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Chesapeake

$52+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chesapeake are usually found in July or May, booked 65 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 June 16, 2025.

Round-trip from

$99
(Cheapflightsfares)

One-way from

$52
(Trip.com)

Popular in

April

Cheapest in

July

Average price

$241
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 June 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 June 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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.
Thu 7/174:43 pmMCO - ORF
Nonstop2h 11mFrontier
Thu 7/247:39 pmORF - MCO
Nonstop2h 14mFrontier
Deal found 6/14$99
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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.
Thu 8/74:43 pmMCO - ORF
Nonstop2h 11mMultiple Airlines
Mon 8/115:50 amORF - MCO
Nonstop2h 05mMultiple Airlines
Deal found 6/14$107
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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.
Fri 7/411:02 amMCO - ORF
Nonstop1h 54mSpirit Airlines
Thu 7/105:50 amORF - MCO
Nonstop2h 05mSpirit Airlines
Deal found 6/14$108
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:00 amMCO - ORF
1 stop5h 27mDelta
Mon 9/227:00 amORF - MCO
1 stop7h 37mDelta
Deal found 6/14$167
This Southwest deal was found by Cheapflights users on 6/16. 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 8/2810:45 amMCO - ORF
2 stops7h 55mSouthwest
Tue 9/23:45 pmORF - MCO
Nonstop2h 05mSouthwest
Deal found 6/16$172
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/227:25 pmMCO - ORF
1 stop4h 34mAmerican Airlines
Mon 8/256:10 amORF - MCO
1 stop4h 04mAmerican Airlines
Deal found 6/14$198
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/242:30 pmMCO - ORF
2 stops9h 20mUnited Airlines
Mon 9/297:59 pmORF - MCO
1 stop4h 46mUnited Airlines
Deal found 6/14$276

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 June 16, 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 7/17

4:43 pm-6:54 pm

Nonstop2h 11m

Norfolk

Thu 7/24

7:39 pm-9:53 pm

Nonstop2h 14m

$99

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 8/7

4:43 pm-6:54 pm

Nonstop2h 11m

Norfolk

Mon 8/11

5:50 am-7:55 am

Nonstop2h 05m

$107

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 7/4

11:02 am-12:56 pm

Nonstop1h 54m

Norfolk

Thu 7/10

5:50 am-7:55 am

Nonstop2h 05m

$108

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 8/15

6:20 am-2:15 pm

1 stop7h 55m

Norfolk

Sun 8/17

5:30 pm-7:35 pm

Nonstop2h 05m

$157

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 9/18

6:00 am-11:27 am

1 stop5h 27m

Norfolk

Mon 9/22

7:00 am-2:37 pm

1 stop7h 37m

$167

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 8/22

7:25 pm-11:59 pm

1 stop4h 34m

Norfolk

Mon 8/25

6:10 am-10:14 am

1 stop4h 04m

$198

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Wed 9/24

12:16 pm-11:50 pm

2 stops11h 34m

Norfolk

Tue 9/30

7:59 pm-12:45 am

1 stop4h 46m

$276

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 7/4

11:02 am-12:56 pm

Nonstop1h 54m

$52

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 8/14

4:43 pm-6:54 pm

Nonstop2h 11m

$59

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Tue 9/9

9:05 am-11:00 am

Nonstop1h 55m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 15 results
1
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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 June 13, 2025.

To ensure you get the cheapest price possible for a flight from Orlando to Chesapeake, you should look to book at least 49 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 June 16, 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 June 15, 2025.

Travelers seeking maximum savings on their Orlando to Chesapeake flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday at noon 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 June 16, 2025.

The most flights from ORL to C6E are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 June 16, 2025.
Read through reviews of airlines operating flights from Orlando to Chesapeake, such as Breeze Airways, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
181 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,278 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,963 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,801 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 cheapest airlines to fly from Orlando to Chesapeake one-way?

    $52 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Southwest, with prices starting from $59 and $79, respectively.

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

    The top 3 most reliable airlines when flying from Orlando to Chesapeake are JetBlue (90%), Azul (87%) and Spirit Airlines (67%).

  • What are the cheapest flights from Orlando to Chesapeake?

    While on average a flight from Orlando to Chesapeake is generally $144, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Orlando - Norfolk), you can expect to pay $107 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.

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$33Average$127FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$130FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$101FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$93Average$222FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$261FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$137Average$302FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$158Average$294FlexibilityNo cancel feeOn-time71%

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