HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Walt Disney World

$79+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Walt Disney World with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago Midway to Walt Disney World are usually found in September or August, booked 57 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 June 12, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$79
(Southwest)

Popular in

October

Cheapest in

September

Average price

$307
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. 1% potential increase in price ($4 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 June 2025
Search Deals

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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:39 amMDW - MCO
Nonstop2h 41mFrontier
Mon 10/135:50 amMCO - MDW
Nonstop2h 54mFrontier
Deal found 6/12$126
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/67:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Wed 8/137:10 amMCO - MDW
Nonstop2h 45mSouthwest
Deal found 6/10$158
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/82:46 pmMDW - SFB
1 stop5h 48mAllegiant Air
Mon 8/188:10 amSFB - MDW
1 stop6h 54mAllegiant Air
Deal found 6/11$195
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/261:09 pmMDW - MCO
1 stop4h 45mDelta
Sat 8/25:30 amMCO - MDW
1 stop5h 15mDelta
Deal found 6/11$197

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 June 12, 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 10/9

8:39 am-12:20 pm

Nonstop2h 41m

Orlando

Mon 10/13

5:50 am-7:44 am

Nonstop2h 54m

$126

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 8/6

7:55 pm-11:30 pm

Nonstop2h 35m

Orlando

Wed 8/13

7:10 am-8:55 am

Nonstop2h 45m

$158

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 8/8

2:46 pm-9:34 pm

1 stop5h 48m

Orlando Sanford Intl

Mon 8/18

8:10 am-2:04 pm

1 stop6h 54m

$195

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 7/26

1:09 pm-6:54 pm

1 stop4h 45m

Orlando

Sat 8/2

5:30 am-9:45 am

1 stop5h 15m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 8/13

4:45 pm-8:25 pm

Nonstop2h 40m

$79

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/20

4:29 pm-5:39 am

1 stop12h 10m

$85

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 8/25

3:52 pm-4:57 pm

1 stop24h 05m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 8/9

10:30 am-6:41 pm

1 stop7h 11m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 8/4

1:11 pm-8:43 pm

1 stop6h 32m

$103

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/5

5:33 pm-10:27 pm

2 stops27h 54m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 9, 2025.

The best time to book flights from Chicago Midway Airport to Walt Disney World is 57 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 June 12, 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 June 8, 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 June 12, 2025.

The most flights from MDW to W9D are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 June 12, 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
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
725 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

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?

    $79 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 $85 and $98, 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 $258, our data shows the cheapest flight currently is $47. When looking at the most popular route, (Chicago Midway - Orlando), you can expect to pay $126 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

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.

Alternative routes for Midway to Walt Disney World

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
Midway to Miami flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Jacksonville flights
Midway to Tampa flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
O'Hare Intl to Pensacola flights
O'Hare Intl to Panama City flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Myers flights
Midway to Sarasota flights
Midway to West Palm Beach flights
Midway to Jacksonville flights
Midway to Key West flights
Midway to Panama City flights
O'Hare Intl to Daytona Beach flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Valparaiso flights
O'Hare Intl to St Petersburg flights
Midway to Pensacola flights
Midway to Orlando Sanford Intl flights
Rockford to St Petersburg flights
Midway to Daytona Beach flights
O'Hare Intl to Gainesville flights
Midway to Melbourne flights
O'Hare Intl to Melbourne flights
O'Hare Intl to Orlando Sanford Intl flights
Midway to Gainesville flights
O'Hare Intl to Punta Gorda flights
O'Hare Intl to Tallahassee flights
Midway to Valparaiso flights
Midway to Punta Gorda flights
Rockford to Punta Gorda flights
Midway to Tallahassee flights
Midway to Valdosta flights
O'Hare Intl to Valdosta flights
O'Hare Intl to Destin flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$214FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$179FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$181Average$385FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$318FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$389FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.