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Chesapeake

$76+ 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 20 — Jan 271
Tue 1/20
Tue 1/27
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

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 21, 2025.

This Priceline deal was found by Cheapflights users on 12/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:20 amCLE - ORF
1 stop6h 49mFrontier
Fri 12/262:34 pmORF - CLE
1 stop8h 39mFrontier
Deal found 12/19$283
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/316:20 amCLE - ORF
2 stops31h 46mMultiple Airlines
Mon 1/57:40 pmORF - CLE
1 stop28h 46mMultiple Airlines
Deal found 12/20$319
This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/315:58 pmCLE - ORF
1 stop4h 58mDelta
Mon 1/55:20 amORF - CLE
1 stop4h 57mDelta
Deal found 12/20$330
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/297:59 pmCLE - ORF
2 stops18h 07mMultiple Airlines
Fri 1/22:34 pmORF - CLE
1 stop8h 39mMultiple Airlines
Deal found 12/19$375
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/2311:43 amCLE - ORF
1 stop26h 23mMultiple Airlines
Thu 12/255:27 pmORF - CLE
2 stops29h 46mMultiple Airlines
Deal found 12/19$382
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/2311:43 amCLE - ORF
1 stop26h 23mSpirit Airlines
Thu 12/253:01 pmORF - CLE
1 stop19h 36mSpirit Airlines
Deal found 12/19$407
This Southwest deal was found by Cheapflights users on 12/20. 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 12/316:45 amCLE - ORF
2 stops10h 00mSouthwest
Mon 1/511:35 amORF - CLE
2 stops9h 50mSouthwest
Deal found 12/20$508
This American Airlines deal was found by Cheapflights users on 12/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:31 amCLE - ORF
1 stop7h 35mAmerican Airlines
Mon 12/296:00 amORF - CLE
1 stop9h 14mAmerican Airlines
Deal found 12/19$514
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/226:59 pmCLE - ORF
1 stop19h 17mMultiple Airlines
Fri 12/262:34 pmORF - CLE
2 stops20h 03mMultiple Airlines
Deal found 12/19$522

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 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$160
(Kiwi.com)

One-way from

$76
(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. 13% potential increase in price ($49 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 21, 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-2:33 pm

1 stop29h 32m

Norfolk

Thu 2/26

7:31 pm-6:09 pm

1 stop22h 38m

$149

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 1/8

7:01 pm-6:38 pm

1 stop23h 37m

Norfolk

Mon 1/12

12:25 pm-7:34 am

1 stop19h 09m

$160

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/6

7:10 am-10:45 am

1 stop27h 35m

Norfolk

Thu 1/8

7:00 am-11:54 am

1 stop28h 54m

$170

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 1/7

2:23 pm-6:38 pm

1 stop28h 15m

Norfolk

Mon 1/12

7:33 pm-11:11 pm

2 stops27h 38m

$171

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 1/7

2:23 pm-6:38 pm

1 stop28h 15m

Norfolk

Sun 1/11

7:33 pm-11:54 am

2 stops16h 21m

$174

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 2/2

7:10 am-6:38 pm

2 stops11h 28m

Norfolk

Thu 2/5

7:33 pm-10:44 pm

1 stop27h 11m

$176

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 1/19

12:10 pm-1:31 pm

1 stop25h 21m

Norfolk

Mon 1/26

7:33 pm-1:44 pm

2 stops18h 11m

$187

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 1/29

8:15 am-6:38 pm

1 stop10h 23m

Norfolk

Mon 2/2

7:33 pm-1:44 pm

2 stops18h 11m

$190

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 1/19

6:30 am-6:38 pm

1 stop12h 08m

Norfolk

Fri 1/23

7:33 pm-11:11 pm

2 stops27h 38m

$192

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

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 12, 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.

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 December 21, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 17% on flights from Cleveland to Chesapeake by exploring options for tickets in the evening.

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 Saturday at noon when fares are most often at their lowest. Sunday at noon 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 December 21, 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
4,257 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,021 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
9,099 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
11,050 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
3,082 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$290FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$351FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$310FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$317FlexibilityNo cancel feeOn-time63%
DeltaCheapest$214Average$302FlexibilityNo cancel feeOn-timeN/A

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