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Walt Disney World

$49+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 71 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 September 15, 2025.

Round-trip from

$85
(Kiwi.com)

One-way from

$49
(Breeze Airways)

Popular in

October

Cheapest in

May

Average price

$200
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. 20% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/175:38 pmORF - MCO
Nonstop2h 09mMultiple Airlines
Sun 10/197:00 amMCO - ORF
Nonstop2h 02mMultiple Airlines
Deal found 9/14$85
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:12 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Mon 10/62:39 pmMCO - ORF
Nonstop2h 00mMultiple Airlines
Deal found 9/13$90
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 9/145:47 pmORF - MCO
Nonstop2h 11mFrontier
Sun 9/212:50 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 9/14$91
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/25:12 pmORF - MCO
Nonstop2h 11mFrontier
Sun 10/52:50 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 9/13$92
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 9/215:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Sat 9/272:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Deal found 9/13$93
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 11/21:06 pmORF - MCO
Nonstop2h 10mFrontier
Sun 11/910:15 amMCO - ORF
Nonstop2h 01mFrontier
Deal found 9/13$94
This Frontier deal was found by Cheapflights users on 9/14. 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 9/255:12 pmORF - MCO
Nonstop2h 11mFrontier
Sun 9/282:50 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 9/14$97
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 10/315:38 pmORF - MCO
Nonstop2h 09mSpirit Airlines
Wed 11/510:00 pmMCO - ORF
Nonstop2h 07mSpirit Airlines
Deal found 9/14$99
This Priceline deal was found by Cheapflights users on 9/14. 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 10/124:14 pmORF - MCO
1 stop7h 58mFrontier
Sun 10/197:00 amMCO - ORF
Nonstop2h 02mFrontier
Deal found 9/14$106
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 9/215:47 pmORF - MCO
Nonstop2h 11mFrontier
Thu 9/256:00 amMCO - ORF
1 stop5h 24mFrontier
Deal found 9/15$109
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:12 pmORF - MCO
Nonstop2h 11mFrontier
Mon 10/66:00 amMCO - ORF
1 stop5h 24mFrontier
Deal found 9/13$110
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 11/135:27 pmORF - SFB
1 stop17h 39mMultiple Airlines
Thu 11/206:11 pmSFB - ORF
2 stops23h 25mMultiple Airlines
Deal found 9/14$315

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 September 15, 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 10/3

4:57 pm-7:12 pm

Nonstop2h 15m

Orlando

Fri 10/10

7:52 pm-10:02 pm

Nonstop2h 10m

$113

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 1/7

6:00 am-1:04 pm

1 stop7h 04m

Orlando

Thu 1/15

7:15 pm-11:30 pm

1 stop4h 15m

$130

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 10/7

11:24 am-5:11 pm

1 stop5h 47m

Orlando

Sat 10/11

4:30 pm-11:32 pm

1 stop7h 02m

$135

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/5

8:32 pm-10:42 pm

Nonstop2h 10m

Orlando

Mon 12/8

5:15 pm-10:43 pm

1 stop5h 28m

$137

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 10/7

11:15 am-1:20 pm

Nonstop2h 05m

Orlando

Sat 10/11

8:50 am-10:45 am

Nonstop1h 55m

$157

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/10

4:10 pm-6:15 pm

Nonstop2h 05m

Orlando

Wed 12/17

3:10 pm-10:00 pm

1 stop6h 50m

$163

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 10/14

2:55 pm-10:00 pm

1 stop7h 05m

Orlando

Tue 10/21

8:45 am-10:40 am

Nonstop1h 55m

$163

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 11/15

5:17 pm-11:30 pm

1 stop6h 13m

Orlando

Sat 11/22

1:58 pm-9:38 pm

1 stop7h 40m

$170

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 3/2

6:00 am-1:31 pm

1 stop7h 31m

Orlando

Fri 3/6

7:10 am-2:16 pm

1 stop7h 06m

$172

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 3/3

7:00 am-12:34 pm

1 stop5h 34m

Orlando

Wed 3/4

5:15 pm-10:55 pm

1 stop5h 40m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 30 results
1
2
3

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 September 12, 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 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 Walt Disney World?

Currently, May is the cheapest month in which you can book a flight from Chesapeake to Walt Disney World (average of $206). Flying from Chesapeake to Walt Disney World in November is currently the most expensive (average of $289). 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 September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Walt Disney World as you normally would.

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 September 14, 2025.

Travelers seeking maximum savings on their Chesapeake to Walt Disney World flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday 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 September 15, 2025.

The most flights from C6E to W9D are scheduled on a Saturday (4 on average). You will have fewer flight options on Monday, 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 Walt Disney World?

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 September 15, 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
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
699 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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 10m. Fly via Breeze Airways, United Airlines, or Spirit Airlines 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: Southwest (74%), Azul (67%), JetBlue( 66%).

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

    Looking at all options, your cheapest flight can be booked for $37. While the most popular route (Norfolk - Orlando) can be booked for $85 on average, our data indicates $149 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, May is the cheapest month in which you can book a flight from Chesapeake to Walt Disney World (average of $206). Flying from Chesapeake to Walt Disney World in November is currently the most expensive (average of $289). 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.

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$166FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$132FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$76Average$130FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$103Average$195FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$111Average$345FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$117Average$269FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$347FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$167Average$331FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$395FlexibilityNo cancel feeOn-time69%

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