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Walt Disney World

$44+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
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 September, booked 52 days in advance, depart on a Thursday or Friday and return on a Friday

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 November 5, 2025.

This Priceline deal was found by Cheapflights users on 11/3. 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 11/179:27 amMDW - MCO
Nonstop2h 42mFrontier
Fri 11/219:33 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 11/3$100
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Fri 11/219:30 amMDW - MCO
1 stop10h 54mFrontier
Fri 12/128:40 pmMCO - MDW
Nonstop2h 59mFrontier
Deal found 11/4$101
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Mon 11/108:00 amMDW - MCO
Nonstop2h 41mFrontier
Sat 11/158:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 11/3$102
This Frontier deal was found by Cheapflights users on 11/4. 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.
Sun 11/1610:12 amMDW - MCO
Nonstop2h 38mFrontier
Sat 11/223:10 pmMCO - MDW
Nonstop2h 57mFrontier
Deal found 11/4$103
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.
Mon 12/1512:35 pmMDW - MCO
1 stop11h 24mFrontier
Mon 12/227:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 11/5$104
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.
Mon 12/153:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 12/187:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 11/5$106
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/1511:36 amMDW - MCO
Nonstop2h 40mFrontier
Sat 11/223:10 pmMCO - MDW
Nonstop2h 57mFrontier
Deal found 11/4$107
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Sat 11/1511:36 amMDW - MCO
Nonstop2h 40mFrontier
Thu 11/202:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 11/4$108
This Frontier deal was found by Cheapflights users on 11/4. 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 11/1511:36 amMDW - MCO
Nonstop2h 40mFrontier
Sun 11/232:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 11/4$109
This Frontier deal was found by Cheapflights users on 11/4. 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 12/66:00 amMDW - MCO
1 stop5h 39mFrontier
Sat 12/134:10 pmMCO - MDW
1 stop6h 12mFrontier
Deal found 11/4$110
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:42 pmMDW - MCO
1 stop11h 40mFrontier
Mon 12/157:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 11/5$111
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/145:35 pmMDW - SFB
1 stop21h 35mAllegiant Air
Sun 11/169:55 pmSFB - MDW
1 stop15h 07mAllegiant Air
Deal found 11/4$230

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 November 5, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$100
(Priceline)

One-way from

$44
(CheapOair)

Popular in

December

Cheapest in

August

Average price

$258
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago Midway to Walt Disney World
Search Deals
One-way flight from Chicago Midway to Walt Disney World
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 5, 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

Tue 1/27

7:35 am-11:20 am

Nonstop2h 45m

Orlando

Sun 2/1

6:50 am-8:45 am

Nonstop2h 55m

$137

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/3

3:15 pm-6:50 pm

Nonstop2h 35m

Orlando

Fri 2/6

8:35 pm-10:25 pm

Nonstop2h 50m

$137

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/3

7:35 am-11:20 am

Nonstop2h 45m

Orlando

Tue 2/10

10:45 am-2:30 pm

1 stop4h 45m

$143

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 12/16

9:30 am-1:10 pm

Nonstop2h 40m

Orlando

Wed 12/31

5:40 pm-7:30 pm

Nonstop2h 50m

$147

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/6

12:15 pm-7:30 pm

1 stop6h 15m

Orlando

Sat 1/10

8:20 pm-10:10 pm

Nonstop2h 50m

$147

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 12/9

10:49 am-5:27 pm

1 stop5h 38m

Orlando

Sat 12/13

6:00 am-12:34 pm

1 stop7h 34m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/10

11:21 am-7:36 pm

1 stop7h 15m

Orlando

Tue 1/13

6:35 pm-10:09 pm

1 stop4h 34m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 12/13

1:00 pm-4:35 pm

Nonstop2h 35m

Orlando

Tue 12/16

2:45 pm-4:35 pm

Nonstop2h 50m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 2/2

5:30 pm-9:05 pm

Nonstop2h 35m

Orlando

Thu 2/5

4:00 pm-6:00 pm

Nonstop3h 00m

$203

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 11/17

4:12 pm-11:05 pm

1 stop5h 53m

Orlando Sanford Intl

Thu 11/20

7:16 pm-1:21 pm

1 stop19h 05m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 35 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 October 31, 2025.

The best time to book flights from Chicago Midway Airport to Walt Disney World is 52 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $63). Flying from Chicago Midway Airport to Walt Disney World in June is currently the most expensive (average of $167). 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 November 5, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Walt Disney World in the evening. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight at noon.

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 November 2, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Walt Disney World flight should consider departing on Wednesday afternoons 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.

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 5, 2025.
Read reviews from past customers who have flown Southwest, Spirit Airlines, 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
4,239 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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.
Spirit Airlines
6.3
Okay
8,113 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
3,115 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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 45m. Fly via 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?

    $50 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Allegiant Air, with prices starting from $69 and $110, 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 $194, our data shows the cheapest flight currently is $53. When looking at the most popular route, (Chicago Midway - Orlando), you can expect to pay $58 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $63). Flying from Chicago Midway Airport to Walt Disney World in June is currently the most expensive (average of $167). 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 4 airlines flying from Midway to Walt Disney World

Discover the top 4 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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$228FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$379FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$402FlexibilityNo cancel feeOn-timeN/A

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