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$58+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 64 days in advance, depart on a Friday or Thursday and return on a Saturday

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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$111
(Kiwi.com)

One-way from

$58
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$263
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. 4% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/266:22 pmMCO - MDW
Nonstop2h 55mFrontier
Mon 6/309:12 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 4/29$111
This Southwest deal was found by Cheapflights users on 4/29. 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 6/42:40 pmMCO - MDW
1 stop5h 50mSouthwest
Sat 6/75:45 pmMDW - MCO
Nonstop2h 45mSouthwest
Deal found 4/29$203
This Delta deal was found by Cheapflights users on 4/30. 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 7/196:15 amMCO - MDW
1 stop7h 14mDelta
Tue 7/229:25 amMDW - MCO
1 stop6h 21mDelta
Deal found 4/30$217
This Mytrip deal was found by Cheapflights users on 4/30. 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 6/68:24 amMCO - MDW
1 stop6h 39mMultiple Airlines
Mon 6/98:36 pmMDW - MCO
2 stops23h 01mMultiple Airlines
Deal found 4/30$244

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 May 1, 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

Thu 6/26

6:22 pm-8:17 pm

Nonstop2h 55m

Chicago Midway

Mon 6/30

9:12 pm-12:53 am

Nonstop2h 41m

$111

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 6/4

2:40 pm-7:30 pm

1 stop5h 50m

Chicago Midway

Sat 6/7

5:45 pm-9:30 pm

Nonstop2h 45m

$203

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 7/19

6:15 am-12:29 pm

1 stop7h 14m

Chicago Midway

Tue 7/22

9:25 am-4:46 pm

1 stop6h 21m

$217

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 6/6

8:24 am-2:03 pm

1 stop6h 39m

Chicago Midway

Mon 6/9

8:36 pm-8:37 pm

2 stops23h 01m

$244

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 6/2

6:22 pm-8:17 pm

Nonstop2h 55m

$58

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/24

2:45 pm-4:35 pm

Nonstop2h 50m

$90

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 6/6

8:24 am-2:03 pm

1 stop6h 39m

$101

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 6/3

3:45 pm-9:27 pm

1 stop6h 42m

$109

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 6/1

9:42 pm-7:14 pm

2 stops22h 32m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 April 25, 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 64 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 May 1, 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 March 30, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Walt Disney World to Chicago to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Comfort

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Comfort

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.
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Comfort

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Comfort

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
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Food

7.1

Comfort

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.

  • What are the cheapest airlines to fly from Walt Disney World to Chicago Midway Airport one-way?

    $58 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Allegiant Air, with prices starting from $90 and $101, respectively.

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

    Looking at all options, your cheapest flight can be booked for $53. While the most popular route (Orlando - Chicago Midway) can be booked for $116 on average our data indicates $206 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 Bay Lake?

Book flights to Bay Lake if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$165FlexibilityNo cancel feeOn-time65%
FrontierCheapest$74Average$152FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$341FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$316FlexibilityNo cancel feeOn-timeN/A

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