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$48+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Dec 7 — Dec 141
Sun 12/7
Sun 12/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or March, booked 40 days in advance, depart on a Monday or Thursday and return on a Thursday

Cheap flight deals from Chesapeake to Orlando

Keep the following information in mind while searching for Chesapeake to Orlando flight deals. Data was last updated November 7, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$94
(Kiwi.com)

One-way from

$48
(Super.com)

Popular in

December

Cheapest in

May

Average price

$245
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
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From Chesapeake to Orlando (ORL)
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One-way flight from Chesapeake to Orlando (ORL)
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Highest demand for flights based on searches. 13% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 7, 2025.

This Expedia deal was found by Cheapflights users on 11/7. 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.
Mon 12/155:40 pmORF - MCO
1 stop6h 41mMultiple Airlines
Wed 12/244:40 pmMCO - ORF
Nonstop2h 05mMultiple Airlines
Deal found 11/7$95
This Super.com deal was found by Cheapflights users on 11/7. 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.
Thu 11/139:03 pmORF - MCO
Nonstop2h 07mSpirit Airlines
Fri 11/1410:27 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/7$96
This CheapOair deal was found by Cheapflights users on 11/6. 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.
Thu 11/201:09 pmORF - MCO
1 stop11h 31mFrontier
Sun 11/2311:14 amMCO - ORF
Nonstop2h 01mFrontier
Deal found 11/6$98
This Super.com deal was found by Cheapflights users on 11/7. 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.
Fri 12/58:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Fri 12/125:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/7$99
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Thu 12/115:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/6$100
This Super.com deal was found by Cheapflights users on 11/6. 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.
Thu 11/139:03 pmORF - MCO
Nonstop2h 07mSpirit Airlines
Thu 11/206:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 11/6$103
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/229:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Tue 11/256:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 11/5$104
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 11/277:18 pmORF - MCO
1 stop4h 07mSpirit Airlines
Thu 12/45:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/6$105
This Priceline deal was found by Cheapflights users on 11/5. 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 11/132:00 pmORF - MCO
Nonstop2h 09mMultiple Airlines
Fri 11/147:52 pmMCO - ORF
Nonstop2h 10mMultiple Airlines
Deal found 11/5$107
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 11/232:10 pmORF - MCO
Nonstop2h 15mMultiple Airlines
Tue 11/256:32 pmMCO - ORF
Nonstop1h 59mMultiple Airlines
Deal found 11/5$110
This Priceline deal was found by Cheapflights users on 11/6. 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 12/512:00 pmORF - MCO
1 stop5h 27mMultiple Airlines
Mon 12/85:46 amMCO - ORF
Nonstop1h 57mMultiple Airlines
Deal found 11/6$113
This Priceline deal was found by Cheapflights users on 11/5. 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 12/48:38 amORF - MCO
Nonstop2h 12mMultiple Airlines
Thu 12/1110:02 amMCO - ORF
1 stop6h 45mMultiple Airlines
Deal found 11/5$114

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 November 7, 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

Fri 12/12

12:00 pm-5:27 pm

1 stop5h 27m

Orlando

Mon 12/15

5:46 am-7:43 am

Nonstop1h 57m

$113

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/5

12:00 pm-5:27 pm

1 stop5h 27m

Orlando

Mon 12/8

5:46 am-7:43 am

Nonstop1h 57m

$113

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 11/17

1:19 pm-3:30 pm

Nonstop2h 11m

Orlando

Tue 11/18

3:40 pm-5:38 pm

Nonstop1h 58m

$123

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 2/5

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

Tue 2/10

10:13 am-12:15 pm

Nonstop2h 02m

$127

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 2/5

1:10 pm-3:28 pm

Nonstop2h 18m

Orlando

Sun 2/8

5:45 am-10:41 am

1 stop4h 56m

$136

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 12/23

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

Mon 12/29

4:40 pm-6:45 pm

Nonstop2h 05m

$139

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 11/17

1:19 pm-3:30 pm

Nonstop2h 11m

Orlando

Mon 11/17

7:52 pm-10:02 pm

Nonstop2h 10m

$147

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 12/9

4:10 pm-6:15 pm

Nonstop2h 05m

Orlando

Thu 12/11

1:40 pm-3:30 pm

Nonstop1h 50m

$153

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/6

11:30 am-4:35 pm

1 stop5h 05m

Orlando

Sat 12/13

8:55 am-10:50 am

Nonstop1h 55m

$163

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/12

8:11 pm-5:55 pm

2 stops21h 44m

Orlando

Mon 12/15

5:46 am-7:43 am

Nonstop1h 57m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/7

Showing 1-10 of 41 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 October 31, 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 $41). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $85). 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 November 7, 2025.

It’s typically best to fly out from Chesapeake to Orlando in the evening. Doing so could potentially save you 23% 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 November 2, 2025.

Travelers seeking maximum savings on their Chesapeake to Orlando flight should consider departing on Tuesday evenings 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 November 7, 2025.

The most flights from C6E to ORL are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 November 7, 2025.
Peruse reviews from past customers who have flown with Southwest, American Airlines, and Allegiant Air 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.
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
11,044 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
Allegiant Air
7.2
Good
698 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
8,127 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
3,115 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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 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 11m. 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 most reliable airlines from Chesapeake to Orlando?

    The top 3 most reliable airlines when flying from Chesapeake to Orlando are JetBlue (87%), Southwest (85%) and Azul (83%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $39. On average you can expect to pay $171. The most popular route, (Norfolk - Orlando), can usually be booked for $59.

  • 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 $41). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $85). 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 November 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$172FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$161FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$133FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$103Average$309FlexibilityNo cancel feeOn-time63%
Breeze AirwaysCheapest$109Average$266FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$117Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$345FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$329FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$432FlexibilityNo cancel feeOn-time69%

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