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Midway

$53+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheapflights Tip: The best prices from Walt Disney World to Chicago Midway are usually found in January or February, booked 13 days in advance, depart on a Friday or Thursday and return on a Friday

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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$89
(CheapOair)

One-way from

$53
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$202
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
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From Walt Disney World to Chicago Midway
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One-way flight from Walt Disney World to Chicago Midway
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Highest demand for flights based on searches. 15% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 14, 2025.

This CheapOair deal was found by Cheapflights users on 10/13. 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 11/146:10 amMCO - MDW
1 stop15h 21mFrontier
Mon 11/179:15 amMDW - MCO
1 stop11h 34mFrontier
Deal found 10/13$89
This Frontier deal was found by Cheapflights users on 10/13. 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 10/316:35 amMCO - MDW
Nonstop2h 57mFrontier
Mon 11/39:32 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 10/13$90
This Frontier deal was found by Cheapflights users on 10/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:15 amMCO - MDW
Nonstop2h 57mFrontier
Sat 11/151:37 pmMDW - MCO
1 stop9h 35mFrontier
Deal found 10/12$93
This Mytrip deal was found by Cheapflights users on 10/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:50 amMCO - MDW
Nonstop2h 57mFrontier
Mon 10/2712:03 pmMDW - MCO
1 stop11h 14mFrontier
Deal found 10/12$94
This Trip.com deal was found by Cheapflights users on 10/13. 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 11/78:24 pmMCO - MDW
Nonstop2h 56mFrontier
Mon 11/101:37 pmMDW - MCO
1 stop6h 29mFrontier
Deal found 10/13$97
This Frontier deal was found by Cheapflights users on 10/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:50 amMCO - MDW
Nonstop2h 57mFrontier
Fri 10/245:28 pmMDW - MCO
Nonstop2h 42mFrontier
Deal found 10/12$100
This Frontier deal was found by Cheapflights users on 10/14. 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 12/1211:10 amMCO - MDW
Nonstop3h 00mFrontier
Mon 12/152:15 pmMDW - MCO
Nonstop2h 45mFrontier
Deal found 10/14$102
This Frontier deal was found by Cheapflights users on 10/13. 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 11/67:15 amMCO - MDW
Nonstop2h 57mFrontier
Thu 11/1310:12 amMDW - MCO
Nonstop2h 38mFrontier
Deal found 10/13$103

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 October 14, 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

Fri 11/7

6:40 pm-8:30 pm

Nonstop2h 50m

Chicago Midway

Tue 11/11

5:05 am-8:40 am

Nonstop2h 35m

$168

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

11:10 am-1:10 pm

Nonstop3h 00m

Chicago Midway

Sun 12/7

2:45 pm-5:40 am

1 stop13h 55m

$171

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 11/5

6:50 pm-8:40 pm

Nonstop2h 50m

Chicago Midway

Sat 11/8

5:50 pm-9:25 pm

Nonstop2h 35m

$179

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 11/19

10:39 pm-10:17 pm

1 stop24h 38m

Chicago Midway

Sat 11/22

6:02 pm-9:49 pm

Nonstop2h 47m

$181

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 10/20

8:56 am-5:27 pm

1 stop9h 31m

Chicago Midway

Fri 10/24

5:52 pm-12:36 am

1 stop5h 44m

$196

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 11/15

5:44 pm-11:40 pm

1 stop6h 56m

Chicago Midway

Mon 11/17

5:34 pm-12:57 am

1 stop6h 23m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/11

11:11 am-4:18 pm

1 stop6h 07m

Chicago Midway

Wed 12/17

10:49 am-4:27 pm

1 stop4h 38m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/11

11:11 am-4:18 pm

1 stop6h 07m

Chicago Midway

Tue 12/16

9:34 am-5:00 pm

1 stop6h 26m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 11/12

4:35 pm-6:25 pm

Nonstop2h 50m

Chicago Midway

Wed 11/19

5:05 am-8:40 am

Nonstop2h 35m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/12

6:55 am-8:45 am

Nonstop2h 50m

Chicago Midway

Wed 12/17

5:05 am-8:40 am

Nonstop2h 35m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 18 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

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 October 10, 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 13 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, March is the cheapest month in which you can book a flight from Walt Disney World to Chicago Midway Airport (average of $41). 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 October 14, 2025.

It’s optimal to fly from Walt Disney World to Chicago Midway Airport in the evening. By choosing this option you can save up to 35% 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 October 12, 2025.

Travelers seeking maximum savings on their Walt Disney World to Chicago Midway Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday mornings 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 October 14, 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
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
5.8
Fair
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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 2h 50m. 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 $54. While the most popular route (Orlando - Chicago Midway) can be booked for $78 on average, our data indicates $176 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 $41). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Walt Disney World to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Walt Disney World to Midway

Discover the top 4 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$158FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$120FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$211FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$308FlexibilityNo cancel feeOn-time63%

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