m

$241

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

vie. 2/27

4:35 pm-11:00 pm

1 stop6h 25m

Norfolk

lun. 3/2

6:14 pm-12:30 am

1 stop6h 16m

$254

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

lun. 3/30

5:30 am-10:38 am

1 stop5h 08m

Norfolk

lun. 4/6

12:03 pm-5:13 pm

1 stop5h 10m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 20 results
1
2

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.
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

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 January 2, 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 April is currently the most expensive (average of $124). 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 enero 6, 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.
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,018 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,132 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,084 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,063 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • What airport do you fly from for flights from Cleveland to Chesapeake?

    Cleveland Hopkins Intl (CLE), located 10.1 mi from the city center, is the airport you fly out of when you book flights from Cleveland to Chesapeake. 5 airlines have flights from Hopkins Intl to Chesapeake on a regular basis. Booking flights from Cleveland Hopkins Intl to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • How long is the flight from Cleveland to Chesapeake?

    There are many flights that can get you from Cleveland to Chesapeake in 5h 58m. Fly via Frontier or Delta to get the fastest option. Airlines will cover a distance of 434 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Cleveland to Chesapeake one-way?

    One-way options have recently been found by users for as low as $55 on Frontier. Other airlines that offer cheap prices include American Airlines from $105 and Southwest from $108 one-way.

  • Can I find deals for flights from Cleveland to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Cleveland to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cleveland to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Chesapeake.

  • Can I find deals for business class flights from Cleveland to Chesapeake?

    Yes. Cheapflights offers flight deals from Cleveland to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from 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 April is currently the most expensive (average of $124). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 enero 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$290FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$353FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$308FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$315FlexibilityNo cancel feeOn-time63%
DeltaCheapest$214Average$303FlexibilityNo cancel feeOn-timeN/A

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