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Walt Disney World

$50+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Walt Disney World are usually found in February or July, booked 49 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 February 12, 2026.

This Expedia deal was found by Cheapflights users on 2/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Wed 3/410:28 am
MCO
-
MDW
1 stop9h 39m
Frontier
Deal found 2/8$107
This Frontier deal was found by Cheapflights users on 2/9. 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 3/17:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Thu 3/512:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Deal found 2/9$108
This Frontier deal was found by Cheapflights users on 2/9. 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 3/17:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Thu 4/306:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 2/9$109
This Trip.com deal was found by Cheapflights users on 2/8. 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.
Tue 3/37:30 am
MDW
-
MCO
1 stop6h 34m
Frontier
Fri 3/69:51 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Deal found 2/8$110
This WAYA deal was found by Cheapflights users on 2/9. 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 3/116:05 am
MDW
-
MCO
1 stop7h 20m
Frontier
Thu 3/121:50 pm
MCO
-
MDW
Nonstop3h 02m
Frontier
Deal found 2/9$111
This Priceline deal was found by Cheapflights users on 2/8. 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.
Sat 5/29:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Sat 5/22:13 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Deal found 2/8$112
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
-
MCO
1 stop6h 49m
Frontier
Mon 3/96:48 pm
MCO
-
MDW
Nonstop3h 05m
Frontier
Deal found 2/9$113
This Frontier deal was found by Cheapflights users on 2/9. 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 4/139:04 pm
MDW
-
MCO
Nonstop2h 50m
Frontier
Fri 4/176:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 2/9$114
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 4/217:30 am
MDW
-
MCO
1 stop14h 56m
Frontier
Thu 4/236:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 2/11$115
This Trip.com deal was found by Cheapflights users on 2/8. 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.
Mon 3/29:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Tue 3/310:28 am
MCO
-
MDW
1 stop9h 39m
Frontier
Deal found 2/8$116
This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:08 pm
MDW
-
MCO
Nonstop2h 48m
Frontier
Tue 3/104:05 pm
MCO
-
MDW
Nonstop3h 08m
Frontier
Deal found 2/10$117
This WAYA deal was found by Cheapflights users on 2/9. 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.
Sat 3/72:56 pm
MDW
-
MCO
Nonstop2h 46m
Frontier
Tue 3/101:30 pm
MCO
-
MDW
1 stop8h 24m
Frontier
Deal found 2/9$118

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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$107
(Expedia)

One-way from

$50
(Booking.com)

Popular in

December

Cheapest in

February

Average price

$183
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. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 12, 2026.
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 4/14

10:00 am-3:40 pm

1 stop4h 40m

Orlando

Tue 4/21

7:35 pm-9:25 pm

Nonstop2h 50m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 3/11

3:45 pm-7:20 pm

Nonstop2h 35m

Orlando

Wed 3/18

8:40 pm-10:40 pm

Nonstop3h 00m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 3/3

8:10 am-1:25 pm

1 stop4h 15m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$227

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 3/1

7:20 pm-11:00 pm

Nonstop2h 40m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$233

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 3/4

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Mon 3/9

10:50 pm-12:45 am

Nonstop2h 55m

$237

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/24

5:30 pm-9:05 pm

Nonstop2h 35m

Orlando

Sat 2/28

7:35 am-9:25 am

Nonstop2h 50m

$239

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 3/1

7:20 pm-11:00 pm

Nonstop2h 40m

Orlando

Sun 3/8

10:55 pm-12:50 am

Nonstop2h 55m

$248

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 3/8

6:07 pm-1:04 am

1 stop5h 57m

Orlando

Mon 3/16

6:00 am-12:29 pm

1 stop7h 29m

$257

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 2/25

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Sat 2/28

7:35 am-9:25 am

Nonstop2h 50m

$257

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 4/14

6:00 am-9:35 am

Nonstop2h 35m

Orlando

Sat 4/18

8:25 pm-10:15 pm

Nonstop2h 50m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 39 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 February 6, 2026.

The best time to book flights from Chicago Midway Airport to Walt Disney World is 49 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 $166). 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 February 12, 2026.

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 afternoon. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the morning.

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 February 7, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Walt Disney World flight should consider departing on Tuesday evenings when fares are most often at their lowest. Tuesday at noon 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 February 12, 2026.
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
4,280 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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
5.7
Fair
3,052 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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 4h 40m. 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 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 (72%), Southwest (69%) or Volaris (67%) 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 $211, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Chicago Midway - Orlando), you can expect to pay $67 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 $166). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$68Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$533FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$364FlexibilityNo cancel feeOn-time63%

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