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Midway

$49+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap 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 February 4, 2026.

This Super.com deal was found by Cheapflights users on 2/3. 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.
Thu 4/306:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Sun 5/39:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 2/3$87
This Frontier deal was found by Cheapflights users on 2/3. 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.
Fri 4/246:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Mon 4/279:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 2/3$88
This Frontier deal was found by Cheapflights users on 2/2. 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.
Tue 3/104:05 pm
MCO
-
MDW
Nonstop3h 08m
Frontier
Mon 3/169:51 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 2/2$91
This Super.com deal was found by Cheapflights users on 2/2. 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 2/2012:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sat 2/218:00 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 2/2$92
This Super.com deal was found by Cheapflights users on 2/3. 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.
Thu 3/512:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Thu 3/129:10 am
MDW
-
MCO
Nonstop2h 45m
Frontier
Deal found 2/3$97
This Frontier deal was found by Cheapflights users on 2/3. 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.
Thu 3/121:50 pm
MCO
-
MDW
Nonstop3h 02m
Frontier
Mon 3/169:51 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 2/3$98
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Fri 3/139:51 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Tue 3/1711:19 am
MDW
-
MCO
Nonstop2h 45m
Frontier
Deal found 2/3$100
This Trip.com deal was found by Cheapflights users on 2/4. 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.
Fri 3/69:51 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Mon 3/96:15 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 2/4$101
This Frontier deal was found by Cheapflights users on 2/4. 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 3/166:48 pm
MCO
-
MDW
Nonstop3h 05m
Frontier
Tue 3/244:33 pm
MDW
-
MCO
Nonstop2h 46m
Frontier
Deal found 2/4$106
This Super.com deal was found by Cheapflights users on 2/1. 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.
Sat 2/1412:49 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sat 2/218:00 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 2/1$107
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 5/146:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Tue 5/197:30 am
MDW
-
MCO
1 stop8h 14m
Frontier
Deal found 2/3$110

Find 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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$87
(Super.com)

One-way from

$49
(Super.com)

Popular in

June

Cheapest in

January

Average price

$239
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
Search Deals
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. 17% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 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 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 February 4, 2026.
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

Fri 3/6

6:48 pm-8:53 pm

Nonstop3h 05m

Chicago Midway

Sat 3/7

6:15 am-10:05 am

Nonstop2h 50m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/13

9:51 pm-11:51 pm

Nonstop3h 00m

Chicago Midway

Tue 3/17

11:19 am-3:04 pm

Nonstop2h 45m

$100

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/13

11:05 am-1:08 pm

Nonstop3h 03m

Chicago Midway

Mon 3/16

9:51 pm-1:38 am

Nonstop2h 47m

$100

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/6

11:05 am-1:08 pm

Nonstop3h 03m

Chicago Midway

Sat 3/7

9:16 pm-5:00 pm

1 stop18h 44m

$141

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 3/5

12:44 pm-10:29 pm

1 stop10h 45m

Chicago Midway

Thu 3/12

2:41 pm-11:50 pm

2 stops8h 09m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 2/23

5:01 am-1:08 pm

1 stop9h 07m

Chicago Midway

Sat 2/28

8:00 am-11:49 am

Nonstop2h 49m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/24

6:16 am-1:02 pm

1 stop7h 46m

Chicago Midway

Thu 3/26

4:55 pm-10:55 am

1 stop17h 00m

$171

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/3

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Tue 3/10

6:15 pm-9:55 pm

Nonstop2h 40m

$177

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 3/19

3:40 pm-5:44 pm

Nonstop3h 04m

Chicago Midway

Sun 3/22

6:20 am-7:32 am

1 stop24h 12m

$183

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 4/23

2:47 pm-7:31 pm

1 stop5h 44m

Chicago Midway

Sun 4/26

2:20 pm-8:21 pm

1 stop5h 01m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 20 results
1
2

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

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

Currently, March is the cheapest month in which you can book a flight from Walt Disney World to Chicago Midway Airport (average of $43). Flying from Walt Disney World to Chicago Midway Airport in July is currently the most expensive (average of $126). 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 February 4, 2026.

It’s optimal to fly from Walt Disney World to Chicago Midway Airport at noon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the morning.

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 January 31, 2026.

Travelers seeking maximum savings on their Walt Disney World to Chicago Midway Airport flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday afternoons 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 February 4, 2026.
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
4,274 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
5.7
Fair
3,052 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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 3h 05m. The distance from Walt Disney World to Chicago Midway Airport is about 990 mi. Most flights are nonstop.

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

    Before booking your flight to Chicago Midway Airport from Walt Disney World, check out the most reliable airlines to get you to your destination on time: Southwest (66%), Volaris (60%), Frontier( 51%).

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

    Looking at all options, your cheapest flight can be booked for $51. While the most popular route (Orlando - Chicago Midway) can be booked for $88 on average, our data indicates $223 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, March is the cheapest month in which you can book a flight from Walt Disney World to Chicago Midway Airport (average of $43). Flying from Walt Disney World to Chicago Midway Airport in July is currently the most expensive (average of $126). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$155FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$196FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$295FlexibilityNo cancel feeOn-time63%

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