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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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or January, booked 40 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 December 12, 2025.

This Super.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/307:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Fri 1/97:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 12/10$88
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/307:40 pmORF - MCO
Nonstop2h 18mMultiple Airlines
Wed 1/75:20 amMCO - ORF
1 stop5h 25mMultiple Airlines
Deal found 12/10$121
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/207:40 pmORF - MCO
Nonstop2h 18mMultiple Airlines
Tue 12/2312:14 pmMCO - ORF
Nonstop2h 02mMultiple Airlines
Deal found 12/10$122
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/233:11 pmORF - MCO
Nonstop2h 16mMultiple Airlines
Tue 12/304:40 pmMCO - ORF
Nonstop2h 05mMultiple Airlines
Deal found 12/10$126
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/233:11 pmORF - MCO
Nonstop2h 16mMultiple Airlines
Tue 1/64:40 pmMCO - ORF
Nonstop2h 05mMultiple Airlines
Deal found 12/10$127
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/227:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Tue 1/64:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/10$128
This Priceline deal was found by Cheapflights users on 12/10. 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.
Sun 12/217:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Thu 12/254:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/10$135
This Frontier deal was found by Cheapflights users on 12/10. 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 12/233:11 pmORF - MCO
Nonstop2h 16mFrontier
Wed 12/315:15 amMCO - ORF
1 stop5h 17mFrontier
Deal found 12/10$136
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Wed 12/243:01 pmORF - MCO
1 stop16h 44mSpirit Airlines
Tue 1/64:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/10$138
This Super.com deal was found by Cheapflights users on 12/10. 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 12/207:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Mon 12/224:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/10$139
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/207:40 pmORF - MCO
Nonstop2h 18mMultiple Airlines
Sun 12/2112:12 pmMCO - ORF
Nonstop2h 02mMultiple Airlines
Deal found 12/10$141
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/227:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Tue 12/304:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/10$149

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 December 12, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$80
(Super.com)

One-way from

$40
(Frontier)

Popular in

November

Cheapest in

May

Average price

$207
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. 18% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 12, 2025.
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

Sat 1/17

6:45 am-8:57 am

Nonstop2h 12m

Orlando

Wed 1/21

4:26 pm-6:25 pm

Nonstop1h 59m

$80

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 2/21

12:29 pm-2:44 pm

Nonstop2h 15m

Orlando

Sat 2/28

1:46 pm-3:52 pm

Nonstop2h 06m

$80

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 1/30

6:45 am-8:57 am

Nonstop2h 12m

Orlando

Sat 1/31

7:50 pm-9:50 pm

Nonstop2h 00m

$80

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/18

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

Tue 2/24

10:00 am-12:05 pm

Nonstop2h 05m

$100

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 1/30

11:43 am-7:54 pm

1 stop8h 11m

Orlando

Sat 1/31

6:10 pm-8:15 pm

Nonstop2h 05m

$104

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 1/7

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

Mon 1/12

5:20 am-10:45 am

1 stop5h 25m

$121

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 2/21

6:45 am-8:57 am

Nonstop2h 12m

Orlando

Sat 2/28

2:50 pm-7:39 pm

1 stop4h 49m

$127

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 2/8

7:33 pm-6:00 pm

2 stops22h 27m

Orlando

Fri 2/13

7:50 pm-9:50 pm

Nonstop2h 00m

$173

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/18

4:00 pm-6:10 pm

Nonstop2h 10m

Orlando

Tue 2/24

1:25 pm-3:25 pm

Nonstop2h 00m

$197

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 1/19

7:33 pm-9:59 am

3 stops38h 26m

Orlando

Fri 1/23

6:00 am-6:38 pm

1 stop12h 38m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 37 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 December 5, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 40 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 $42). Flying from Chesapeake to Orlando in June is currently the most expensive (average of $83). 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 December 12, 2025.

It’s typically best to fly out from Chesapeake to Orlando in the evening. Doing so could potentially save you 17% on the flight price compared to flying in the morning, 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 December 6, 2025.

Travelers seeking maximum savings on their Chesapeake to Orlando flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Tuesday at noon 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 December 12, 2025.

The most flights from C6E to ORL are scheduled on a Thursday (9 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 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 December 12, 2025.
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
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Breeze Airways
8.2
Very good
244 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Southwest
7.9
Good
4,253 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
American Airlines
7.2
Good
11,050 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Spirit Airlines
6.3
Okay
8,180 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Frontier
5.8
Fair
3,084 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

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 2h 12m. Fly via Spirit Airlines or Frontier to get the fastest option. There are 655 mi between Chesapeake and Orlando. Generally, flights for this route are nonstop.

  • 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 $37 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $39 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 JetBlue (86%), Southwest (86%) and Azul (79%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $38. On average you can expect to pay $158. The most popular route, (Norfolk - Orlando), can usually be booked for $58.

  • 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 $42). Flying from Chesapeake to Orlando in June is currently the most expensive (average of $83). 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$160FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$163FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$133FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$100Average$302FlexibilityNo cancel feeOn-time63%
Breeze AirwaysCheapest$113Average$265FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$116Average$239FlexibilityNo cancel feeOn-time62%
DeltaCheapest$129Average$363FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$325FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$427FlexibilityNo cancel feeOn-time69%

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