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Walt Disney World

$51+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Walt Disney World are usually found in August or July, booked 64 days in advance, depart on a Tuesday or Thursday and return on a Friday

Cheap 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 December 4, 2025.

This WAYA deal was found by Cheapflights users on 12/3. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:00 amORD - MCO
1 stop9h 20mMultiple Airlines
Wed 12/244:56 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Deal found 12/3$95
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/1612:09 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Wed 12/247:46 amMCO - ORD
Nonstop3h 32mMultiple Airlines
Deal found 12/1$96
This Mytrip deal was found by Cheapflights users on 12/2. 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.
Sat 12/131:38 pmRFD - SFB
Nonstop2h 37mAllegiant Air
Wed 12/317:10 amSFB - RFD
Nonstop2h 48mAllegiant Air
Deal found 12/2$98
This Super.com deal was found by Cheapflights users on 12/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:37 pmMDW - MCO
Nonstop2h 46mFrontier
Thu 12/187:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/2$98
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/108:00 amORD - MCO
1 stop9h 20mMultiple Airlines
Thu 12/2512:17 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Deal found 12/3$100
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/246:05 amORD - MCO
1 stop14h 20mMultiple Airlines
Thu 12/257:46 amMCO - ORD
Nonstop3h 32mMultiple Airlines
Deal found 12/1$101
This CheapOair deal was found by Cheapflights users on 12/2. 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 12/2212:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Thu 12/2512:17 pmMCO - ORD
Nonstop3h 04mSpirit Airlines
Deal found 12/2$103
This Frontier deal was found by Cheapflights users on 12/1. 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 12/123:52 pmMDW - MCO
Nonstop2h 48mFrontier
Mon 12/227:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/1$104
This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Wed 1/76:00 amMCO - ORD
1 stop11h 00mSpirit Airlines
Deal found 12/2$104
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Mon 12/158:42 pmMDW - MCO
1 stop12h 34mMultiple Airlines
Thu 12/187:58 pmMCO - MDW
Nonstop3h 00mMultiple Airlines
Deal found 12/2$105
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/3112:09 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Sat 1/105:20 amMCO - ORD
1 stop7h 15mMultiple Airlines
Deal found 12/3$106
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Sat 12/131:38 pmRFD - SFB
Nonstop2h 37mAllegiant Air
Mon 12/158:00 amSFB - RFD
Nonstop2h 48mAllegiant Air
Deal found 12/2$107

Find 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 December 4, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$94
(CheapOair)

One-way from

$51
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$290
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago (CHI) to Walt Disney World
Search Deals
One-way flight from Chicago (CHI) to Walt Disney World
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 4, 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

Tue 1/13

1:55 pm-8:00 pm

1 stop5h 05m

Orlando

Tue 1/20

10:45 am-2:30 pm

1 stop4h 45m

$98

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 1/26

5:59 pm-9:50 pm

Nonstop2h 51m

Orlando

Fri 1/30

7:35 pm-9:44 pm

Nonstop3h 09m

$115

ChicagoOrlando

RFD - SFB

RFDSFB

Chicago Greater Rockford

Fri 1/23

10:42 am-2:19 pm

Nonstop2h 37m

Orlando Sanford Intl

Mon 1/26

8:00 am-9:52 am

Nonstop2h 52m

$127

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/7

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Wed 2/11

7:25 am-9:20 am

Nonstop2h 55m

$136

ChicagoOrlando

RFD - SFB

RFDSFB

Chicago Greater Rockford

Wed 12/17

10:38 am-2:15 pm

Nonstop2h 37m

Orlando Sanford Intl

Fri 12/19

6:55 am-8:43 am

Nonstop2h 48m

$142

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 2/22

3:41 pm-7:30 pm

Nonstop2h 49m

Orlando

Mon 3/2

8:43 pm-11:00 pm

Nonstop3h 17m

$142

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 1/22

3:45 pm-7:30 pm

Nonstop2h 45m

Orlando

Mon 1/26

7:40 pm-9:50 pm

Nonstop3h 10m

$142

ChicagoOrlando

RFD - SFB

RFDSFB

Chicago Greater Rockford

Fri 1/9

10:42 am-2:19 pm

Nonstop2h 37m

Orlando Sanford Intl

Mon 1/12

8:00 am-9:52 am

Nonstop2h 52m

$146

ChicagoOrlando

RFD - SFB

RFDSFB

Chicago Greater Rockford

Tue 12/23

7:54 pm-11:31 pm

Nonstop2h 37m

Orlando Sanford Intl

Wed 12/24

7:10 am-8:58 am

Nonstop2h 48m

$150

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 1/10

4:02 pm-7:52 pm

Nonstop2h 50m

Orlando

Sat 1/17

5:45 pm-10:59 pm

1 stop6h 14m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

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 November 28, 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 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 Chicago to Walt Disney World?

Currently, March is the cheapest month in which you can book a flight from Chicago to Walt Disney World (average of $53). Flying from Chicago to Walt Disney World in June is currently the most expensive (average of $108). 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 December 4, 2025.

When flying from Chicago to Walt Disney World, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 21% versus a flight at noon.

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 November 29, 2025.

Travelers seeking maximum savings on their Chicago to Walt Disney World flight should consider departing on Tuesday evenings when fares are most often at their lowest. Monday 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 December 4, 2025.

The most flights from CHI to W9D are scheduled on a Thursday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

How much does it cost to fly round-trip from Chicago to Walt Disney World?

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 December 4, 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
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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
9,066 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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
11,047 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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
8,157 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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
3,090 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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 37m. Fly via Southwest, United Airlines, or Allegiant Air to get the fastest option. The distance from Chicago to Walt Disney World is about 1025 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Frontier ($37), Allegiant Air ($42), and Spirit Airlines ($43).

  • 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 Greater Rockford - 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 (87%), United Airlines (83%), Azul( 82%).

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

    While on average a flight from Chicago to Walt Disney World is generally $455, our data shows the cheapest flight currently is $42. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $58 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, March is the cheapest month in which you can book a flight from Chicago to Walt Disney World (average of $53). Flying from Chicago to Walt Disney World in June is currently the most expensive (average of $108). 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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Top 8 airlines flying from Chicago to Walt Disney World

Discover the top 8 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$212FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$178FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$96Average$195FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$153Average$339FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$334FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$334FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$417FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$195Average$296FlexibilityNo cancel feeOn-time62%

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