Chesapeake

$59+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — RIC
Jun 3 — Jun 101
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.

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 May 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:49 pm
CLE
-
ORF
1 stop14h 22m
Frontier
Sat 5/3012:00 pm
ORF
-
CLE
1 stop6h 27m
Frontier
Deal found 5/1$121
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/17:24 pm
CLE
-
ORF
1 stop15h 47m
Frontier
Fri 6/512:06 pm
ORF
-
CLE
1 stop6h 21m
Frontier
Deal found 5/4$124
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/247:24 pm
CLE
-
ORF
1 stop16h 02m
Frontier
Sun 6/2812:21 pm
ORF
-
CLE
1 stop23h 31m
Frontier
Deal found 4/30$126
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/185:51 pm
CLE
-
ORF
1 stop17h 35m
Frontier
Mon 6/229:35 pm
ORF
-
CLE
1 stop10h 22m
Frontier
Deal found 5/3$147
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/266:01 pm
CLE
-
ORF
1 stop17h 10m
Frontier
Fri 5/299:12 pm
ORF
-
CLE
1 stop10h 48m
Frontier
Deal found 4/29$149
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/197:24 pm
CLE
-
ORF
1 stop15h 57m
Frontier
Mon 6/229:35 pm
ORF
-
CLE
1 stop10h 22m
Frontier
Deal found 4/30$150
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/197:24 pm
CLE
-
ORF
1 stop15h 57m
Frontier
Sun 6/2112:21 pm
ORF
-
CLE
1 stop8h 34m
Frontier
Deal found 4/30$155
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/227:24 pm
CLE
-
ORF
1 stop16h 02m
Frontier
Thu 6/2512:21 pm
ORF
-
CLE
1 stop8h 34m
Frontier
Deal found 4/30$158
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/57:24 pm
CLE
-
ORF
1 stop15h 51m
Frontier
Sun 6/79:12 pm
ORF
-
CLE
1 stop10h 36m
Frontier
Deal found 4/30$163

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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$121
(Kiwi.com)

One-way from

$59
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$293
Provider with most accurate pricing for Cleveland Hopkins Intl-Norfolk flight deals.
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Norfolk flights.
From Cleveland Hopkins Intl to Chesapeake
One-way flight from Cleveland Hopkins Intl to Chesapeake
Highest demand for flights based on searches. 12% potential increase in price ($47 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 4, 2026.
Use the filters below to find and compare flights from Cleveland to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 5/23

5:17 pm-11:15 pm

1 stop5h 58m

Norfolk

Mon 5/25

6:00 am-9:20 am

1 stop3h 20m

$311

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 6/10

3:25 pm-10:35 pm

2 stops7h 10m

Norfolk

Sat 6/13

3:10 pm-10:15 pm

2 stops7h 05m

$339

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 7/2

6:45 am-11:27 am

1 stop4h 42m

Norfolk

Mon 7/6

6:43 pm-12:14 am

1 stop5h 31m

$347

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 6/20

7:05 am-5:05 pm

2 stops10h 00m

Norfolk

Mon 6/22

4:30 pm-8:40 pm

1 stop4h 10m

$352

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 7/22

7:05 am-3:50 pm

2 stops8h 45m

Norfolk

Mon 7/27

3:30 pm-11:25 pm

2 stops7h 55m

$357

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 7/29

3:25 pm-10:35 pm

2 stops7h 10m

Norfolk

Fri 7/31

7:05 am-3:20 pm

2 stops8h 15m

$357

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Thu 7/2

4:45 pm-11:35 pm

2 stops6h 50m

Norfolk

Mon 7/6

3:30 pm-12:15 am

2 stops8h 45m

$357

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Sat 6/13

7:05 am-5:05 pm

2 stops10h 00m

Norfolk

Sat 6/20

3:10 pm-10:15 pm

2 stops7h 05m

$367

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 5/20

10:00 am-2:24 pm

1 stop4h 24m

Norfolk

Tue 6/2

10:25 am-3:48 pm

1 stop5h 23m

$369

ClevelandNorfolk

CLE - ORF

CLEORF

Cleveland Hopkins Intl

Wed 6/3

3:19 pm-11:44 pm

2 stops8h 25m

Norfolk

Mon 6/8

4:57 pm-11:45 pm

1 stop6h 48m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 20 resultsSorted by cheapest first
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 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 May 4, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 58m. Fly via Delta or Southwest to get the fastest option. Airlines will cover a distance of 434 mi. This flight may include one or multiple stops.

  • 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 $61 on Frontier. Other airlines that offer cheap prices include Delta from $113 and American Airlines from $118 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.

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.

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 May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$309FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$141Average$372FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$196Average$410FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$239Average$366FlexibilityNo cancel feeOn-time69%

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.