HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$86+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cleveland to Chesapeake with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

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 November 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:33 pmCLE - ORF
1 stop17h 27mMultiple Airlines
Sun 12/148:11 pmORF - CLE
1 stop13h 38mMultiple Airlines
Deal found 11/18$181
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:14 pmCLE - ORF
1 stop28h 02mMultiple Airlines
Mon 12/155:40 pmORF - CLE
1 stop5h 28mMultiple Airlines
Deal found 11/18$189
This Frontier deal was found by Cheapflights users on 11/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:14 amCLE - ORF
1 stop9h 06mFrontier
Mon 12/222:04 pmORF - CLE
1 stop9h 23mFrontier
Deal found 11/18$196
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1210:54 amCLE - ORF
1 stop8h 22mSpirit Airlines
Sat 12/138:11 pmORF - CLE
1 stop13h 38mSpirit Airlines
Deal found 11/18$216
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:41 pmCLE - ORF
2 stops30h 50mMultiple Airlines
Sat 12/68:11 pmORF - CLE
1 stop13h 38mMultiple Airlines
Deal found 11/18$227
This Priceline deal was found by Cheapflights users on 11/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:30 amCLE - ORF
1 stop7h 09mFrontier
Sat 12/275:47 pmORF - CLE
1 stop5h 31mFrontier
Deal found 11/18$230
This Delta deal was found by Cheapflights users on 11/18. 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.
Wed 12/105:35 pmCLE - ORF
1 stop5h 25mDelta
Wed 12/1710:38 amORF - CLE
1 stop5h 28mDelta
Deal found 11/18$257
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1210:54 amCLE - ORF
2 stops11h 24mMultiple Airlines
Sat 12/138:11 pmORF - CLE
1 stop13h 38mMultiple Airlines
Deal found 11/18$260

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 November 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$110
(Frontier)

One-way from

$86
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$316
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 November 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 November 19, 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

Mon 1/26

1:20 pm-10:42 pm

1 stop9h 22m

Norfolk

Thu 1/29

4:01 pm-11:59 pm

1 stop7h 58m

$167

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 1/29

12:30 pm-9:50 pm

1 stop9h 20m

Norfolk

Mon 2/2

7:31 pm-11:59 pm

2 stops28h 28m

$174

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 12/11

5:33 pm-11:00 am

1 stop17h 27m

Norfolk

Sun 12/14

8:11 pm-9:49 am

1 stop13h 38m

$181

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 12/12

3:14 pm-7:16 pm

1 stop28h 02m

Norfolk

Mon 12/15

5:40 pm-11:08 pm

1 stop5h 28m

$189

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 1/10

7:10 am-9:50 pm

2 stops14h 40m

Norfolk

Sun 1/18

7:00 am-1:38 am

1 stop18h 38m

$217

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 12/2

1:41 pm-8:31 pm

2 stops30h 50m

Norfolk

Sat 12/6

8:11 pm-9:49 am

1 stop13h 38m

$227

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 12/10

5:35 pm-11:00 pm

1 stop5h 25m

Norfolk

Wed 12/17

10:38 am-4:06 pm

1 stop5h 28m

$257

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Fri 12/12

10:54 am-10:18 pm

2 stops11h 24m

Norfolk

Sat 12/13

8:11 pm-9:49 am

1 stop13h 38m

$260

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Tue 12/9

11:40 am-4:45 pm

1 stop5h 05m

Norfolk

Thu 12/11

6:15 pm-10:05 pm

1 stop3h 50m

$269

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 12/4

5:33 pm-7:16 pm

2 stops25h 43m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 19 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 14, 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 February is currently the most expensive (average of $218). 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 November 19, 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 November 19, 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
4,249 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,004 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,025 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,046 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,106 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • 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 February is currently the most expensive (average of $218). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cleveland to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Detroit to Dulles Intl flights
Detroit to Reagan-National flights
Detroit to Raleigh flights
Cincinnati to Dulles Intl flights
Pittsburgh to Dulles Intl flights
Cincinnati to Reagan-National flights
Columbus to Dulles Intl flights
Cleveland to Reagan-National flights
Cleveland to Dulles Intl flights
Detroit to Richmond flights
Columbus to Raleigh flights
Pittsburgh to Reagan-National flights
Cincinnati to Raleigh flights
Cleveland to Raleigh flights
Akron to Raleigh flights
Columbus to Reagan-National flights
Detroit to Norfolk flights
Akron to Reagan-National flights
Dayton to Reagan-National flights
Columbus to Greensboro flights
Akron to Dulles Intl flights
Dayton to Dulles Intl flights
Cleveland to Norfolk flights
Detroit to Greensboro flights
Pittsburgh to Norfolk flights
Cincinnati to Greensboro flights
Pittsburgh to Raleigh flights
Cleveland to Greensboro flights
Columbus to Richmond flights
Pittsburgh to Richmond flights
Dayton to Richmond flights
Cincinnati to Norfolk flights
Dayton to Raleigh flights
Cleveland to Richmond flights
Pittsburgh to Greensboro flights
Dayton to Norfolk flights
Columbus to Norfolk flights
Cincinnati to Richmond flights
Pittsburgh to Blountville flights
Akron to Norfolk flights
Detroit to Roanoke flights
Pittsburgh to Roanoke flights
Detroit to Charlottesville flights
Cleveland to Roanoke flights
Erie to Raleigh flights
Detroit to Lynchburg flights
Columbus to Blountville flights
Akron to Richmond flights
Detroit to Blountville flights
Erie to Reagan-National flights

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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$155Average$290FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$193Average$351FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$365FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$205Average$321FlexibilityNo cancel feeOn-time63%
DeltaCheapest$214Average$297FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.