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$59+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
1 adult, Economy
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The best prices from Walt Disney World to Chicago Midway are usually found in February or April, booked 66 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Walt Disney World to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Walt Disney World (W9D) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 17, 2025.

Round-trip from

$104
(Frontier)

One-way from

$59
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$170
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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High demand for flights, 7% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 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 January 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/16. 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.
Fri 1/2412:38 pmMCO - MDW
Nonstop3h 04mFrontier
Sun 1/2610:58 amMDW - MCO
Nonstop2h 47mFrontier
Deal found 1/16$98
This Delta deal was found by Cheapflights users on 1/15. 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 2/159:00 amMCO - MDW
1 stop6h 53mDelta
Mon 2/242:08 pmMDW - MCO
1 stop6h 05mDelta
Deal found 1/15$197
This Southwest deal was found by Cheapflights users on 1/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/47:10 amMCO - MDW
Nonstop2h 55mSouthwest
Sat 2/83:55 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 1/15$237

Find flights from Walt Disney World to Midway within your budget

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/30

9:14 pm-12:17 am

1 stop28h 03m

Chicago Midway

Sun 2/2

10:58 am-2:45 pm

Nonstop2h 47m

$101

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 3/12

7:15 am-9:15 am

Nonstop3h 00m

Chicago Midway

Tue 3/18

5:35 am-9:10 am

Nonstop2h 35m

$191

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 2/15

9:00 am-2:53 pm

1 stop6h 53m

Chicago Midway

Wed 2/19

12:44 pm-7:42 pm

1 stop5h 58m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 2/3

5:35 am-9:05 pm

1 stop16h 30m

$59

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/18

9:05 pm-11:00 pm

Nonstop2h 55m

$96

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/20

5:30 am-10:12 am

1 stop5h 42m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 5/26

1:40 pm-7:14 pm

1 stop6h 34m

$148

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 3/12

6:44 pm-5:36 pm

3 stops23h 52m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

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.

Travel insights for flights from Walt Disney World to Midway

Get recent, data-driven insights about flights from Walt Disney World to Midway including ideal travel times, pricing trends, and more.

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 January 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 66 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 January 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 December 16, 2024.

Travelers seeking maximum savings on their Walt Disney World to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Saturday 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 January 17, 2025.
Peruse reviews from past customers who have flown with Frontier, Delta and Southwest 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
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,435 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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?

    $59 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 $96 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 $64. While the most popular route (Orlando - Chicago Midway) can be booked for $88 on average our data indicates $229 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$155FlexibilityNo cancel feeOn-time65%
FrontierCheapest$74Average$149FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$340FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$347FlexibilityNo cancel feeOn-timeN/A
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