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Chesapeake

$75+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
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 December 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Wed 12/318:15 pmCLE - ORF
1 stop26h 14mMultiple Airlines
Fri 1/96:45 amORF - CLE
1 stop17h 41mMultiple Airlines
Deal found 12/26$365
This Trip.com deal was found by Cheapflights users on 12/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:20 amCLE - ORF
1 stop6h 49mFrontier
Wed 12/3111:44 amORF - CLE
1 stop11h 29mFrontier
Deal found 12/25$427
This United Airlines deal was found by Cheapflights users on 12/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amCLE - ORF
1 stop8h 12mUnited Airlines
Sat 1/37:55 pmORF - CLE
1 stop4h 00mUnited Airlines
Deal found 12/25$599
This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:50 amCLE - ORF
2 stops9h 40mSouthwest
Fri 1/96:30 amORF - CLE
2 stops10h 40mSouthwest
Deal found 12/26$602
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Mon 12/296:00 amCLE - ORF
1 stop8h 06mMultiple Airlines
Wed 12/3111:44 amORF - CLE
2 stops22h 53mMultiple Airlines
Deal found 12/25$653
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:41 pmCLE - ORF
1 stop4h 37mDelta
Sun 12/285:23 amORF - CLE
1 stop4h 54mDelta
Deal found 12/26$717
This Southwest deal was found by Cheapflights users on 12/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:10 pmCLE - ORF
2 stops8h 25mSouthwest
Wed 12/3110:05 amORF - CLE
2 stops10h 45mSouthwest
Deal found 12/25$727
This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/263:10 pmCLE - ORF
1 stop7h 40mSouthwest
Sun 12/2811:25 amORF - CLE
2 stops7h 55mSouthwest
Deal found 12/26$728
This United Airlines deal was found by Cheapflights users on 12/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:14 pmCLE - ORF
2 stops26h 47mUnited Airlines
Sun 12/287:55 pmORF - CLE
2 stops15h 18mUnited Airlines
Deal found 12/26$1,978

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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$131
(Kiwi.com)

One-way from

$75
(Trip.com)

Popular in

December

Cheapest in

April

Average price

$461
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. 16% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 28, 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 2/19

9:01 am-6:28 pm

1 stop9h 27m

Norfolk

Sun 2/22

7:31 pm-6:09 pm

1 stop22h 38m

$145

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/20

6:00 pm-6:25 pm

1 stop24h 25m

Norfolk

Mon 1/26

7:33 pm-12:43 am

2 stops29h 10m

$184

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/13

4:00 pm-1:26 pm

1 stop21h 26m

Norfolk

Sat 1/17

6:45 am-9:32 pm

2 stops14h 47m

$185

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 2/21

6:15 am-9:50 pm

1 stop15h 35m

Norfolk

Mon 2/23

11:39 am-11:11 pm

1 stop11h 32m

$192

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 2/6

3:22 pm-9:50 pm

1 stop6h 28m

Norfolk

Sun 2/8

9:37 pm-12:43 am

1 stop27h 06m

$207

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 2/5

8:48 pm-6:38 pm

2 stops21h 50m

Norfolk

Thu 2/12

7:13 pm-7:56 am

1 stop12h 43m

$210

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 2/27

7:00 am-1:46 pm

1 stop6h 46m

Norfolk

Mon 3/2

11:39 am-7:54 pm

1 stop8h 15m

$217

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 2/20

7:00 am-2:33 pm

1 stop7h 33m

Norfolk

Sun 2/22

7:31 pm-7:54 pm

2 stops24h 23m

$232

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 1/16

5:30 am-9:50 pm

1 stop16h 20m

Norfolk

Sun 1/18

2:18 pm-12:26 am

1 stop10h 08m

$245

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 2/12

1:33 pm-2:33 pm

1 stop25h 00m

Norfolk

Mon 2/16

11:39 am-7:34 am

1 stop19h 55m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 20 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 December 26, 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, 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 March is currently the most expensive (average of $153). 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 December 28, 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
4,256 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
8,019 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
9,113 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
11,072 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
5.8
Fair
3,065 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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.

  • 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 March is currently the most expensive (average of $153). 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$290FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$351FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$308FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$314FlexibilityNo cancel feeOn-time63%
DeltaCheapest$214Average$303FlexibilityNo cancel feeOn-timeN/A

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