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Chesapeake

$100+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$177
(Southwest)

One-way from

$100
(Priceline)

Popular in

January

Cheapest in

April

Average price

$321
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 ($69 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 July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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 8/75:50 amCLE - ORF
1 stop5h 35mSouthwest
Mon 8/115:30 pmORF - CLE
1 stop5h 40mSouthwest
Deal found 7/1$177
This American Airlines deal was found by Cheapflights users on 7/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/95:00 amCLE - ORF
1 stop5h 09mAmerican Airlines
Thu 8/143:40 pmORF - CLE
1 stop6h 45mAmerican Airlines
Deal found 7/2$189
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/263:48 pmCLE - ORF
1 stop6h 47mSpirit Airlines
Sat 8/25:50 amORF - CLE
1 stop9h 03mSpirit Airlines
Deal found 7/2$196
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/114:10 pmCLE - ORF
1 stop6h 05mDelta
Wed 8/138:05 amORF - CLE
1 stop7h 23mDelta
Deal found 7/3$197
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 7/298:50 amCLE - ORF
1 stop6h 24mUnited Airlines
Tue 8/58:10 pmORF - CLE
1 stop3h 49mUnited Airlines
Deal found 7/1$209
This Frontier deal was found by Cheapflights users on 7/2. 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.
Fri 10/35:30 amCLE - ORF
1 stop5h 54mFrontier
Sat 10/113:27 pmORF - CLE
1 stop9h 20mFrontier
Deal found 7/2$227
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/193:48 pmCLE - ORF
2 stops16h 27mMultiple Airlines
Sat 7/265:50 amORF - CLE
1 stop9h 03mMultiple Airlines
Deal found 7/3$265

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 July 3, 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 8/7

5:50 am-11:25 am

1 stop5h 35m

Norfolk

Mon 8/11

5:30 pm-11:10 pm

1 stop5h 40m

$177

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 8/9

5:00 am-10:09 am

1 stop5h 09m

Norfolk

Thu 8/14

3:40 pm-10:25 pm

1 stop6h 45m

$189

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 7/26

3:48 pm-10:35 pm

1 stop6h 47m

Norfolk

Sat 8/2

5:50 am-2:53 pm

1 stop9h 03m

$196

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 8/11

4:10 pm-10:15 pm

1 stop6h 05m

Norfolk

Wed 8/13

8:05 am-3:28 pm

1 stop7h 23m

$197

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 7/29

8:50 am-3:14 pm

1 stop6h 24m

Norfolk

Tue 8/5

8:10 pm-11:59 pm

1 stop3h 49m

$209

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 7/19

3:48 pm-8:15 am

2 stops16h 27m

Norfolk

Sat 7/26

5:50 am-2:53 pm

1 stop9h 03m

$265

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 7/10

11:04 am-6:54 pm

1 stop7h 50m

Norfolk

Sun 7/13

12:53 pm-11:20 pm

1 stop10h 27m

$274

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 8/2

3:48 pm-10:35 pm

1 stop6h 47m

$100

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Mon 9/15

8:00 pm-11:50 pm

1 stop3h 50m

$119

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 7/12

4:18 pm-8:15 am

1 stop15h 57m

$122

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 15 results
1
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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 June 27, 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 July 3, 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.

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 July 3, 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
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $100 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $119 and American Airlines from $126 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, 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.

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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$270FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$386FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$216Average$328FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time71%
DeltaCheapest$226Average$282FlexibilityNo cancel feeOn-timeN/A

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