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Walt Disney World

$50+ Cheap flights from Chicago (CHI) to Bay Lake, FL

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Walt Disney World are usually found in August or September, booked 29 days in advance, depart on a Tuesday or Thursday and return on a Friday

Cheap flight deals from Chicago to Walt Disney World

Keep the following information in mind while searching for Chicago to Walt Disney World flight deals. Data was last updated August 20, 2025.

Round-trip from

$96
(Kiwi.com)

One-way from

$50
(Booking.com)

Popular in

March

Cheapest in

August

Average price

$188
From Chicago (CHI) to Walt Disney World
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One-way flight from Chicago (CHI) to Walt Disney World
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Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Walt Disney World

Cheapest flights from Chicago to Walt Disney World
Explore the most affordable flight options available from Chicago to Walt Disney World. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Tue 9/166:30 amORD - MCO
Nonstop2h 43mMultiple Airlines
Thu 9/255:24 pmMCO - ORD
Nonstop3h 20mMultiple Airlines
Deal found 8/18$96
This Frontier deal was found by Cheapflights users on 8/19. 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 9/59:48 amMDW - MCO
Nonstop2h 40mFrontier
Mon 9/85:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 8/19$96
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Tue 9/165:17 pmORD - MCO
Nonstop2h 49mMultiple Airlines
Mon 9/225:24 pmMCO - ORD
Nonstop3h 20mMultiple Airlines
Deal found 8/20$97
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 9/199:48 amMDW - MCO
Nonstop2h 40mFrontier
Sat 9/278:00 amMCO - MDW
Nonstop2h 51mFrontier
Deal found 8/19$97
This Priceline deal was found by Cheapflights users on 8/19. 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.
Fri 9/58:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
Tue 9/97:50 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Deal found 8/19$98
This Frontier deal was found by Cheapflights users on 8/18. 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 10/1811:31 amMDW - MCO
Nonstop2h 40mFrontier
Sat 10/258:25 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 8/18$98
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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.
Mon 9/88:49 pmORD - MCO
Nonstop2h 46mFrontier
Thu 9/115:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 8/19$99
This Frontier deal was found by Cheapflights users on 8/19. 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 10/1811:31 amMDW - MCO
Nonstop2h 40mFrontier
Thu 10/237:50 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 8/19$99
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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.
Tue 9/166:30 amORD - MCO
Nonstop2h 43mSpirit Airlines
Fri 9/197:50 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Deal found 8/18$100
This Priceline deal was found by Cheapflights users on 8/18. 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.
Sat 11/111:36 amMDW - MCO
Nonstop2h 40mFrontier
Mon 11/36:35 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 8/18$100
This CheapOair deal was found by Cheapflights users on 8/19. 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.
Mon 9/158:49 pmORD - MCO
Nonstop2h 46mFrontier
Mon 9/225:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 8/19$101
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Wed 10/228:00 amORD - MCO
Nonstop2h 48mFrontier
Thu 10/236:05 amMCO - ORD
Nonstop3h 09mFrontier
Deal found 8/18$102

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Walt Disney World 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 August 20, 2025.
Use the filters below to find and compare flights from Chicago to Bay Lake that are best for you.

Fly from

Chicago

Fly to

Walt Disney World

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/5

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Mon 9/8

5:35 am-7:23 am

Nonstop2h 48m

$96

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 9/27

10:51 am-2:33 pm

Nonstop2h 42m

Orlando

Mon 9/29

6:00 am-4:00 pm

1 stop11h 00m

$97

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/15

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Mon 9/22

5:35 am-7:23 am

Nonstop2h 48m

$97

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/22

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Mon 9/29

5:35 am-7:23 am

Nonstop2h 48m

$97

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 9/27

8:00 am-11:57 am

Nonstop2h 57m

Orlando

Mon 9/29

6:00 am-10:31 am

1 stop5h 31m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

Orlando

Sat 10/18

8:25 am-10:21 am

Nonstop2h 56m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/29

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Fri 10/3

7:00 am-8:53 am

Nonstop2h 53m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/12

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Sat 9/13

8:00 am-9:51 am

Nonstop2h 51m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 11/3

9:32 am-1:14 pm

Nonstop2h 42m

Orlando

Sat 11/8

8:30 am-10:26 am

Nonstop2h 56m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 10/18

11:31 am-3:11 pm

Nonstop2h 40m

Orlando

Fri 10/24

2:26 pm-4:20 pm

Nonstop2h 54m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Walt Disney World

Have a flexible travel schedule? Discover the best time to fly to Walt Disney World from Chicago 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 Chicago to Bay Lake

How far ahead should I book a flight from Chicago to Walt Disney World?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Walt Disney World. Price data was last updated on August 8, 2025.

The price you pay for your flight from Chicago to Walt Disney World may vary depending on when you book. For the best chance of a lower fare, look to book 29 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 Chicago to Walt Disney World?

Currently, May is the cheapest month in which you can book a flight from Chicago to Walt Disney World (average of $206). Flying from Chicago to Walt Disney World in November is currently the most expensive (average of $289). 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 CHI to W9D?

Find hourly flight availability from Chicago to Walt Disney World. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Walt Disney World as you normally would.

What is the cheapest day to fly from Chicago to Walt Disney World?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Walt Disney World. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Chicago to Walt Disney World flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Walt Disney World

Explore weekly flight availability from Chicago to Walt Disney World. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 20, 2025.

The most flights from CHI to W9D are scheduled on a Thursday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

Reviews of airlines servicing Walt Disney World

Get insights into the airlines that provide service to Walt Disney World. 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 Walt Disney World. Reviews last updated August 20, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to Bay Lake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,039 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Walt Disney World. 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 Chicago to Walt Disney World?

    There are many flights that can get you from Chicago to Walt Disney World in 2h 32m. Fly via Frontier, Spirit Airlines, or Allegiant Air to get the fastest option. The distance from Chicago to Walt Disney World is about 1025 mi. Generally, flights for this route are nonstop.

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

    The cheapest airlines for a one-way flight from Chicago to Walt Disney World are Allegiant Air ($50), Spirit Airlines ($51), and Frontier ($52).

  • What are the most popular routes from Chicago to Walt Disney World?

    The most popular flight routes from Chicago to Walt Disney World are Chicago O'Hare Intl - Orlando, Chicago Midway - Orlando and Chicago Midway - Orlando Sanford Intl.

  • What are the most reliable airlines from Chicago to Walt Disney World?

    Before booking your flight to Walt Disney World from Chicago, check out the most reliable airlines to get you to your destination on time: Copa Airlines (90%), Spirit Airlines (88%), Southwest( 84%).

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

    While on average a flight from Chicago to Walt Disney World is generally $478, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $79 for that flight.

  • Can I find deals for flights from Chicago to Walt Disney World that include hotel bookings?

    Yes. In addition to deals on Chicago to Walt Disney World flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Walt Disney World?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Walt Disney World.

  • Can I find deals for business class flights from Chicago to Walt Disney World?

    Yes. Cheapflights offers flight deals from Chicago to Walt Disney World 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 Chicago to Walt Disney World?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Walt Disney World (average of $206). Flying from Chicago to Walt Disney World in November is currently the most expensive (average of $289). 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.

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Alternative routes for Chicago to Walt Disney World

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Top 7 airlines flying from Chicago to Walt Disney World

Discover the top 7 airlines that operate flights from Chicago to Walt Disney World. 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$216FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$119Average$199FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$368FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$159Average$337FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$369FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$375FlexibilityNo cancel feeOn-timeN/A

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