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Chesapeake

$68+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 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 stop19h 55m
Frontier
Deal found 1/27$133
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/268:46 pm
CLE
-
ORF
1 stop13h 51m
Multiple Airlines
Thu 3/57:31 pm
ORF
-
CLE
1 stop30h 11m
Multiple Airlines
Deal found 1/28$147
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/88:48 pm
CLE
-
ORF
1 stop14h 00m
Multiple Airlines
Tue 2/107:33 pm
ORF
-
CLE
1 stop24h 10m
Multiple Airlines
Deal found 1/27$172
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/212:40 pm
CLE
-
ORF
1 stop19h 57m
Frontier
Tue 2/241:02 pm
ORF
-
CLE
1 stop10h 07m
Frontier
Deal found 1/28$175
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/212:40 pm
CLE
-
ORF
1 stop19h 57m
Multiple Airlines
Tue 2/247:31 pm
ORF
-
CLE
2 stops19h 05m
Multiple Airlines
Deal found 1/28$179
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/212:40 pm
CLE
-
ORF
1 stop19h 57m
Frontier
Mon 2/2311:39 am
ORF
-
CLE
2 stops12h 17m
Frontier
Deal found 1/27$180
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/167:04 pm
CLE
-
ORF
1 stop23h 22m
Multiple Airlines
Fri 2/2011:32 am
ORF
-
CLE
1 stop11h 39m
Multiple Airlines
Deal found 1/27$181
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:55 am
CLE
-
ORF
1 stop11h 31m
Multiple Airlines
Wed 2/257:31 pm
ORF
-
CLE
1 stop18h 32m
Multiple Airlines
Deal found 1/27$199

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$133
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$405
Provider with most accurate pricing for Cleveland Hopkins Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Norfolk flights.
Search Deals
From Cleveland Hopkins Intl to Chesapeake
Search Deals
One-way flight from Cleveland Hopkins Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 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

Thu 2/19

8:46 pm-10:37 am

1 stop13h 51m

Norfolk

Mon 2/23

11:39 am-7:34 am

1 stop19h 55m

$133

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 2/26

8:46 pm-10:37 am

1 stop13h 51m

Norfolk

Thu 3/5

6:45 am-12:38 am

2 stops17h 53m

$176

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 2/16

7:04 pm-6:26 pm

1 stop23h 22m

Norfolk

Fri 2/20

11:32 am-11:11 pm

1 stop11h 39m

$181

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 2/23

6:29 pm-12:05 pm

1 stop17h 36m

Norfolk

Wed 2/25

7:31 pm-7:56 am

2 stops12h 25m

$205

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 3/16

5:30 am-11:38 am

1 stop6h 08m

Norfolk

Thu 3/19

11:50 am-11:11 pm

1 stop11h 21m

$218

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 3/12

6:01 pm-10:42 am

1 stop16h 41m

Norfolk

Mon 3/16

8:41 pm-2:37 pm

1 stop17h 56m

$252

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 3/12

6:01 pm-10:42 am

1 stop16h 41m

Norfolk

Mon 3/16

12:33 pm-12:06 pm

1 stop23h 33m

$253

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 2/21

2:32 pm-7:27 pm

1 stop4h 55m

Norfolk

Tue 2/24

7:03 am-11:43 am

1 stop4h 40m

$255

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 3/13

5:30 am-10:32 pm

1 stop17h 02m

Norfolk

Fri 3/20

6:45 am-1:13 am

1 stop18h 28m

$275

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 3/2

5:44 pm-6:26 pm

1 stop24h 42m

$78

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 January 23, 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 January 29, 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
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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 13h 51m. Fly via Frontier to get the fastest option. Airlines will cover a distance of 434 mi.

  • 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 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.

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$105Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$303FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$153Average$348FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$310FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$318FlexibilityNo cancel feeOn-time63%

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