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Chesapeake

$50+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chesapeake are usually found in May or November, booked 90 days in advance, depart on a Thursday or Saturday and return on a Thursday

Cheap 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 January 29, 2026.

This Priceline deal was found by Cheapflights users on 1/27. 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 2/187:50 pm
MCO
-
ORF
Nonstop2h 00m
Multiple Airlines
Sun 2/221:44 pm
ORF
-
MCO
Nonstop2h 16m
Multiple Airlines
Deal found 1/27$68
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/1312:26 pm
MCO
-
ORF
Nonstop2h 07m
Frontier
Sun 2/221:44 pm
ORF
-
MCO
Nonstop2h 16m
Frontier
Deal found 1/28$69
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2012:26 pm
MCO
-
ORF
Nonstop2h 07m
Frontier
Mon 2/238:49 am
ORF
-
MCO
Nonstop2h 13m
Frontier
Deal found 1/27$71
This Frontier deal was found by Cheapflights users on 1/27. 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.
Fri 2/2711:40 am
MCO
-
ORF
Nonstop2h 06m
Frontier
Mon 3/28:49 am
ORF
-
MCO
Nonstop2h 13m
Frontier
Deal found 1/27$72
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/197:50 pm
MCO
-
ORF
Nonstop2h 00m
Multiple Airlines
Sun 2/221:44 pm
ORF
-
MCO
Nonstop2h 16m
Multiple Airlines
Deal found 1/27$78
This Priceline deal was found by Cheapflights users on 1/28. 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.
Tue 2/2410:00 am
MCO
-
ORF
Nonstop2h 05m
Multiple Airlines
Wed 2/257:31 pm
ORF
-
MCO
1 stop4h 23m
Multiple Airlines
Deal found 1/28$79
This Frontier deal was found by Cheapflights users on 1/27. 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.
Thu 2/124:22 pm
MCO
-
ORF
Nonstop2h 06m
Frontier
Mon 2/161:42 pm
ORF
-
MCO
Nonstop2h 16m
Frontier
Deal found 1/27$80
This Frontier deal was found by Cheapflights users on 1/27. 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.
Tue 2/1010:00 am
MCO
-
ORF
Nonstop2h 05m
Frontier
Fri 2/133:18 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Deal found 1/27$84
This Frontier deal was found by Cheapflights users on 1/27. 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.
Sat 3/2812:24 pm
MCO
-
ORF
Nonstop2h 07m
Frontier
Wed 4/13:28 pm
ORF
-
MCO
Nonstop2h 10m
Frontier
Deal found 1/27$85
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 3/2812:24 pm
MCO
-
ORF
Nonstop2h 07m
Multiple Airlines
Tue 3/316:45 am
ORF
-
MCO
Nonstop2h 06m
Multiple Airlines
Deal found 1/27$86
This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/317:50 pm
MCO
-
ORF
Nonstop2h 00m
Spirit Airlines
Sun 2/16:45 am
ORF
-
MCO
Nonstop2h 12m
Spirit Airlines
Deal found 1/28$87

Find flight deals from Orlando to Chesapeake

Keep the following information in mind while searching for Orlando to Chesapeake flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$68
(Priceline)

One-way from

$50
(Kiwi.com)

Popular in

April

Cheapest in

May

Average price

$189
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. 12% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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 2/20

12:26 pm-2:33 pm

Nonstop2h 07m

Norfolk

Sun 2/22

1:44 pm-4:00 pm

Nonstop2h 16m

$68

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 2/13

12:26 pm-2:33 pm

Nonstop2h 07m

Norfolk

Sun 2/22

1:44 pm-4:00 pm

Nonstop2h 16m

$69

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 2/19

7:50 pm-9:50 pm

Nonstop2h 00m

Norfolk

Sun 2/22

1:44 pm-4:00 pm

Nonstop2h 16m

$78

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 2/27

11:40 am-1:46 pm

Nonstop2h 06m

Norfolk

Fri 3/6

3:26 pm-5:41 pm

Nonstop2h 15m

$79

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Wed 3/11

7:50 pm-9:50 pm

Nonstop2h 00m

Norfolk

Sat 3/21

3:26 pm-5:41 pm

Nonstop2h 15m

$85

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 2/7

7:50 pm-9:50 pm

Nonstop2h 00m

Norfolk

Mon 2/9

6:45 am-8:57 am

Nonstop2h 12m

$98

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 4/18

2:54 pm-4:53 pm

Nonstop1h 59m

Norfolk

Mon 4/20

5:48 pm-8:04 pm

Nonstop2h 16m

$101

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 2/19

7:50 pm-9:50 pm

Nonstop2h 00m

Norfolk

Mon 2/23

7:31 pm-7:39 am

1 stop12h 08m

$106

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 2/20

12:26 pm-2:33 pm

Nonstop2h 07m

Norfolk

Sun 2/22

7:31 pm-11:54 pm

1 stop4h 23m

$112

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Tue 3/24

8:34 pm-10:32 pm

Nonstop1h 58m

Norfolk

Fri 3/27

6:45 am-8:51 am

Nonstop2h 06m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 22 results
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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 January 23, 2026.

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, July is the cheapest month in which you can book a flight from Orlando to Chesapeake (average of $43). 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 January 29, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 15% 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 January 24, 2026.

Travelers seeking maximum savings on their Orlando to Chesapeake flight should consider departing on Monday mornings when fares are most often at their lowest. Monday 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 January 29, 2026.

The most flights from ORL to C6E are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, 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 January 29, 2026.
Get a feel of what it's like to fly with Breeze Airways, Southwest, 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.
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Food

6.7

Overall

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Food

6.7

Overall

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,267 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Food

6.7

Overall

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,204 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Food

6.7

Overall

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Spirit Airlines
6.3
Okay
8,389 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Food

6.7

Overall

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,056 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Food

6.7

Overall

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 2h 07m. Frontier provides one of the quickest options available for as low as $68. Orlando and Chesapeake are separated by a distance of 655 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Orlando to Chesapeake one-way?

    $30 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Allegiant Air, with prices starting from $42 and $45, respectively.

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

    The top 3 most reliable airlines when flying from Orlando to Chesapeake are Azul (87%), JetBlue (79%) and Spirit Airlines (75%).

  • What are the cheapest flights from Orlando to Chesapeake?

    While on average a flight from Orlando to Chesapeake is generally $129, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Orlando - Norfolk), you can expect to pay $63 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, July is the cheapest month in which you can book a flight from Orlando to Chesapeake (average of $43). 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.

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 8 airlines flying from Orlando to Chesapeake

Discover the top 8 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$40Average$110FlexibilityNo cancel feeOn-time65%
FrontierCheapest$46Average$104FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$76Average$109FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$78Average$192FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$79Average$265FlexibilityNo cancel feeOn-time63%
DeltaCheapest$88Average$283FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$103Average$135FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$162Average$306FlexibilityNo cancel feeOn-time71%

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