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Chesapeake

$73+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chesapeake are usually found in April or September, 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 August 18, 2025.

Round-trip from

$154
(Frontier)

One-way from

$73
(Priceline)

Popular in

January

Cheapest in

April

Average price

$285
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 ($68 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 August 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 August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/1611:40 amCLE - ORF
1 stop3h 20mSouthwest
Tue 9/236:05 amORF - CLE
1 stop4h 55mSouthwest
Deal found 8/17$157
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:03 pmCLE - ORF
1 stop16h 21mFrontier
Sun 10/55:47 pmORF - CLE
1 stop19h 27mFrontier
Deal found 8/17$160
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:30 amCLE - ORF
1 stop5h 54mFrontier
Mon 9/812:19 pmORF - CLE
1 stop24h 16mFrontier
Deal found 8/18$165
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:44 pmCLE - ORF
1 stop21h 02mFrontier
Thu 10/2312:49 pmORF - CLE
1 stop22h 53mFrontier
Deal found 8/17$166
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:34 pmCLE - ORF
1 stop15h 50mFrontier
Mon 9/2912:19 pmORF - CLE
1 stop12h 24mFrontier
Deal found 8/17$171
This Southwest deal was found by Cheapflights users on 8/17. 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.
Wed 9/1711:40 amCLE - ORF
1 stop5h 35mSouthwest
Mon 9/227:30 pmORF - CLE
1 stop3h 40mSouthwest
Deal found 8/17$177
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 9/113:30 pmCLE - ORF
2 stops7h 20mSouthwest
Tue 9/166:05 amORF - CLE
1 stop4h 55mSouthwest
Deal found 8/17$182
This Southwest deal was found by Cheapflights users on 8/18. 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.
Wed 10/86:35 amCLE - ORF
2 stops9h 20mSouthwest
Wed 10/155:35 amORF - CLE
1 stop6h 55mSouthwest
Deal found 8/18$188
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:30 amCLE - ORF
1 stop5h 54mMultiple Airlines
Sat 9/135:20 amORF - CLE
1 stop10h 30mMultiple Airlines
Deal found 8/17$190
This Orbitz deal was found by Cheapflights users on 8/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/255:30 amCLE - ORF
1 stop5h 54mFrontier
Sun 9/2812:14 pmORF - CLE
2 stops12h 21mFrontier
Deal found 8/17$196
This Delta deal was found by Cheapflights users on 8/18. 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 9/277:07 amCLE - ORF
1 stop7h 24mDelta
Sat 10/411:41 amORF - CLE
1 stop7h 05mDelta
Deal found 8/18$197

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 August 18, 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

Thu 9/4

5:30 am-11:24 am

1 stop5h 54m

Norfolk

Sun 9/7

5:47 pm-1:14 pm

1 stop19h 27m

$154

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 9/16

11:40 am-3:00 pm

1 stop3h 20m

Norfolk

Tue 9/23

6:05 am-11:00 am

1 stop4h 55m

$157

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 10/8

5:45 am-9:10 am

1 stop3h 25m

Norfolk

Wed 10/15

6:25 pm-10:45 pm

1 stop4h 20m

$157

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 9/23

7:05 am-1:35 pm

1 stop6h 30m

Norfolk

Sat 9/27

6:20 am-12:10 pm

1 stop5h 50m

$157

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 10/1

2:00 pm-4:12 pm

1 stop26h 12m

Norfolk

Sun 10/5

12:14 pm-10:39 am

1 stop22h 25m

$160

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sun 9/14

5:30 am-11:19 am

1 stop5h 49m

Norfolk

Sun 9/21

5:47 pm-8:55 pm

1 stop27h 08m

$160

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 10/15

8:00 am-9:02 am

1 stop25h 02m

Norfolk

Sun 10/19

4:14 pm-10:47 am

1 stop18h 33m

$160

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 9/5

5:30 am-11:24 am

1 stop5h 54m

$73

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sun 9/14

5:30 am-11:19 am

1 stop5h 49m

$73

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sun 9/21

5:30 am-11:19 am

1 stop5h 49m

$73

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 14 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 August 8, 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 August 18, 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 August 18, 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
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 3h 20m. Fly via Frontier 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.

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$295FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$399FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$368FlexibilityNo cancel feeOn-time71%
DeltaCheapest$202Average$279FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$205Average$325FlexibilityNo cancel feeOn-time63%

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