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Chesapeake

$72+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
oct. 17 — oct. 241
ven. 10/17
ven. 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chesapeake are usually found in April or May, booked 29 days in advance, depart on a Wednesday or Tuesday and return on a Monday

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 septembre 17, 2025.

Round-trip from

$156
(Booking.com)

One-way from

$72
(Priceline)

Popular in

January

Cheapest in

April

Average price

$291
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. 17% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septembre 17, 2025.

This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/12:00 pmCLE - ORF
1 stop26h 12mFrontier
dim. 10/55:47 pmORF - CLE
1 stop27h 08mFrontier
Deal found 9/16$156
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/265:30 amCLE - ORF
1 stop5h 54mFrontier
dim. 9/285:47 pmORF - CLE
1 stop19h 27mFrontier
Deal found 9/16$157
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/225:30 amCLE - ORF
1 stop5h 54mFrontier
jeu. 9/255:12 pmORF - CLE
1 stop27h 43mFrontier
Deal found 9/16$183
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 9/215:30 amCLE - ORF
1 stop5h 49mFrontier
jeu. 9/255:12 pmORF - CLE
1 stop23h 46mFrontier
Deal found 9/16$193
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/95:45 amCLE - ORF
1 stop9h 09mFrontier
dim. 10/124:14 pmORF - CLE
1 stop8h 33mFrontier
Deal found 9/14$208
This Delta deal was found by Cheapflights users on 9/17. 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.
mar. 10/146:00 amCLE - ORF
1 stop6h 31mDelta
mar. 10/214:23 pmORF - CLE
1 stop4h 18mDelta
Deal found 9/17$237
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/144:15 pmCLE - ORF
1 stop5h 35mSouthwest
mar. 10/212:55 pmORF - CLE
2 stops7h 50mSouthwest
Deal found 9/16$242
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
mar. 10/283:40 pmCLE - ORF
2 stops44h 36mMultiple Airlines
ven. 11/78:01 amORF - CLE
1 stop16h 37mMultiple Airlines
Deal found 9/17$246
This United Airlines deal was found by Cheapflights users on 9/16. 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.
ven. 11/147:10 pmCLE - ORF
1 stop4h 17mUnited Airlines
mer. 11/196:20 amORF - CLE
1 stop3h 15mUnited Airlines
Deal found 9/16$253
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
mer. 10/14:04 pmCLE - ORF
1 stop5h 59mMultiple Airlines
dim. 10/55:38 pmORF - CLE
2 stops19h 53mMultiple Airlines
Deal found 9/16$257
This Southwest deal was found by Cheapflights users on 9/17. 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.
mar. 10/286:35 amCLE - ORF
2 stops7h 45mSouthwest
ven. 11/74:15 pmORF - CLE
1 stop3h 10mSouthwest
Deal found 9/17$258
This Delta deal was found by Cheapflights users on 9/15. 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.
ven. 10/106:43 pmCLE - ORF
1 stop5h 37mDelta
lun. 10/137:45 pmORF - CLE
1 stop4h 51mDelta
Deal found 9/15$263

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 septembre 17, 2025.
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

ven. 10/3

5:30 am-11:24 am

1 stop5h 54m

Norfolk

dim. 10/5

5:47 pm-8:55 pm

1 stop27h 08m

$156

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

mar. 10/14

6:00 am-12:31 pm

1 stop6h 31m

Norfolk

mar. 10/21

4:23 pm-8:41 pm

1 stop4h 18m

$237

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

mar. 10/14

4:15 pm-9:50 pm

1 stop5h 35m

Norfolk

mar. 10/21

2:55 pm-10:45 pm

2 stops7h 50m

$242

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

mar. 10/28

3:40 pm-12:16 pm

2 stops44h 36m

Norfolk

ven. 11/7

8:01 am-12:38 am

1 stop16h 37m

$246

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

mar. 10/28

4:15 pm-9:50 pm

1 stop5h 35m

Norfolk

ven. 11/7

4:15 pm-7:25 pm

1 stop3h 10m

$253

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

mer. 10/1

4:04 pm-10:03 pm

1 stop5h 59m

Norfolk

dim. 10/5

5:38 pm-1:31 pm

2 stops19h 53m

$257

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

jeu. 10/9

5:45 am-11:25 am

1 stop5h 40m

Norfolk

lun. 10/13

8:35 pm-11:45 pm

1 stop3h 10m

$257

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ven. 10/10

6:43 pm-12:20 am

1 stop5h 37m

Norfolk

lun. 10/13

7:45 pm-12:36 am

1 stop4h 51m

$263

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ven. 10/17

11:00 am-3:10 pm

1 stop4h 10m

Norfolk

lun. 10/20

8:35 pm-11:45 pm

1 stop3h 10m

$263

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ven. 11/14

3:25 pm-11:35 pm

2 stops8h 10m

Norfolk

mer. 11/19

8:30 am-5:30 pm

2 stops9h 00m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 19 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 September 12, 2025.

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, January is the cheapest month in which you can book a flight from Cleveland to Chesapeake (average of $281). Flying from Cleveland to Chesapeake in March is currently the most expensive (average of $351). 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.

What is the cheapest time of day to fly from CLE to C6E?

Find hourly flight availability from Cleveland to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septembre 17, 2025.

When flying from Cleveland to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Cleveland to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Chesapeake. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Cleveland to Chesapeake flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 septembre 17, 2025.
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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 35m. Fly via Frontier, Delta, or Southwest to get the fastest option. Airlines will cover a distance of 434 mi. This flight may include one or multiple stops.

  • 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, January is the cheapest month in which you can book a flight from Cleveland to Chesapeake (average of $281). Flying from Cleveland to Chesapeake in March is currently the most expensive (average of $351). 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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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 septembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$295FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$362FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$369FlexibilityNo cancel feeOn-time71%
DeltaCheapest$202Average$263FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$205Average$328FlexibilityNo cancel feeOn-time63%

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