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Chesapeake

$38+ Cheap flights from Orlando (ORL) 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chesapeake are usually found in May or March, booked 90 days in advance, depart on a Thursday or Monday and return on a Monday

Cheap flight deals from Orlando to Chesapeake

Keep the following information in mind while searching for Orlando to Chesapeake flight deals. Data was last updated August 14, 2025.

Round-trip from

$88
(Cheapflightsfares)

One-way from

$38
(Cheapflightsfares)

Popular in

April

Cheapest in

May

Average price

$160
From Orlando (ORL) to Chesapeake
Search Deals
One-way flight from Orlando (ORL) to Chesapeake
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Orlando to Chesapeake

Cheapest flights from Orlando to Chesapeake
Explore the most affordable flight options available from Orlando to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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.
Thu 9/252:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Sat 9/275:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Deal found 8/12$88
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 9/202:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Mon 9/225:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Deal found 8/14$89
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/52:39 pmMCO - ORF
Nonstop2h 04mMultiple Airlines
Sun 9/75:47 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Deal found 8/13$91
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:26 pmMCO - ORF
Nonstop1h 59mMultiple Airlines
Sun 8/319:52 pmORF - MCO
Nonstop2h 15mMultiple Airlines
Deal found 8/13$93
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:26 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Sun 8/315:34 pmORF - MCO
Nonstop2h 08mSpirit Airlines
Deal found 8/14$94
This Priceline deal was found by Cheapflights users on 8/13. 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.
Wed 8/272:26 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Tue 9/25:20 pmORF - MCO
Nonstop2h 08mSpirit Airlines
Deal found 8/13$96
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/82:39 pmMCO - ORF
Nonstop2h 04mMultiple Airlines
Thu 9/115:12 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Deal found 8/14$97
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/292:26 pmMCO - ORF
Nonstop1h 59mMultiple Airlines
Sun 8/319:52 pmORF - MCO
Nonstop2h 15mMultiple Airlines
Deal found 8/13$98
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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.
Fri 9/262:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Sun 9/285:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Deal found 8/13$99
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/172:39 pmMCO - ORF
Nonstop2h 00mMultiple Airlines
Sun 10/199:47 amORF - MCO
Nonstop2h 08mMultiple Airlines
Deal found 8/13$101
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 9/272:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Sun 9/285:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Deal found 8/14$102
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/272:26 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Sat 8/305:20 pmORF - MCO
Nonstop2h 08mSpirit Airlines
Deal found 8/13$104

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando 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 August 14, 2025.
Use the filters below to find and compare flights from Orlando to Chesapeake that are best for you.

Fly from

Orlando

Fly to

Chesapeake

Route

Depart

Return

Price

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 9/25

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Sat 9/27

5:38 pm-7:48 pm

Nonstop2h 10m

$88

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 9/26

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Sat 9/27

5:38 pm-7:48 pm

Nonstop2h 10m

$89

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 10/2

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Sat 10/4

5:38 pm-7:48 pm

Nonstop2h 10m

$89

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Wed 11/5

10:00 pm-12:07 am

Nonstop2h 07m

Norfolk

Sun 11/9

8:01 am-10:09 am

Nonstop2h 08m

$89

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 9/20

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Mon 9/22

5:38 pm-7:48 pm

Nonstop2h 10m

$89

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 9/5

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Sun 9/7

5:47 pm-7:58 pm

Nonstop2h 11m

$91

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 9/20

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Sun 9/21

5:47 pm-7:58 pm

Nonstop2h 11m

$91

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 9/6

2:39 pm-4:43 pm

Nonstop2h 04m

Norfolk

Sun 9/14

5:47 pm-7:58 pm

Nonstop2h 11m

$91

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 8/30

2:26 pm-4:25 pm

Nonstop1h 59m

Norfolk

Sun 8/31

9:52 pm-12:07 am

Nonstop2h 15m

$93

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sun 9/7

2:50 pm-4:57 pm

Nonstop2h 07m

$38

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 18 results
1
2

Best time to book a flight from Orlando to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Orlando 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 Orlando to Chesapeake

How far ahead should I book a flight from Orlando to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Chesapeake. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Orlando to Chesapeake, you should look to book at least 88 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Orlando to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Orlando to Chesapeake (average of $281). Flying from Orlando 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 ORL to C6E?

Find hourly flight availability from Orlando 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 August 14, 2025.

When flying from Orlando 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 Orlando to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Orlando to Chesapeake. Price data was last updated on August 10, 2025.

Travelers seeking maximum savings on their Orlando to Chesapeake flight should consider departing on Thursday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Orlando to Chesapeake

Explore weekly flight availability from Orlando to Chesapeake. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2025.

The most flights from ORL to C6E are scheduled on a Thursday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Orlando 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 August 14, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Orlando to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,046 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,217 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most reliable airlines from Orlando to Chesapeake?

    The top 3 most reliable airlines when flying from Orlando to Chesapeake are JetBlue (81%), Azul (80%) and Southwest (79%).

  • What are the cheapest flights from Orlando to Chesapeake?

    While on average a flight from Orlando to Chesapeake is generally $121, our data shows the cheapest flight currently is $39. When looking at the most popular route, (Orlando - Norfolk), you can expect to pay $84 for that flight.

  • Can I find deals for flights from Orlando to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Orlando to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Chesapeake.

  • Can I find deals for business class flights from Orlando to Chesapeake?

    Yes. Cheapflights offers flight deals from Orlando 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 Orlando to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Orlando to Chesapeake (average of $281). Flying from Orlando 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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Alternative routes for Orlando to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Orlando to Chesapeake

Discover the top 7 airlines that operate flights from Orlando 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$33Average$129FlexibilityNo cancel feeOn-time65%
FrontierCheapest$59Average$143FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$76Average$111FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$91Average$216FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$117Average$287FlexibilityNo cancel feeOn-time63%
DeltaCheapest$124Average$269FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$305FlexibilityNo cancel feeOn-time71%

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