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$39+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or March, booked 71 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$95
(Priceline)

One-way from

$39
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$199
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. 15% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 23, 2025.

This Priceline deal was found by Cheapflights users on 10/22. 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 11/209:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Sun 11/236:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/22$95
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/88:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Thu 12/185:15 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 10/22$96
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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.
Wed 11/56:33 pmORF - MCO
Nonstop2h 11mSpirit Airlines
Fri 11/710:27 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 10/21$99
This CheapOair deal was found by Cheapflights users on 10/23. 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.
Tue 11/116:33 pmORF - MCO
Nonstop2h 11mSpirit Airlines
Sat 11/156:30 amMCO - ORF
1 stop10h 27mSpirit Airlines
Deal found 10/23$104
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 11/86:02 pmORF - MCO
1 stop4h 06mSpirit Airlines
Wed 11/123:40 pmMCO - ORF
Nonstop1h 58mSpirit Airlines
Deal found 10/21$105
This Priceline deal was found by Cheapflights users on 10/21. 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 11/144:57 pmORF - MCO
Nonstop2h 15mMultiple Airlines
Mon 11/1710:27 amMCO - ORF
Nonstop1h 57mMultiple Airlines
Deal found 10/21$106
This Priceline deal was found by Cheapflights users on 10/21. 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 11/91:11 pmORF - MCO
Nonstop2h 10mFrontier
Thu 11/135:25 amMCO - ORF
1 stop9h 00mFrontier
Deal found 10/21$109
This CheapOair deal was found by Cheapflights users on 10/21. 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.
Wed 11/269:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Mon 12/16:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/21$110
This Priceline deal was found by Cheapflights users on 10/22. 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 11/2611:33 amORF - MCO
Nonstop2h 12mFrontier
Mon 12/17:40 amMCO - ORF
Nonstop2h 03mFrontier
Deal found 10/22$113
This Priceline deal was found by Cheapflights users on 10/21. 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 11/133:20 pmORF - MCO
1 stop5h 46mMultiple Airlines
Mon 11/1710:27 amMCO - ORF
Nonstop1h 57mMultiple Airlines
Deal found 10/21$115
This Mytrip deal was found by Cheapflights users on 10/23. 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.
Wed 11/126:33 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Fri 11/145:25 amMCO - ORF
1 stop5h 23mMultiple Airlines
Deal found 10/23$118
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/69:39 pmORF - SFB
1 stop16h 47mMultiple Airlines
Sat 12/134:37 pmSFB - ORF
1 stop22h 12mMultiple Airlines
Deal found 10/22$274

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 October 23, 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

Sun 1/11

8:32 pm-10:42 pm

Nonstop2h 10m

Orlando

Fri 1/16

5:30 pm-7:37 pm

Nonstop2h 07m

$124

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/17

1:56 pm-4:11 pm

Nonstop2h 15m

Orlando

Wed 12/24

10:00 am-12:10 pm

Nonstop2h 10m

$143

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/10

4:10 pm-6:15 pm

Nonstop2h 05m

Orlando

Tue 12/16

9:20 am-4:45 pm

1 stop7h 25m

$151

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/12

7:39 pm-12:50 am

1 stop5h 11m

Orlando

Mon 12/15

9:00 am-2:09 pm

1 stop5h 09m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/17

12:15 pm-5:10 pm

1 stop4h 55m

Orlando

Wed 12/24

2:45 pm-9:05 pm

1 stop6h 20m

$196

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 11/11

4:10 pm-6:15 pm

Nonstop2h 05m

Orlando

Sat 11/15

8:55 am-10:50 am

Nonstop1h 55m

$199

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 11/12

7:53 pm-8:15 am

1 stop12h 22m

Orlando

Fri 11/14

6:05 pm-4:57 pm

3 stops22h 52m

$215

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 11/8

3:15 pm-9:54 pm

1 stop6h 39m

Orlando

Wed 11/12

6:00 am-9:33 am

1 stop3h 33m

$219

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/11

12:38 pm-4:25 pm

1 stop3h 47m

Orlando

Mon 12/15

9:10 am-11:20 am

Nonstop2h 10m

$222

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 1/9

8:09 pm-11:59 pm

2 stops27h 50m

Orlando

Mon 1/12

6:55 am-7:14 pm

1 stop12h 19m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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 17, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 71 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 $40). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $86). 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 October 23, 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 October 19, 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. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 23, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, 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.
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

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
Delta
7.9
Good
7,982 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

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
11,032 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

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
8,103 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

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
3,128 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

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 05m. Fly via Spirit Airlines, Breeze Airways, or Southwest 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 $54 on Breeze Airways. Other airlines that offer cheap prices include Spirit Airlines from $55 and Southwest from $55 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 Southwest (84%), JetBlue (72%) and Azul (72%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $40. On average you can expect to pay $179. 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 $40). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $86). 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$170FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$161FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$137FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$101Average$259FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$106Average$309FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$117Average$269FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$327FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$414FlexibilityNo cancel feeOn-time69%

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