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$40+ Cheap flights from Chesapeake, VA to Orlando (ORL)

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or March, booked 87 days in advance, depart on a Thursday or Monday and return on a Thursday

Cheap flight deals from Chesapeake to Orlando

Cheapest flights from Chesapeake to Orlando
Explore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/319:10 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Sat 2/281:46 pm
MCO
-
ORF
Nonstop2h 06m
Frontier
Deal found 1/27$74
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/213:26 pm
ORF
-
MCO
Nonstop2h 15m
Multiple Airlines
Wed 3/258:34 pm
MCO
-
ORF
Nonstop1h 58m
Multiple Airlines
Deal found 1/27$75
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.
Sat 2/79:10 pm
ORF
-
MCO
Nonstop2h 15m
Multiple Airlines
Wed 2/113:19 pm
MCO
-
ORF
Nonstop2h 01m
Multiple Airlines
Deal found 1/28$76
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
-
MCO
1 stop4h 23m
Spirit Airlines
Wed 3/47:50 pm
MCO
-
ORF
Nonstop2h 00m
Spirit Airlines
Deal found 1/28$77
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1412:29 pm
ORF
-
MCO
Nonstop2h 15m
Multiple Airlines
Wed 2/187:50 pm
MCO
-
ORF
Nonstop2h 00m
Multiple Airlines
Deal found 1/27$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.
Sat 2/79:10 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Tue 2/1010:00 am
MCO
-
ORF
Nonstop2h 05m
Frontier
Deal found 1/27$80
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:45 am
ORF
-
MCO
Nonstop2h 12m
Spirit Airlines
Fri 2/207:50 pm
MCO
-
ORF
Nonstop2h 00m
Spirit Airlines
Deal found 1/28$81
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/54:01 pm
ORF
-
MCO
Nonstop2h 16m
Frontier
Thu 2/124:22 pm
MCO
-
ORF
Nonstop2h 06m
Frontier
Deal found 1/28$82
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 3/143:26 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Sat 3/2112:24 pm
MCO
-
ORF
Nonstop2h 07m
Frontier
Deal found 1/28$84
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:45 am
ORF
-
MCO
Nonstop2h 12m
Spirit Airlines
Sat 2/282:50 pm
MCO
-
ORF
1 stop4h 59m
Spirit Airlines
Deal found 1/28$85
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.
Mon 2/96:45 am
ORF
-
MCO
Nonstop2h 12m
Multiple Airlines
Thu 2/124:22 pm
MCO
-
ORF
Nonstop2h 06m
Multiple Airlines
Deal found 1/28$86
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 1/3110:31 pm
ORF
-
SFB
1 stop24h 53m
Multiple Airlines
Mon 2/28:00 am
SFB
-
ORF
2 stops34h 38m
Multiple Airlines
Deal found 1/27$394

Find flight deals from Chesapeake to Orlando

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$75
(CheapOair)

One-way from

$40
(Super.com)

Popular in

November

Cheapest in

May

Average price

$190
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
Search Deals
From Chesapeake to Orlando (ORL)
Search Deals
One-way flight from Chesapeake to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($8 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 Chesapeake to Orlando 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 Chesapeake to Orlando that are best for you.

Fly from

Chesapeake

Fly to

Orlando

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/25

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

Wed 3/4

6:00 am-6:26 pm

1 stop12h 26m

$125

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 3/27

8:41 pm-7:39 am

1 stop10h 58m

Orlando

Tue 3/31

8:34 pm-10:32 pm

Nonstop1h 58m

$154

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 2/20

7:31 pm-7:39 am

1 stop12h 08m

Orlando

Sat 2/28

6:00 am-7:49 pm

1 stop13h 49m

$158

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 3/14

8:41 pm-7:39 am

1 stop10h 58m

Orlando

Sat 3/21

10:30 am-7:46 pm

1 stop9h 16m

$171

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 2/20

6:45 am-8:57 am

Nonstop2h 12m

Orlando

Sun 2/22

10:52 am-12:57 pm

Nonstop2h 05m

$201

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/25

12:30 pm-6:35 pm

1 stop6h 05m

Orlando

Wed 3/4

12:55 pm-9:50 pm

2 stops8h 55m

$212

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/11

7:00 am-11:59 pm

2 stops16h 59m

Orlando

Thu 3/5

7:50 pm-9:50 pm

Nonstop2h 00m

$221

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 2/23

11:50 am-10:00 pm

2 stops10h 10m

Orlando

Fri 2/27

9:45 am-2:25 pm

1 stop4h 40m

$222

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 3/9

2:50 pm-8:45 pm

1 stop5h 55m

Orlando

Wed 3/11

3:40 pm-10:35 pm

2 stops6h 55m

$242

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Wed 2/11

10:31 pm-10:18 pm

1 stop23h 47m

Orlando Sanford Intl

Mon 2/16

10:45 am-6:26 pm

2 stops31h 41m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 29 results
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Best time to book a flight from Chesapeake to Orlando

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Orlando. Price data was last updated on January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 87 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 Chesapeake to Orlando?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $43). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $84). 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 C6E to ORL?

Find hourly flight availability from Chesapeake to Orlando. 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.

It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chesapeake to Orlando?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Orlando. Price data was last updated on January 24, 2026.

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

Weekly flight availability from Chesapeake to Orlando

Explore weekly flight availability from Chesapeake to Orlando. 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 C6E to ORL 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 (1 on average).

How much does it cost to fly round-trip from Chesapeake to Orlando?

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. 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 Orlando. Reviews last updated January 29, 2026.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, and American Airlines from Chesapeake to Orlando to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

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

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

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

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

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

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

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

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

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

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

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 Chesapeake to Orlando. 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 Chesapeake to Orlando?

    There are many flights that can get you from Chesapeake to Orlando in 4h 23m. Fly via Spirit Airlines to get the fastest option. There are 655 mi between Chesapeake and Orlando.

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

    One-way options have recently been found by users for as low as $36 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $40 and Breeze Airways from $49 one-way.

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

    The top 3 most reliable airlines when flying from Chesapeake to Orlando are Azul (83%), JetBlue (83%) and Southwest (72%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $47. On average you can expect to pay $243. The most popular route, (Norfolk - Orlando), can usually be booked for $54.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $43). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $84). 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 Chesapeake to Orlando

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Chesapeake to Orlando

Discover the top 9 airlines that operate flights from Chesapeake to Orlando. 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$41Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$156FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$78Average$166FlexibilityNo cancel feeOn-time88%
DeltaCheapest$88Average$343FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$89Average$224FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$100Average$295FlexibilityNo cancel feeOn-time63%
Breeze AirwaysCheapest$100Average$246FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$138Average$437FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$163Average$337FlexibilityNo cancel feeOn-time71%

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