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Chesapeake

$45+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Nov 18 — Nov 251
Tue 11/18
Tue 11/25
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

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 October 19, 2025.

This Expedia deal was found by Cheapflights users on 10/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:52 pmMCO - ORF
Nonstop2h 10mMultiple Airlines
Mon 11/31:19 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Deal found 10/17$98
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Thu 12/48:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Deal found 10/16$100
This Priceline deal was found by Cheapflights users on 10/18. 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.
Thu 11/135:25 amMCO - ORF
1 stop9h 00mFrontier
Sun 11/161:06 pmORF - MCO
Nonstop2h 10mFrontier
Deal found 10/18$106
This Gotogate deal was found by Cheapflights users on 10/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:25 amMCO - ORF
1 stop5h 21mFrontier
Sun 11/91:11 pmORF - MCO
Nonstop2h 10mFrontier
Deal found 10/18$107
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/113:40 pmMCO - ORF
Nonstop1h 58mSpirit Airlines
Fri 11/219:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Deal found 10/18$109
This Priceline deal was found by Cheapflights users on 10/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Wed 12/39:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Deal found 10/16$110
This Expedia deal was found by Cheapflights users on 10/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:52 pmMCO - ORF
Nonstop2h 10mMultiple Airlines
Sun 11/29:03 pmORF - MCO
Nonstop2h 07mMultiple Airlines
Deal found 10/19$124
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:30 amMCO - ORF
1 stop10h 27mSpirit Airlines
Sat 11/156:02 pmORF - MCO
1 stop4h 06mSpirit Airlines
Deal found 10/18$131
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Sun 11/239:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Deal found 10/16$134
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/138:00 amMCO - ORF
1 stop13h 05mMultiple Airlines
Tue 11/186:33 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Deal found 10/18$137
This Priceline deal was found by Cheapflights users on 10/17. 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.
Thu 10/3010:15 amMCO - ORF
Nonstop2h 01mFrontier
Sun 11/21:06 pmORF - MCO
Nonstop2h 10mFrontier
Deal found 10/17$138

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 October 19, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$95
(Expedia)

One-way from

$45
(Kiwi.com)

Popular in

April

Cheapest in

May

Average price

$170
Provider with most accurate pricing for Orlando (ORL)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Norfolk flights.
Search Deals
From Orlando (ORL) to Chesapeake
Search Deals
One-way flight from Orlando (ORL) to Chesapeake
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 19, 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

Fri 12/5

5:46 am-7:43 am

Nonstop1h 57m

Norfolk

Mon 12/8

8:38 am-10:50 am

Nonstop2h 12m

$100

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 11/13

11:13 am-1:15 pm

Nonstop2h 02m

Norfolk

Sun 11/16

1:06 pm-3:16 pm

Nonstop2h 10m

$100

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 11/6

5:25 am-10:46 am

1 stop5h 21m

Norfolk

Sun 11/9

1:11 pm-3:21 pm

Nonstop2h 10m

$107

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 11/21

6:32 pm-8:31 pm

Nonstop1h 59m

Norfolk

Wed 12/3

9:26 pm-11:29 pm

Nonstop2h 03m

$110

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 11/13

8:00 am-9:05 pm

1 stop13h 05m

Norfolk

Tue 11/18

6:33 pm-8:44 pm

Nonstop2h 11m

$137

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Mon 12/8

5:46 am-7:43 am

Nonstop1h 57m

Norfolk

Mon 12/15

5:40 pm-12:21 am

1 stop6h 41m

$145

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 10/31

7:52 pm-10:02 pm

Nonstop2h 10m

Norfolk

Sun 11/2

11:42 am-5:03 pm

1 stop5h 21m

$148

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 2/19

7:05 am-4:50 pm

1 stop9h 45m

Norfolk

Sat 2/21

8:32 pm-10:42 pm

Nonstop2h 10m

$151

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 12/6

8:55 am-10:50 am

Nonstop1h 55m

Norfolk

Mon 12/8

4:10 pm-6:15 pm

Nonstop2h 05m

$153

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Wed 1/21

5:30 pm-7:37 pm

Nonstop2h 07m

$45

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 19 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 October 17, 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 $38). Flying from Orlando to Chesapeake in June is currently the most expensive (average of $87). 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 October 19, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 39% on flights from Orlando to Chesapeake by exploring options for tickets in the afternoon.

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 October 12, 2025.

Travelers seeking maximum savings on their Orlando to Chesapeake flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday mornings 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 October 19, 2025.

The most flights from ORL to C6E are scheduled on a Monday (4 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 October 19, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

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
7,975 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

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
Spirit Airlines
6.3
Okay
8,102 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

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
3,133 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

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 Orlando to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Orlando to Chesapeake?

    A quick flight from Orlando to Chesapeake can take about 1h 57m. Spirit Airlines provides one of the quickest options available for as low as $100. Orlando and Chesapeake are separated by a distance of 655 mi. Generally, flights for this route are nonstop.

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

    The top 3 most reliable airlines when flying from Orlando to Chesapeake are Southwest (79%), JetBlue (76%) and Azul (75%).

  • What are the cheapest flights from Orlando to Chesapeake?

    While on average a flight from Orlando to Chesapeake is generally $134, our data shows the cheapest flight currently is $40. When looking at the most popular route, (Orlando - Norfolk), you can expect to pay $74 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 $38). Flying from Orlando to Chesapeake in June is currently the most expensive (average of $87). 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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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 October 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$48Average$129FlexibilityNo cancel feeOn-time65%
FrontierCheapest$71Average$134FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$76Average$111FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$85Average$210FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$87Average$279FlexibilityNo cancel feeOn-time63%
DeltaCheapest$88Average$261FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$162Average$330FlexibilityNo cancel feeOn-time71%

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