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$52+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in September or January, booked 86 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 November 5, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$78
(Frontier)

One-way from

$52
(FlightHub)

Popular in

June

Cheapest in

September

Average price

$208
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
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From Walt Disney World to Chicago (CHI)
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One-way flight from Walt Disney World to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 5, 2025.

This Frontier deal was found by Cheapflights users on 11/5. 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.
Thu 12/257:46 amMCO - ORD
Nonstop3h 32mFrontier
Fri 1/210:12 amORD - MCO
Nonstop2h 55mFrontier
Deal found 11/5$78
This Priceline deal was found by Cheapflights users on 11/4. 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.
Sun 12/217:04 pmMCO - MDW
Nonstop3h 00mFrontier
Sun 1/1110:18 amMDW - MCO
Nonstop2h 46mFrontier
Deal found 11/4$78
This Priceline deal was found by Cheapflights users on 11/4. 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.
Tue 11/259:00 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Thu 11/276:23 pmORD - MCO
Nonstop3h 04mMultiple Airlines
Deal found 11/4$79
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Fri 11/219:33 pmMCO - MDW
Nonstop2h 56mFrontier
Thu 11/275:30 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$79
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/511:00 amMCO - ORD
Nonstop3h 16mMultiple Airlines
Tue 12/912:09 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Deal found 11/4$80
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 11/215:15 amMCO - ORD
Nonstop3h 11mFrontier
Mon 11/246:15 pmORD - MCO
Nonstop3h 04mFrontier
Deal found 11/4$81
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Fri 11/219:33 pmMCO - MDW
Nonstop2h 56mFrontier
Mon 11/245:47 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$81
This Expedia deal was found by Cheapflights users on 11/4. 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.
Tue 12/29:00 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Tue 12/912:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Deal found 11/4$82
This Super.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/48:40 amMCO - ORD
1 stop5h 28mFrontier
Sun 12/72:36 pmORD - MCO
Nonstop3h 05mFrontier
Deal found 11/5$83
This Frontier deal was found by Cheapflights users on 11/4. 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.
Thu 12/412:57 pmMCO - MDW
1 stop10h 15mFrontier
Mon 12/83:10 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 11/4$84
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/209:00 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Tue 12/24:58 pmORD - MCO
Nonstop2h 44mSpirit Airlines
Deal found 11/5$85
This Gotogate deal was found by Cheapflights users on 11/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:40 pmMCO - MDW
Nonstop2h 59mFrontier
Mon 12/83:52 pmMDW - MCO
1 stop6h 49mFrontier
Deal found 11/4$85

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 November 5, 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 12/5

8:00 am-9:48 am

Nonstop2h 48m

Chicago Greater Rockford

Mon 12/8

10:38 am-2:15 pm

Nonstop2h 37m

$93

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 11/25

9:00 pm-11:06 pm

Nonstop3h 06m

Chicago O'Hare Intl

Fri 11/28

6:48 am-10:30 am

Nonstop2h 42m

$100

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 11/21

1:56 pm-4:03 pm

Nonstop3h 07m

Chicago O'Hare Intl

Mon 11/24

6:48 am-10:30 am

Nonstop2h 42m

$100

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 11/26

7:40 am-9:27 am

Nonstop2h 47m

Chicago Greater Rockford

Sat 12/6

1:38 pm-5:15 pm

Nonstop2h 37m

$118

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 11/14

2:44 pm-4:28 pm

Nonstop2h 44m

Chicago Greater Rockford

Mon 11/17

5:18 pm-8:47 pm

Nonstop2h 29m

$136

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 1/30

9:05 am-11:10 am

Nonstop3h 05m

Chicago O'Hare Intl

Tue 2/3

3:45 pm-7:30 pm

Nonstop2h 45m

$137

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 1/16

4:40 pm-6:45 pm

Nonstop3h 05m

Chicago O'Hare Intl

Sun 1/18

7:20 am-11:15 am

Nonstop2h 55m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 1/30

7:05 pm-9:00 pm

Nonstop2h 55m

Chicago Midway

Tue 2/3

7:35 am-11:20 am

Nonstop2h 45m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 1/7

2:35 pm-4:30 pm

Nonstop2h 55m

Chicago Midway

Sun 1/11

6:00 pm-9:40 pm

Nonstop2h 40m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 11/22

6:05 pm-11:42 am

2 stops18h 37m

Chicago Midway

Mon 12/8

3:10 pm-6:58 pm

Nonstop2h 48m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 59 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 October 31, 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, March is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $41). Flying from Walt Disney World to Chicago in June is currently the most expensive (average of $107). 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 November 5, 2025.

One of the essential ways to save on airfare from Walt Disney World to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 46% on airfare.

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 Wednesday evenings when fares are most often at their lowest. Sunday mornings 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 November 5, 2025.

The most flights from W9D to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Sunday, 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 November 5, 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
4,240 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
9,002 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
11,042 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
8,115 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
3,116 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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 48m. 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 $55 and United Airlines from $69 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: ITA Airways (97%), Austrian Airlines (92%), Spirit Airlines( 90%).

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

    Looking at all options, your cheapest flight can be booked for $43. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $61 on average, our data indicates $1,105 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, March is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $41). Flying from Walt Disney World to Chicago in June is currently the most expensive (average of $107). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$163FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$74Average$145FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$82Average$162FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$373FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$143Average$278FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$310FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$363FlexibilityNo cancel feeOn-time71%

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