HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$63+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 May, 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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$126
(Cheapflightsfares)

One-way from

$63
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$209
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. 4% potential increase in price ($8 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 April 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 April 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Thu 5/810:30 amMCO - MDW
Nonstop2h 54mFrontier
Sun 5/1110:55 amMDW - MCO
Nonstop2h 43mFrontier
Deal found 4/16$126
This Delta deal was found by Cheapflights users on 4/15. 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 5/108:00 amMCO - MDW
1 stop4h 53mDelta
Sun 5/116:38 pmMDW - MCO
1 stop5h 44mDelta
Deal found 4/15$199
This Southwest deal was found by Cheapflights users on 4/17. 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 7/307:45 amMCO - MDW
Nonstop2h 45mSouthwest
Mon 8/47:30 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 4/17$217

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 April 17, 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 5/8

10:30 am-12:24 pm

Nonstop2h 54m

Chicago Midway

Sun 5/11

10:55 am-2:38 pm

Nonstop2h 43m

$126

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/10

8:00 am-11:53 am

1 stop4h 53m

Chicago Midway

Sun 5/11

6:38 pm-1:22 am

1 stop5h 44m

$199

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 5/14

8:00 am-9:50 am

Nonstop2h 50m

Chicago Midway

Wed 5/21

5:55 am-9:25 am

Nonstop2h 30m

$217

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 5/25

6:20 pm-8:17 pm

Nonstop2h 57m

$63

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/17

6:25 am-8:15 am

Nonstop2h 50m

$89

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/17

4:45 pm-9:14 pm

1 stop5h 29m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 6/2

1:40 pm-7:14 pm

1 stop6h 34m

$105

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 4/17

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 11, 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 April 17, 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 April 17, 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
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

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.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

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
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

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.

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

    $63 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 Delta, with prices starting from $89 and $99, 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 $126 on average our data indicates $203 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

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.
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to Midway flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Miami to Midway flights
Tampa to Midway flights
Fort Lauderdale to Midway flights
Sarasota to O'Hare Intl flights
Jacksonville to Midway flights
Fort Myers to Midway flights
West Palm Beach to Midway flights
Pensacola to O'Hare Intl flights
Sarasota to Midway flights
Panama City to O'Hare Intl flights
Gainesville to O'Hare Intl flights
Pensacola to Midway flights
Melbourne to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Daytona Beach to Midway flights
Valparaiso to O'Hare Intl flights
Gainesville to Midway flights
Orlando Sanford Intl to Rockford flights
St Petersburg to Rockford flights
Tallahassee to O'Hare Intl flights
Melbourne to Midway flights
Tallahassee to Midway flights
Valparaiso to Midway flights
Panama City to Midway flights
Fort Lauderdale to Rockford flights
Orlando to Rockford flights
Key West to O'Hare Intl flights
Key West to Midway flights
Valdosta to O'Hare Intl flights
Tampa to Rockford flights
Punta Gorda to Rockford flights
Pensacola to Rockford flights
Fort Myers to Rockford flights

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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$165FlexibilityNo cancel feeOn-time65%
FrontierCheapest$74Average$153FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$347FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$319FlexibilityNo cancel feeOn-timeN/A

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.