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Chesapeake

$82+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 4, 2025.

This Frontier deal was found by Cheapflights users on 12/2. 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 Frontier 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 1/22:34 pmORF - CLE
1 stop8h 39mFrontier
Deal found 12/2$163
This Frontier deal was found by Cheapflights users on 12/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:38 amCLE - ORF
1 stop5h 38mFrontier
Fri 1/22:34 pmORF - CLE
1 stop8h 39mFrontier
Deal found 12/2$208
This Frontier deal was found by Cheapflights users on 12/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:35 amCLE - ORF
1 stop8h 41mFrontier
Fri 1/22:34 pmORF - CLE
1 stop8h 39mFrontier
Deal found 12/2$214
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/116:00 amCLE - ORF
1 stop16h 58mMultiple Airlines
Wed 12/177:00 amORF - CLE
1 stop29h 56mMultiple Airlines
Deal found 12/3$221
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/158:53 pmCLE - ORF
1 stop18h 48mMultiple Airlines
Sat 12/203:01 pmORF - CLE
1 stop8h 50mMultiple Airlines
Deal found 12/3$225
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/116:00 amCLE - ORF
1 stop16h 58mMultiple Airlines
Tue 12/167:00 amORF - CLE
2 stops29h 11mMultiple Airlines
Deal found 12/3$230
This Frontier deal was found by Cheapflights users on 12/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2011:26 amCLE - ORF
1 stop5h 01mFrontier
Wed 12/2411:44 amORF - CLE
1 stop11h 29mFrontier
Deal found 12/2$233
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/182:13 pmCLE - ORF
1 stop8h 45mMultiple Airlines
Mon 12/223:01 pmORF - CLE
1 stop19h 36mMultiple Airlines
Deal found 12/2$238
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/1110:54 amCLE - ORF
2 stops12h 04mMultiple Airlines
Mon 12/157:00 amORF - CLE
1 stop28h 39mMultiple Airlines
Deal found 12/3$240
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/117:17 pmCLE - ORF
1 stop17h 48mMultiple Airlines
Sun 12/148:11 pmORF - CLE
2 stops17h 13mMultiple Airlines
Deal found 12/2$250

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 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$128
(Kiwi.com)

One-way from

$82
(Priceline)

Popular in

December

Cheapest in

April

Average price

$379
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. 9% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 4, 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

Wed 1/7

12:06 pm-6:45 pm

1 stop6h 39m

Norfolk

Sat 1/10

6:45 am-12:26 am

1 stop17h 41m

$129

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/13

4:54 pm-6:25 pm

1 stop25h 31m

Norfolk

Tue 1/20

8:05 am-1:44 pm

1 stop29h 39m

$142

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/13

4:54 pm-6:25 pm

1 stop25h 31m

Norfolk

Tue 1/27

8:05 am-1:44 pm

1 stop29h 39m

$142

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/20

8:49 am-2:32 pm

1 stop5h 43m

Norfolk

Tue 2/3

6:30 am-1:18 pm

1 stop6h 48m

$159

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/13

5:35 am-4:45 pm

2 stops11h 10m

Norfolk

Tue 1/20

12:45 pm-8:50 pm

2 stops8h 05m

$179

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 1/6

8:49 am-2:27 pm

1 stop5h 38m

Norfolk

Fri 1/9

4:12 pm-10:30 pm

1 stop6h 18m

$197

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sun 2/8

8:30 am-6:38 pm

1 stop10h 08m

Norfolk

Tue 2/10

1:10 pm-9:58 am

2 stops20h 48m

$197

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 2/9

5:45 am-3:35 pm

2 stops9h 50m

Norfolk

Tue 2/10

8:50 am-3:05 pm

1 stop6h 15m

$204

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 1/7

4:31 pm-9:30 pm

1 stop4h 59m

Norfolk

Fri 1/9

7:45 am-3:23 pm

1 stop7h 38m

$206

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 1/16

5:02 pm-10:06 pm

1 stop5h 04m

Norfolk

Mon 1/19

7:01 am-11:49 am

1 stop4h 48m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 18 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 November 28, 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 4, 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 4, 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
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,011 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
9,066 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
11,047 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
3,091 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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.

  • How long is the flight from Cleveland to Chesapeake?

    There are many flights that can get you from Cleveland to Chesapeake in 5h 43m. Fly via United Airlines to get the fastest option. Airlines will cover a distance of 434 mi.

  • 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$290FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$354FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$314FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$321FlexibilityNo cancel feeOn-time63%
DeltaCheapest$214Average$302FlexibilityNo cancel feeOn-timeN/A

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