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Chesapeake

$99+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$159
(Expedia)

One-way from

$99
(Delta)

Popular in

January

Cheapest in

April

Average price

$381
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. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 January 12, 2026.

This Expedia deal was found by Cheapflights users on 1/11. 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.
Sun 2/83:23 pmCLE - ORF
1 stop5h 29mFrontier
Tue 2/101:02 pmORF - CLE
1 stop10h 07mFrontier
Deal found 1/11$159
This Expedia deal was found by Cheapflights users on 1/10. 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.
Sun 1/2510:56 amCLE - ORF
1 stop9h 56mFrontier
Thu 1/294:01 pmORF - CLE
1 stop8h 42mFrontier
Deal found 1/10$170
This Travelocity deal was found by Cheapflights users on 1/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:55 pmCLE - ORF
1 stop22h 57mFrontier
Sun 3/111:32 amORF - CLE
1 stop11h 47mFrontier
Deal found 1/11$190
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 2/142:40 pmCLE - ORF
1 stop19h 57mMultiple Airlines
Wed 2/187:31 pmORF - CLE
1 stop22h 38mMultiple Airlines
Deal found 1/11$193
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 2/57:21 pmCLE - ORF
1 stop23h 17mSpirit Airlines
Mon 2/97:33 pmORF - CLE
1 stop22h 24mSpirit Airlines
Deal found 1/11$194
This Delta deal was found by Cheapflights users on 1/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 amCLE - ORF
1 stop7h 13mDelta
Tue 2/2411:25 amORF - CLE
1 stop3h 59mDelta
Deal found 1/11$197
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/97:10 amCLE - ORF
2 stops11h 28mMultiple Airlines
Wed 2/187:31 pmORF - CLE
1 stop22h 38mMultiple Airlines
Deal found 1/10$198
This Mytrip deal was found by Cheapflights users on 1/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/66:00 pmCLE - ORF
1 stop26h 15mFrontier
Sun 2/811:45 amORF - CLE
1 stop11h 26mFrontier
Deal found 1/11$199
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 1/257:01 pmCLE - ORF
2 stops15h 47mMultiple Airlines
Thu 1/297:33 pmORF - CLE
1 stop22h 33mMultiple Airlines
Deal found 1/10$215
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 2/87:15 amCLE - ORF
1 stop13h 37mMultiple Airlines
Tue 2/107:33 pmORF - CLE
2 stops19h 03mMultiple Airlines
Deal found 1/11$225
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 2/277:10 amCLE - ORF
2 stops11h 16mMultiple Airlines
Mon 3/27:31 pmORF - CLE
1 stop24h 12mMultiple Airlines
Deal found 1/11$232

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 12, 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

Sun 2/8

3:23 pm-8:52 pm

1 stop5h 29m

Norfolk

Tue 2/10

1:02 pm-11:09 pm

1 stop10h 07m

$159

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 2/27

4:55 pm-3:52 pm

1 stop22h 57m

Norfolk

Sun 3/1

11:32 am-11:19 pm

1 stop11h 47m

$190

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 2/21

7:05 am-2:23 pm

1 stop7h 18m

Norfolk

Tue 2/24

11:25 am-3:24 pm

1 stop3h 59m

$197

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 2/9

7:10 am-6:38 pm

2 stops11h 28m

Norfolk

Wed 2/18

7:31 pm-6:09 pm

1 stop22h 38m

$198

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 2/14

8:50 am-9:36 pm

2 stops12h 46m

Norfolk

Wed 2/18

7:31 pm-6:09 pm

1 stop22h 38m

$220

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 2/27

7:10 am-6:26 pm

2 stops11h 16m

Norfolk

Mon 3/2

7:31 pm-7:43 pm

1 stop24h 12m

$232

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 2/5

7:10 am-9:50 pm

2 stops14h 40m

Norfolk

Mon 2/9

7:33 pm-7:43 pm

1 stop24h 10m

$235

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 2/14

4:16 pm-9:11 pm

1 stop4h 55m

Norfolk

Wed 2/18

6:20 am-9:50 am

1 stop3h 30m

$257

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 2/6

7:21 pm-1:26 pm

2 stops18h 05m

Norfolk

Sun 2/8

11:45 am-11:11 pm

1 stop11h 26m

$264

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 2/21

4:35 pm-11:00 pm

1 stop6h 25m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 18 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 9, 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 January 12, 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
4,253 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
8,034 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
9,143 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
11,108 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
3,055 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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 5h 29m. 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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$290FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$353FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$309FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$316FlexibilityNo cancel feeOn-time63%
DeltaCheapest$214Average$303FlexibilityNo cancel feeOn-timeN/A

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