Chesapeake

$59+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Jun 15 — Jun 221
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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 May 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Mon 8/37:24 pm
CLE
-
ORF
1 stop15h 57m
Frontier
Fri 8/712:21 pm
ORF
-
CLE
1 stop6h 05m
Frontier
Deal found 5/11$121
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 8/17:24 pm
CLE
-
ORF
1 stop15h 57m
Frontier
Sat 8/812:06 pm
ORF
-
CLE
1 stop6h 20m
Frontier
Deal found 5/11$124
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/127:24 pm
CLE
-
ORF
1 stop15h 57m
Frontier
Tue 6/2312:21 pm
ORF
-
CLE
1 stop8h 34m
Frontier
Deal found 5/12$126
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 8/135:51 pm
CLE
-
ORF
1 stop17h 30m
Frontier
Sun 8/1612:21 pm
ORF
-
CLE
1 stop8h 31m
Frontier
Deal found 5/13$147
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Tue 6/95:51 pm
CLE
-
ORF
1 stop17h 35m
Frontier
Tue 6/1612:21 pm
ORF
-
CLE
1 stop8h 34m
Frontier
Deal found 5/12$150
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 7/107:24 pm
CLE
-
ORF
1 stop15h 50m
Frontier
Mon 7/139:35 pm
ORF
-
CLE
2 stops14h 14m
Frontier
Deal found 5/13$167
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 7/235:51 pm
CLE
-
ORF
1 stop17h 30m
Frontier
Tue 7/2812:21 pm
ORF
-
CLE
2 stops12h 23m
Frontier
Deal found 5/13$171
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 6/186:37 am
CLE
-
ORF
1 stop28h 49m
Frontier
Tue 6/2312:21 pm
ORF
-
CLE
2 stops12h 22m
Frontier
Deal found 5/13$177
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/263:46 pm
CLE
-
ORF
1 stop19h 35m
Frontier
Tue 6/3012:21 pm
ORF
-
CLE
1 stop23h 31m
Frontier
Deal found 5/12$182
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/51:00 pm
CLE
-
ORF
2 stops22h 15m
Frontier
Mon 6/812:06 pm
ORF
-
CLE
1 stop6h 21m
Frontier
Deal found 5/12$188

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 May 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$121
(Kiwi.com)

One-way from

$59
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$358
Provider with most accurate pricing for Cleveland Hopkins Intl-Norfolk flight deals.
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Norfolk flights.
From Cleveland Hopkins Intl to Chesapeake
One-way flight from Cleveland Hopkins Intl to Chesapeake
Highest demand for flights based on searches. 18% potential increase in price ($83 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 16, 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

Wed 6/3

2:45 pm-9:55 pm

2 stops7h 10m

Norfolk

Wed 6/10

6:05 am-12:40 pm

2 stops6h 35m

$317

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 7/10

3:46 pm-11:14 am

1 stop19h 28m

Norfolk

Sun 7/12

12:21 pm-12:44 am

2 stops12h 23m

$328

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 7/23

4:45 pm-11:35 pm

2 stops6h 50m

Norfolk

Tue 7/28

6:05 am-12:40 pm

2 stops6h 35m

$330

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 5/22

8:43 am-8:17 pm

1 stop11h 34m

Norfolk

Mon 5/25

12:06 pm-6:27 pm

1 stop6h 21m

$330

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 7/4

10:50 am-8:00 pm

2 stops9h 10m

Norfolk

Mon 7/6

4:30 pm-11:25 pm

2 stops6h 55m

$343
Quickest round-trip

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 7/3

6:00 am-9:39 am

1 stop3h 39m

Norfolk

Fri 7/3

5:00 pm-11:49 pm

1 stop6h 49m

$347

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 6/19

4:45 pm-11:35 pm

2 stops6h 50m

Norfolk

Mon 7/6

4:30 pm-11:25 pm

2 stops6h 55m

$350

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 6/12

4:45 pm-11:35 pm

2 stops6h 50m

Norfolk

Sun 6/14

6:15 pm-11:55 pm

1 stop5h 40m

$352

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sun 7/26

5:45 pm-11:55 pm

1 stop6h 10m

Norfolk

Fri 7/31

6:00 am-2:25 pm

2 stops8h 25m

$352

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 6/12

4:45 pm-11:35 pm

2 stops6h 50m

Norfolk

Sat 6/20

6:00 am-12:50 pm

2 stops6h 50m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 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 May 16, 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.

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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.

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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.

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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.

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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.

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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.

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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 7h 10m. Fly via Southwest or Frontier 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 Delta from $113 and American Airlines 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.

See more FAQs

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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.

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 May 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$308FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$141Average$372FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$196Average$418FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$239Average$366FlexibilityNo cancel feeOn-time69%

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