HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$52+ Cheap flights from Bay Lake, FL to Midway (MDW)

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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Walt Disney World to Midway 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 Walt Disney World to Chicago Midway are usually found in January or February, booked 76 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Walt Disney World to Midway

Keep the following information in mind while searching for Walt Disney World to Midway flight deals. Data was last updated August 20, 2025.

Round-trip from

$96
(FlightHub)

One-way from

$52
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$234
From Walt Disney World to Chicago Midway
Search Deals
One-way flight from Walt Disney World to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Walt Disney World to Midway

Cheapest flights from Walt Disney World to Midway
Explore the most affordable flight options available from Walt Disney World to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/155:35 amMCO - MDW
Nonstop2h 48mFrontier
Sat 9/2010:51 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/19$96
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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.
Sun 10/129:44 amMCO - MDW
Nonstop2h 55mFrontier
Fri 10/175:28 pmMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/19$97
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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.
Fri 11/78:24 pmMCO - MDW
Nonstop2h 56mFrontier
Sun 11/910:12 amMDW - MCO
Nonstop2h 38mFrontier
Deal found 8/18$98
This CheapOair deal was found by Cheapflights users on 8/19. 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 10/37:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/19$99
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/102:26 pmMCO - MDW
Nonstop2h 54mFrontier
Mon 10/135:28 pmMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/18$100
This Booking.com deal was found by Cheapflights users on 8/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/188:25 amMCO - MDW
Nonstop2h 56mFrontier
Mon 10/205:28 pmMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/20$102
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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.
Fri 9/127:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 9/158:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/18$103
This Frontier deal was found by Cheapflights users on 8/19. 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 9/155:35 amMCO - MDW
Nonstop2h 48mFrontier
Sun 9/2110:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 8/19$105
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
Fri 9/197:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 9/228:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 8/20$106
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
Sat 8/308:00 amMCO - MDW
Nonstop2h 54mFrontier
Fri 9/59:48 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 8/20$109
This CheapOair deal was found by Cheapflights users on 8/18. 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.
Mon 9/85:35 amMCO - MDW
Nonstop2h 48mFrontier
Fri 9/129:48 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 8/18$110

Cheapflights Fare Finder

 
Customize your flight search to find flights from Walt Disney World to Midway 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 August 20, 2025.
Use the filters below to find and compare flights from Bay Lake to Chicago Midway Airport that are best for you.

Fly from

Walt Disney World

Fly to

Midway

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 9/15

5:35 am-7:23 am

Nonstop2h 48m

Chicago Midway

Sat 9/20

10:51 am-2:33 pm

Nonstop2h 42m

$96

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 10/12

9:44 am-11:39 am

Nonstop2h 55m

Chicago Midway

Fri 10/17

5:28 pm-9:10 pm

Nonstop2h 42m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 11/14

6:35 am-8:32 am

Nonstop2h 57m

Chicago Midway

Mon 11/17

9:32 am-1:14 pm

Nonstop2h 42m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 10/9

7:50 am-9:47 am

Nonstop2h 57m

Chicago Midway

Mon 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 11/7

8:24 pm-10:20 pm

Nonstop2h 56m

Chicago Midway

Sun 11/9

10:12 am-1:50 pm

Nonstop2h 38m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Mon 9/22

8:19 am-12:00 pm

Nonstop2h 41m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/27

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

Mon 9/29

5:15 pm-12:09 am

1 stop5h 54m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

Chicago Midway

Sat 10/18

11:31 am-3:11 pm

Nonstop2h 40m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 10/6

5:35 am-7:23 am

Nonstop2h 48m

Chicago Midway

Sun 10/12

12:39 pm-4:21 pm

Nonstop2h 42m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

Chicago Midway

Wed 10/15

8:05 am-2:18 pm

1 stop5h 13m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 22 results
1
2
3

Best time to book a flight from Walt Disney World to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Walt Disney World 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 Bay Lake to Chicago Midway Airport

How far ahead should I book a flight from Walt Disney World to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Walt Disney World to Midway. Price data was last updated on August 8, 2025.

The price you pay for your flight from Walt Disney World to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Walt Disney World to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Walt Disney World to Chicago Midway Airport (average of $160). Flying from Walt Disney World to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 W9D to MDW?

Find hourly flight availability from Walt Disney World to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Walt Disney World to Chicago Midway Airport as you normally would.

What is the cheapest day to fly from Walt Disney World to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Walt Disney World to Midway. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Walt Disney World to Chicago Midway Airport flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated August 20, 2025.
Get a feel of what it's like to fly with Southwest and Frontier from Bay Lake to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Walt Disney World to Midway. 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 Walt Disney World to Chicago Midway Airport?

    Departing from Walt Disney World to Chicago Midway Airport will take you 2h 48m. The distance from Walt Disney World to Chicago Midway Airport is about 990 mi. Most flights are nonstop.

  • What are the cheapest flights from Walt Disney World to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $63. While the most popular route (Orlando - Chicago Midway) can be booked for $83 on average our data indicates $202 when flying from Walt Disney World to Chicago Midway Airport.

  • Can I find deals for flights from Walt Disney World to Midway that include hotel bookings?

    Yes. In addition to deals on Walt Disney World to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Walt Disney World to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Walt Disney World to Midway.

  • Can I find deals for business class flights from Walt Disney World to Midway?

    Yes. Cheapflights offers flight deals from Walt Disney World to Midway 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 Walt Disney World to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Walt Disney World to Chicago Midway Airport (average of $160). Flying from Walt Disney World to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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 Walt Disney World to Midway

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

Top 3 airlines flying from Walt Disney World to Midway

Discover the top 3 airlines that operate flights from Walt Disney World to Midway. 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$171FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$211FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$316FlexibilityNo cancel feeOn-time63%

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.