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Walt Disney World

$52+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
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

Cheap 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 December 26, 2025.

This Frontier deal was found by Cheapflights users on 12/24. 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.
Wed 12/316:12 amMDW - MCO
1 stop9h 24mFrontier
Wed 12/317:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/24$158
This WAYA deal was found by Cheapflights users on 12/24. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Wed 1/75:15 pmMCO - MDW
1 stop6h 02mMultiple Airlines
Deal found 12/24$200
This Southwest deal was found by Cheapflights users on 12/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:05 amMDW - MCO
Nonstop2h 35mSouthwest
Wed 1/72:35 pmMCO - MDW
Nonstop2h 55mSouthwest
Deal found 12/24$207
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Tue 1/67:34 pmMCO - MDW
2 stops27h 43mMultiple Airlines
Deal found 12/25$208
This Frontier deal was found by Cheapflights users on 12/25. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 1/18:47 amMCO - MDW
1 stop9h 51mFrontier
Deal found 12/25$235
This Delta deal was found by Cheapflights users on 12/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:50 amMDW - MCO
1 stop5h 30mDelta
Wed 1/711:59 amMCO - MDW
1 stop6h 35mDelta
Deal found 12/24$237
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Tue 12/303:10 pmMDW - MCO
Nonstop2h 48mFrontier
Wed 12/317:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/24$246
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 12/282:16 pmMDW - MCO
Nonstop2h 45mFrontier
Thu 1/158:30 amMCO - MDW
Nonstop3h 02mFrontier
Deal found 12/24$248

Find 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 December 26, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$93
(Frontier)

One-way from

$52
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$388
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. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 26, 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

Thu 2/5

1:00 pm-4:49 pm

Nonstop2h 49m

Orlando

Sun 2/8

5:49 pm-7:52 pm

Nonstop3h 03m

$131

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/1

1:00 pm-4:49 pm

Nonstop2h 49m

Orlando

Sun 2/22

6:00 am-9:29 pm

1 stop16h 29m

$150

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 1/8

6:10 am-5:27 pm

1 stop10h 17m

Orlando

Mon 1/12

12:57 pm-10:17 pm

1 stop10h 20m

$162

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/18

5:30 pm-9:05 pm

Nonstop2h 35m

Orlando

Thu 1/29

7:05 pm-9:00 pm

Nonstop2h 55m

$168

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/18

7:35 am-11:20 am

Nonstop2h 45m

Orlando

Wed 1/21

2:35 pm-4:30 pm

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 1/26

1:55 pm-8:00 pm

1 stop5h 05m

Orlando

Sat 1/31

8:20 pm-10:10 pm

Nonstop2h 50m

$183

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/24

12:45 pm-7:40 pm

1 stop5h 55m

Orlando

Wed 1/28

2:35 pm-4:30 pm

Nonstop2h 55m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 1/21

1:25 pm-8:05 pm

1 stop5h 40m

Orlando

Wed 1/28

2:35 pm-4:30 pm

Nonstop2h 55m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/17

3:15 pm-6:50 pm

Nonstop2h 35m

Orlando

Tue 2/24

6:05 pm-10:05 pm

1 stop5h 00m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/10

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Sat 2/14

5:50 pm-7:45 pm

Nonstop2h 55m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 26 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 December 19, 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $58). 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 December 26, 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 23% 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 December 20, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Walt Disney World flight should consider departing on Thursday mornings 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 December 26, 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
4,258 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

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
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

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
3,070 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

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 35m. Fly via Frontier or Southwest to get the fastest option. The distance between Chicago Midway Airport and Walt Disney World is about 990 mi. Generally, flights for this route are nonstop.

  • What are the most reliable airlines from Chicago Midway Airport to Walt Disney World?

    No one likes to see their flight delayed. When booking a flight from Chicago Midway Airport to Walt Disney World consider choosing Frontier (86%), Southwest (74%) or Volaris (63%) as they are the most reliable in getting you off to your destination on time.

  • 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 $215, our data shows the cheapest flight currently is $60. When looking at the most popular route, (Chicago Midway - Orlando), you can expect to pay $63 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Walt Disney World (average of $58). 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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$193FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$223FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$181Average$383FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$408FlexibilityNo cancel feeOn-timeN/A

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