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Walt Disney World

$49+ Cheap flights from Midway (MDW) 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Walt Disney World are usually found in August or July, booked 62 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap flight deals from Midway to Walt Disney World

Keep the following information in mind while searching for Midway to Walt Disney World flight deals. Data was last updated September 15, 2025.

Round-trip from

$99
(Cheapflightsfares)

One-way from

$49
(Kiwi.com)

Popular in

September

Cheapest in

August

Average price

$371
From Chicago Midway to Walt Disney World
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One-way flight from Chicago Midway to Walt Disney World
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Highest demand for flights based on searches. 1% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% 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 Midway to Walt Disney World

Cheapest flights from Midway to Walt Disney World
Explore the most affordable flight options available from Midway to Walt Disney World. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

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.
Sat 10/411:21 amMDW - MCO
Nonstop2h 43mFrontier
Mon 10/65:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 9/14$99
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:19 amMDW - MCO
Nonstop2h 41mFrontier
Sun 10/57:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/13$100
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 9/269:48 amMDW - MCO
Nonstop2h 40mFrontier
Sun 9/287:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/14$102
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:19 amMDW - MCO
Nonstop2h 41mFrontier
Fri 10/37:00 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/13$103
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:48 amMDW - MCO
Nonstop2h 40mFrontier
Mon 9/295:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 9/13$104
This Frontier deal was found by Cheapflights users on 9/12. 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.
Fri 11/73:47 pmMDW - MCO
1 stop6h 50mFrontier
Sat 11/88:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/12$109
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 10/1912:09 pmMDW - MCO
Nonstop2h 42mFrontier
Thu 10/237:50 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/13$110
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.
Mon 10/135:28 pmMDW - MCO
Nonstop2h 42mFrontier
Thu 10/168:50 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/15$111
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:49 amMDW - MCO
Nonstop2h 38mFrontier
Thu 12/411:10 amMCO - MDW
Nonstop3h 00mFrontier
Deal found 9/13$112
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/206:24 pmMDW - MCO
1 stop10h 40mFrontier
Sat 10/258:25 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/13$113
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:49 amMDW - MCO
Nonstop2h 40mFrontier
Sat 10/254:35 pmMCO - MDW
1 stop7h 45mFrontier
Deal found 9/13$114
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1112:30 pmMDW - MCO
1 stop8h 50mFrontier
Sun 10/129:44 amMCO - MDW
Nonstop2h 55mFrontier
Deal found 9/15$115

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 Chicago Midway Airport to Bay Lake that are best for you.

Fly from

Midway

Fly to

Walt Disney World

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 9/28

6:30 am-3:07 pm

1 stop7h 37m

Orlando

Sun 10/5

7:25 am-9:18 am

Nonstop2h 53m

$150

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/14

11:40 am-3:10 pm

Nonstop2h 30m

Orlando

Thu 10/16

7:30 pm-9:15 pm

Nonstop2h 45m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/13

8:45 pm-12:15 am

Nonstop2h 30m

Orlando

Wed 10/15

2:55 pm-4:40 pm

Nonstop2h 45m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 10/19

8:55 pm-12:30 am

Nonstop2h 35m

Orlando

Wed 10/22

2:55 pm-4:40 pm

Nonstop2h 45m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 12/3

5:05 am-8:40 am

Nonstop2h 35m

Orlando

Wed 12/10

4:35 pm-6:25 pm

Nonstop2h 50m

$179

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 12/6

12:30 pm-6:35 pm

1 stop5h 05m

Orlando

Sat 12/13

7:05 am-8:55 am

Nonstop2h 50m

$183

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/14

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Tue 10/21

6:20 pm-10:25 pm

1 stop5h 05m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/6

7:05 am-10:35 am

Nonstop2h 30m

Orlando

Mon 10/13

6:35 am-8:20 am

Nonstop2h 45m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 11/24

7:35 pm-11:10 pm

Nonstop2h 35m

Orlando

Fri 11/28

6:10 am-9:55 am

1 stop4h 45m

$204

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 12/10

2:25 pm-7:15 pm

1 stop3h 50m

Orlando

Tue 12/16

9:20 am-12:45 pm

1 stop4h 25m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 34 results
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Best time to book a flight from Midway to Walt Disney World

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

How far ahead should I book a flight from Chicago Midway Airport to Walt Disney World?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Walt Disney World. Price data was last updated on September 12, 2025.

The best time to book flights from Chicago Midway Airport to Walt Disney World is 62 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to Walt Disney World?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $206). Flying from Chicago Midway Airport 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 MDW to W9D?

Find hourly flight availability from Midway 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.

When flying from Chicago Midway Airport to Walt Disney World, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago Midway Airport to Walt Disney World?

Use this chart to determine the cheapest time to fly round-trip from Midway to Walt Disney World. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Walt Disney World flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago Midway Airport to Walt Disney World

Explore weekly flight availability from Midway 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 MDW to W9D are scheduled on a Monday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 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 September 15, 2025.
Read reviews from past customers who have flown Southwest and Frontier from Chicago Midway Airport to Bay Lake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Chicago Midway Airport to Walt Disney World?

    There are many flights that can get you from Chicago Midway Airport to Walt Disney World in 2h 30m. Fly via Frontier, Southwest, or Allegiant Air to get the fastest option. The distance between Chicago Midway Airport and Walt Disney World is about 990 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Walt Disney World one-way?

    $67 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Allegiant Air, with prices starting from $72 and $114, respectively.

  • What are the cheapest flights from Chicago Midway Airport to Walt Disney World?

    While on average a flight from Chicago Midway Airport to Walt Disney World is generally $193, our data shows the cheapest flight currently is $43. When looking at the most popular route, (Chicago Midway - Orlando), you can expect to pay $82 for that flight.

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

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

  • How can I find direct flights from Midway 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 Midway to Walt Disney World.

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

    Yes. Cheapflights offers flight deals from Midway 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 Chicago Midway Airport to Walt Disney World?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $206). Flying from Chicago Midway Airport 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.

See more FAQs

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Alternative routes for Midway to Walt Disney World

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Midway to Walt Disney World

Discover the top 5 airlines that operate flights from Midway 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$63Average$180FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$235FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$378FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$349FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$259Average$364FlexibilityNo cancel feeOn-time69%

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