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Walt Disney World

$48+ Cheap flights from Chesapeake, VA to Bay Lake, FL

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 — MCO
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Walt Disney World 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 Walt Disney World

Keep the following information in mind while searching for Chesapeake to Walt Disney World flight deals. Data was last updated November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$95
(Priceline)

One-way from

$48
(Kiwi.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 Walt Disney World
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One-way flight from Chesapeake to Walt Disney World
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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 Walt Disney World

Cheapest flights from Chesapeake to Walt Disney World
Explore the most affordable flight options available from Chesapeake to Walt Disney World. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

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 Frontier 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 Frontier 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
Mon 11/247:40 amMCO - ORF
Nonstop2h 03mFrontier
Deal found 11/5$99
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/309:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Fri 12/55:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/5$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 Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:26 pmORF - MCO
Nonstop2h 03mMultiple Airlines
Sun 11/2311:14 amMCO - ORF
Nonstop2h 01mMultiple 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 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.
Fri 12/58:38 amORF - MCO
Nonstop2h 12mMultiple Airlines
Fri 12/125:30 amMCO - ORF
1 stop5h 30mMultiple Airlines
Deal found 11/5$109
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:19 pmORF - MCO
Nonstop2h 11mSpirit Airlines
Sat 11/226:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 11/5$110
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 11/309:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Thu 12/45:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/5$111
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 Walt Disney World 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 6, 2025.
Use the filters below to find and compare flights from Chesapeake to Bay Lake that are best for you.

Fly from

Chesapeake

Fly to

Walt Disney World

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 2/6

4:15 pm-6:30 pm

Nonstop2h 15m

Orlando

Mon 2/9

9:15 am-11:10 am

Nonstop1h 55m

$117

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/6

5:45 pm-7:50 pm

Nonstop2h 05m

Orlando

Sat 12/13

8:55 am-10:50 am

Nonstop1h 55m

$153

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/5

7:55 am-10:10 am

Nonstop2h 15m

Orlando

Mon 12/15

9:10 am-11:20 am

Nonstop2h 10m

$168

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 1/8

7:00 am-2:41 pm

1 stop7h 41m

Orlando

Sat 1/10

1:11 pm-8:44 pm

1 stop7h 33m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/11

6:03 pm-12:50 am

1 stop6h 47m

Orlando

Mon 12/15

5:30 am-11:32 am

1 stop6h 02m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/6

2:31 pm-9:47 pm

1 stop7h 16m

Orlando

Mon 12/15

5:30 am-11:32 am

1 stop6h 02m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 1/22

7:00 am-2:41 pm

1 stop7h 41m

Orlando

Sun 1/25

6:15 am-11:20 am

1 stop5h 05m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 1/23

6:00 am-12:42 pm

1 stop6h 42m

Orlando

Tue 1/27

1:10 pm-5:05 pm

1 stop3h 55m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 12/22

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

Fri 12/26

4:40 pm-6:45 pm

Nonstop2h 05m

$179

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Sat 12/6

9:39 pm-2:26 pm

1 stop16h 47m

Orlando Sanford Intl

Sat 12/13

4:37 pm-2:49 pm

1 stop22h 12m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 35 results
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Best time to book a flight from Chesapeake to Walt Disney World

Have a flexible travel schedule? Discover the best time to fly to Walt Disney World 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 Bay Lake

How far ahead should I book a flight from Chesapeake to Walt Disney World?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Walt Disney World. Price data was last updated on October 31, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Walt Disney World, 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 Walt Disney World?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to Walt Disney World (average of $41). Flying from Chesapeake to Walt Disney World 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 W9D?

Find hourly flight availability from Chesapeake to Walt Disney World. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Chesapeake to Walt Disney World in the evening. If you’re flexible enough to do this you can expect to save up to 4% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chesapeake to Walt Disney World?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Walt Disney World. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Chesapeake to Walt Disney World 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 Walt Disney World

Explore weekly flight availability from Chesapeake to Walt Disney World. 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 6, 2025.

The most flights from C6E to W9D are scheduled on a Monday (8 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 Walt Disney World

Get insights into the airlines that provide service to Walt Disney World. 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 Walt Disney World. Reviews last updated November 6, 2025.
Peruse reviews from past customers who have flown with Southwest, American Airlines, and Allegiant Air from Chesapeake to Bay Lake 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
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
697 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
8,115 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
3,116 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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 Walt Disney World. 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 Walt Disney World?

    There are many flights that can get you from Chesapeake to Walt Disney World in 2h 15m. Fly via Southwest, Breeze Airways, or Delta to get the fastest option. Chesapeake and Walt Disney World are separated by a distance of 655 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most reliable airlines from Chesapeake to Walt Disney World?

    Before booking your flight to Walt Disney World from Chesapeake, check out the most reliable airlines to get you to your destination on time: JetBlue (87%), Southwest (85%), Azul( 83%).

  • What are the cheapest flights from Chesapeake to Walt Disney World?

    Looking at all options, your cheapest flight can be booked for $39. While the most popular route (Norfolk - Orlando) can be booked for $58 on average, our data indicates $171 when flying from Chesapeake to Walt Disney World.

  • Can I find deals for flights from Chesapeake to Walt Disney World that include hotel bookings?

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

  • How can I find direct flights from Chesapeake to Walt Disney World?

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

  • Can I find deals for business class flights from Chesapeake to Walt Disney World?

    Yes. Cheapflights offers flight deals from Chesapeake to Walt Disney World 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 Walt Disney World?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to Walt Disney World (average of $41). Flying from Chesapeake to Walt Disney World 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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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 Walt Disney World

Discover the top 9 airlines that operate flights from Chesapeake to Walt Disney World. 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 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$169FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$145FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$75Average$131FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$103Average$219FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$103Average$343FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$117Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$349FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$343FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$445FlexibilityNo cancel feeOn-time69%

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