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Midway

$50+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Find cheap flights from Walt Disney World to Midway with Cheapflights

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Cheapflights Tip: The best prices from Walt Disney World to Chicago Midway are usually found in January or October, booked 13 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 November 6, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$78
(Priceline)

One-way from

$50
(Priceline)

Popular in

June

Cheapest in

January

Average price

$234
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. 18% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This Priceline deal was found by Cheapflights users on 11/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:04 pmMCO - MDW
Nonstop3h 00mFrontier
Sun 1/1110:18 amMDW - MCO
Nonstop2h 46mFrontier
Deal found 11/4$78
This CheapOair deal was found by Cheapflights users on 11/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:33 pmMCO - MDW
Nonstop2h 56mFrontier
Thu 11/275:30 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$79
This CheapOair deal was found by Cheapflights users on 11/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:33 pmMCO - MDW
Nonstop2h 56mFrontier
Mon 11/245:47 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$81
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/128:40 pmMCO - MDW
Nonstop2h 59mFrontier
Mon 12/153:52 pmMDW - MCO
1 stop6h 49mFrontier
Deal found 11/6$83
This Frontier deal was found by Cheapflights users on 11/4. 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.
Thu 12/412:57 pmMCO - MDW
1 stop10h 15mFrontier
Mon 12/83:10 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$84
This Flightnetwork deal was found by Cheapflights users on 11/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:40 pmMCO - MDW
Nonstop2h 59mFrontier
Mon 12/812:18 pmMDW - MCO
1 stop16h 13mFrontier
Deal found 11/4$85
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/202:34 pmMCO - MDW
Nonstop2h 56mFrontier
Sun 11/235:30 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/5$86
This eDestinos deal was found by Cheapflights users on 11/4. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:10 pmMCO - MDW
Nonstop2h 57mFrontier
Mon 11/245:47 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$91
This Frontier deal was found by Cheapflights users on 11/6. 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.
Sat 11/223:10 pmMCO - MDW
Nonstop2h 57mFrontier
Fri 11/284:46 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/6$92
This CheapOair deal was found by Cheapflights users on 11/5. 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.
Sun 11/232:34 pmMCO - MDW
Nonstop2h 56mFrontier
Mon 11/245:47 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/5$94
This Trip.com deal was found by Cheapflights users on 11/4. 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 11/148:14 pmMCO - MDW
Nonstop2h 56mFrontier
Mon 11/179:27 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 11/4$96

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 November 6, 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 1/30

7:05 pm-9:00 pm

Nonstop2h 55m

Chicago Midway

Tue 2/3

7:35 am-11:20 am

Nonstop2h 45m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 1/7

2:35 pm-4:30 pm

Nonstop2h 55m

Chicago Midway

Sun 1/11

6:00 pm-9:40 pm

Nonstop2h 40m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 1/10

8:20 pm-10:10 pm

Nonstop2h 50m

Chicago Midway

Sun 1/11

6:05 pm-11:15 pm

1 stop4h 10m

$147

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/3

7:30 am-9:20 am

Nonstop2h 50m

Chicago Midway

Wed 12/10

10:40 am-2:15 pm

Nonstop2h 35m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 12/9

7:30 am-9:20 am

Nonstop2h 50m

Chicago Midway

Wed 12/10

5:05 am-8:40 am

Nonstop2h 35m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

6:50 pm-8:40 pm

Nonstop2h 50m

Chicago Midway

Sun 12/7

6:50 am-10:25 am

Nonstop2h 35m

$159

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

6:50 pm-8:40 pm

Nonstop2h 50m

Chicago Midway

Mon 12/8

5:05 am-8:40 am

Nonstop2h 35m

$159

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 11/24

9:00 am-1:40 pm

1 stop5h 40m

Chicago Midway

Tue 12/2

4:35 pm-8:10 pm

Nonstop2h 35m

$168

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 12/6

6:05 pm-7:55 pm

Nonstop2h 50m

Chicago Midway

Wed 12/10

1:25 pm-6:50 pm

1 stop4h 25m

$183

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 2/11

7:05 pm-9:00 pm

Nonstop2h 55m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

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

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 31, 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 November 6, 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 39% 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 November 2, 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 November 6, 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
4,240 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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
3,116 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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 55m. 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 $42. While the most popular route (Orlando - Chicago Midway) can be booked for $84 on average, our data indicates $147 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$158FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$120FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$206FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$310FlexibilityNo cancel feeOn-time63%

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