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

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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in September or October, booked 87 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Walt Disney World to Chicago

Keep the following information in mind while searching for Walt Disney World to Chicago flight deals. Data was last updated September 11, 2025.

Round-trip from

$87
(Kiwi.com)

One-way from

$50
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$125
From Walt Disney World to Chicago (CHI)
Search Deals
One-way flight from Walt Disney World to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Walt Disney World to Chicago

Cheapest flights from Walt Disney World to Chicago
Explore the most affordable flight options available from Walt Disney World to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 10/35:24 pmMCO - ORD
Nonstop3h 20mFrontier
Sun 10/58:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/10$87
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 9/185:24 pmMCO - ORD
Nonstop3h 20mFrontier
Mon 9/228:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/9$88
This Priceline deal was found by Cheapflights users on 9/9. 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.
Thu 9/184:43 pmMCO - ORD
Nonstop3h 07mMultiple Airlines
Mon 9/228:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
Deal found 9/9$89
This FlightHub deal was found by Cheapflights users on 9/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/314:08 pmSFB - RFD
Nonstop2h 45mAllegiant Air
Mon 11/35:48 pmRFD - SFB
Nonstop2h 30mAllegiant Air
Deal found 9/10$90
This Mytrip deal was found by Cheapflights users on 9/11. 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.
Thu 10/96:05 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Tue 10/146:58 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Deal found 9/11$90
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/257:50 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Fri 10/38:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
Deal found 9/10$91
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/96:05 amMCO - ORD
Nonstop3h 09mFrontier
Mon 10/136:35 pmORD - MCO
Nonstop2h 59mFrontier
Deal found 9/10$92
This Frontier deal was found by Cheapflights users on 9/10. 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 9/271:02 pmMCO - ORD
Nonstop3h 15mFrontier
Mon 9/298:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/10$94
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/25:24 pmMCO - ORD
Nonstop3h 20mFrontier
Mon 10/68:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/10$95
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/295:24 pmMCO - ORD
Nonstop3h 20mFrontier
Fri 10/38:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/10$96
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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.
Sat 9/131:02 pmMCO - ORD
Nonstop3h 15mFrontier
Fri 9/198:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/8$97
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/37:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 9/11$103

Cheapflights Fare Finder

 
Customize your flight search to find flights from Walt Disney World to Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Bay Lake to Chicago that are best for you.

Fly from

Walt Disney World

Fly to

Chicago

Route

Depart

Return

Price

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 10/31

4:08 pm-5:53 pm

Nonstop2h 45m

Chicago Greater Rockford

Mon 11/3

5:48 pm-9:18 pm

Nonstop2h 30m

$90

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/31

6:35 am-8:32 am

Nonstop2h 57m

Chicago Midway

Mon 11/3

9:32 am-1:14 pm

Nonstop2h 42m

$103

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Sat 12/6

11:00 am-12:48 pm

Nonstop2h 48m

Chicago Greater Rockford

Mon 12/8

10:38 am-2:15 pm

Nonstop2h 37m

$104

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/10

2:26 pm-4:20 pm

Nonstop2h 54m

Chicago Midway

Mon 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

$105

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 10/8

6:15 am-8:00 am

Nonstop2h 45m

Chicago Greater Rockford

Mon 10/13

7:47 pm-11:17 pm

Nonstop2h 30m

$107

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/10

2:26 pm-4:20 pm

Nonstop2h 54m

Chicago Midway

Tue 10/14

8:05 am-6:52 pm

1 stop9h 47m

$123

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 10/3

12:33 pm-2:18 pm

Nonstop2h 45m

Chicago Greater Rockford

Mon 10/6

7:40 pm-11:10 pm

Nonstop2h 30m

$129

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/10

9:40 pm-11:25 pm

Nonstop2h 45m

Chicago Midway

Tue 10/14

8:05 pm-11:35 pm

Nonstop2h 30m

$140

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 11/18

9:05 am-11:10 am

Nonstop3h 05m

Chicago O'Hare Intl

Wed 11/19

1:45 pm-8:10 pm

1 stop5h 25m

$143

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 10/28

9:00 am-12:05 pm

1 stop4h 05m

Chicago Midway

Tue 10/28

5:30 pm-9:00 pm

Nonstop2h 30m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Use this chart to determine the optimal time to book a round-trip flight from Walt Disney World to Chicago. Price data was last updated on August 29, 2025.

The price you pay for your flight from Walt Disney World to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 86 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?

Currently, August is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $245). Flying from Walt Disney World to Chicago in March is currently the most expensive (average of $321). 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 CHI?

Find hourly flight availability from Walt Disney World to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 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 as you normally would.

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

Use this chart to determine the cheapest time to fly round-trip from Walt Disney World to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Walt Disney World to Chicago flight should consider departing on Thursday 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 Walt Disney World to Chicago

Explore weekly flight availability from Walt Disney World to Chicago. 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 September 11, 2025.

The most flights from W9D to CHI are scheduled on a Thursday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Bay Lake to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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 Chicago. 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 Walt Disney World to Chicago?

    Departing from Walt Disney World to Chicago will take you 2h 45m. The distance from Walt Disney World to Chicago is about 1025 mi. Generally, flights for this route are nonstop.

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

    One-way options have recently been found by users for as low as $52 on Allegiant Air. Other airlines that offer cheap prices include Frontier from $54 and United Airlines from $67 one-way.

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

    When deciding which route to take from Walt Disney World to Chicago consider Orlando - Chicago O'Hare Intl, Orlando - Chicago Midway or Orlando Sanford Intl - Chicago Greater Rockford as they are the most popular.

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

    Before booking your flight to Chicago from Walt Disney World, check out the most reliable airlines to get you to your destination on time: Brussels Airlines (80%), Cathay Pacific (79%), United Airlines( 78%).

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

    Looking at all options, your cheapest flight can be booked for $52. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $65 on average, our data indicates $1,006 when flying from Walt Disney World to Chicago.

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

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

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

    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 Chicago.

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

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

    Currently, August is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $245). Flying from Walt Disney World to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

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

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Alternative routes for Walt Disney World to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Walt Disney World to Chicago

Discover the top 7 airlines that operate flights from Walt Disney World to Chicago. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$168FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$144FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$142FlexibilityNo cancel feeOn-time88%
DeltaCheapest$114Average$410FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$143Average$275FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$362FlexibilityNo cancel feeOn-time71%

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