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Chesapeake

$67+ 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
أبريل 28 — مايو 51
ث 4/28
ث 5/5
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 مارس 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
ج 5/13:46 pm
CLE
-
ORF
1 stop18h 46m
Frontier
ث 5/512:06 pm
ORF
-
CLE
1 stop23h 44m
Frontier
Deal found 3/26$126
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
ن 5/117:24 pm
CLE
-
ORF
1 stop15h 47m
Frontier
ر 5/1312:06 pm
ORF
-
CLE
1 stop6h 21m
Frontier
Deal found 3/24$131
This Expedia deal was found by Cheapflights users on 3/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
خ 4/1610:00 pm
CLE
-
ORF
1 stop19h 27m
Frontier
س 4/1811:27 am
ORF
-
CLE
1 stop6h 28m
Frontier
Deal found 3/25$140
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
ر 4/2211:46 am
CLE
-
ORF
1 stop22h 46m
Frontier
ن 4/2711:27 am
ORF
-
CLE
1 stop20h 17m
Frontier
Deal found 3/27$146
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
س 4/259:05 pm
CLE
-
ORF
1 stop12h 00m
Frontier
س 5/211:27 am
ORF
-
CLE
1 stop6h 28m
Frontier
Deal found 3/25$156
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
ن 5/44:22 pm
CLE
-
ORF
1 stop18h 49m
Frontier
خ 5/79:12 pm
ORF
-
CLE
1 stop10h 22m
Frontier
Deal found 3/28$160
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
ر 6/37:24 pm
CLE
-
ORF
1 stop15h 47m
Frontier
ر 6/1012:21 pm
ORF
-
CLE
1 stop6h 08m
Frontier
Deal found 3/28$165

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 مارس 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$126
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$441
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 ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 مارس 29, 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

Price

Cheapest round-trip

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

س 4/18

5:30 am-6:21 pm

1 stop12h 51m

Norfolk

ث 4/21

8:05 am-2:26 pm

2 stops30h 21m

$241

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

س 4/18

7:20 am-3:25 pm

2 stops8h 05m

Norfolk

س 4/18

5:20 pm-11:05 pm

1 stop5h 45m

$300

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

س 4/18

6:05 am-3:25 pm

2 stops9h 20m

Norfolk

ث 4/21

11:10 am-8:20 pm

2 stops9h 10m

$305

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ث 4/14

6:40 am-5:50 pm

2 stops11h 10m

Norfolk

ر 4/22

11:10 am-8:20 pm

2 stops9h 10m

$307

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ر 5/13

8:30 am-2:24 pm

1 stop5h 54m

Norfolk

ن 5/18

6:14 pm-10:44 pm

1 stop4h 30m

$320
Quickest round-trip

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

خ 9/17

7:15 am-11:29 am

1 stop4h 14m

Norfolk

خ 9/17

5:00 pm-8:57 pm

1 stop3h 57m

$347

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ج 8/7

6:05 pm-12:57 am

1 stop6h 52m

Norfolk

خ 8/13

6:20 am-9:36 am

1 stop3h 16m

$347

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

خ 4/16

12:55 pm-10:55 pm

2 stops10h 00m

Norfolk

س 4/18

1:15 pm-9:00 pm

2 stops7h 45m

$351

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

ج 8/7

7:15 am-5:55 pm

2 stops10h 40m

Norfolk

ج 8/14

8:00 am-3:10 pm

1 stop7h 10m

$352

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

خ 8/27

7:15 am-5:55 pm

2 stops10h 40m

Norfolk

س 8/29

3:35 pm-8:55 pm

1 stop5h 20m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 19 resultsSorted by cheapest first
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 March 13, 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 65 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.

How much does it cost to fly round-trip from Cleveland to Chesapeake?

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 مارس 29, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,359 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,509 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,521 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,010 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 03m. Fly via Southwest 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 $61 on Frontier. Other airlines that offer cheap prices include American Airlines from $105 and Southwest from $118 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.

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Alternative routes for Cleveland to Chesapeake

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 مارس 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$105Average$290FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$309FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$404FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$336FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$239Average$364FlexibilityNo cancel feeOn-time69%

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