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Walt Disney World

$55+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Walt Disney World are usually found in September or August, booked 31 days in advance, depart on a Saturday or Thursday 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$114
(Cheapflightsfares)

One-way from

$55
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$180
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
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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. 17% potential increase in price ($51 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/229:12 pmMDW - MCO
Nonstop2h 45mFrontier
Sun 5/256:20 pmMCO - MDW
Nonstop2h 57mFrontier
Deal found 4/30$114
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 6/77:05 pmMDW - MCO
Nonstop2h 40mSouthwest
Tue 6/106:20 amMCO - MDW
Nonstop2h 50mSouthwest
Deal found 4/29$197
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/245:55 pmMDW - MCO
1 stop4h 59mDelta
Sun 5/256:15 amMCO - MDW
1 stop6h 38mDelta
Deal found 4/29$200
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 5/308:04 pmMDW - SFB
1 stop18h 58mAllegiant Air
Thu 6/59:53 pmSFB - MDW
1 stop22h 53mAllegiant Air
Deal found 4/29$210
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Fri 6/68:36 pmMDW - MCO
1 stop11h 25mAllegiant Air
Mon 6/98:24 amMCO - MDW
1 stop6h 39mAllegiant Air
Deal found 4/30$225

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 May 1, 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 5/22

9:12 pm-12:57 am

Nonstop2h 45m

Orlando

Sun 5/25

6:20 pm-8:17 pm

Nonstop2h 57m

$114

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 6/7

7:05 pm-10:45 pm

Nonstop2h 40m

Orlando

Tue 6/10

6:20 am-8:10 am

Nonstop2h 50m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 5/24

5:55 pm-11:54 pm

1 stop4h 59m

Orlando

Sun 5/25

6:15 am-11:53 am

1 stop6h 38m

$200

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 5/30

8:04 pm-4:02 pm

1 stop18h 58m

Orlando Sanford Intl

Thu 6/5

9:53 pm-7:46 pm

1 stop22h 53m

$210

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 6/6

8:36 pm-9:01 am

1 stop11h 25m

Orlando

Mon 6/9

8:24 am-2:03 pm

1 stop6h 39m

$225

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 5/8

1:19 pm-5:03 pm

Nonstop2h 44m

$55

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 7/4

5:30 pm-9:15 pm

Nonstop2h 45m

$90

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 5/30

8:04 pm-8:42 pm

1 stop23h 38m

$100

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 5/25

4:15 pm-12:24 am

1 stop7h 09m

$100

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 6/6

8:36 pm-9:01 am

1 stop11h 25m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 11 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 April 25, 2025.

The best time to book flights from Chicago Midway Airport to Walt Disney World is 31 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 May 1, 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 March 30, 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. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Walt Disney World by month

Plan your trip to Walt Disney World by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Walt Disney World ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Walt Disney World when rainfall is around 2.4 in.

Temperature in Walt Disney World by month

Plan your trip to Walt Disney World by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Walt Disney World, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 May 1, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Chicago to Walt Disney World have to say. 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
4,294 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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.
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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.

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

    $55 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 $90 and $100, 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 $209, our data shows the cheapest flight currently is $62. When looking at the most popular route, (Chicago Midway - Orlando), you can expect to pay $114 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$69Average$215FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$179FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$128Average$334FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$180Average$402FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$333FlexibilityNo cancel feeOn-timeN/A

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