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$57+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in September or August, booked 89 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 July 3, 2025.

Round-trip from

$102
(FlightHub)

One-way from

$57
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$173
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 ($13 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 July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/183:49 pmMCO - ORD
Nonstop3h 09mSpirit Airlines
Tue 7/224:36 pmORD - MCO
Nonstop2h 47mSpirit Airlines
Deal found 7/2$102
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Fri 9/197:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 9/219:48 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 7/3$102
This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/258:23 pmMCO - ORD
Nonstop2h 59mMultiple Airlines
Sat 8/306:00 amORD - MCO
1 stop5h 22mMultiple Airlines
Deal found 7/3$103
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1911:07 amMCO - ORD
1 stop5h 03mFrontier
Sun 8/247:46 pmORD - MCO
Nonstop3h 06mFrontier
Deal found 7/2$104
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/126:30 amSFB - RFD
Nonstop2h 42mAllegiant Air
Fri 7/188:04 pmRFD - SFB
Nonstop2h 35mAllegiant Air
Deal found 7/2$105
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:36 pmMCO - RFD
2 stops19h 40mMultiple Airlines
Fri 9/510:37 amRFD - MCO
1 stop11h 25mMultiple Airlines
Deal found 7/1$234

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 July 3, 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

MCO - ORD

MCOORD

Orlando

Fri 7/18

3:49 pm-5:58 pm

Nonstop3h 09m

Chicago O'Hare Intl

Tue 7/22

4:36 pm-8:23 pm

Nonstop2h 47m

$102

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sun 9/21

9:48 am-1:28 pm

Nonstop2h 40m

$102

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 8/25

8:23 pm-10:22 pm

Nonstop2h 59m

Chicago O'Hare Intl

Sat 8/30

6:00 am-12:22 pm

1 stop5h 22m

$103

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 8/19

11:07 am-3:10 pm

1 stop5h 03m

Chicago O'Hare Intl

Sun 8/24

7:46 pm-11:52 pm

Nonstop3h 06m

$104

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Sat 7/12

6:30 am-8:12 am

Nonstop2h 42m

Chicago Greater Rockford

Fri 7/18

8:04 pm-11:39 pm

Nonstop2h 35m

$105

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Sat 8/30

7:36 pm-2:16 pm

2 stops19h 40m

Chicago Greater Rockford

Fri 9/5

10:37 am-11:02 pm

1 stop11h 25m

$234

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 8/6

9:15 am-10:57 am

Nonstop2h 42m

$57

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 7/22

9:59 pm-7:04 am

1 stop10h 05m

$57

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/21

12:12 pm-5:05 pm

1 stop5h 53m

$57

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 9/5

1:20 pm-10:43 pm

1 stop10h 23m

$58

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 16 results
1
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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 June 27, 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 89 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 July 3, 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 Friday 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 July 3, 2025.

The most flights from W9D to CHI are scheduled on a Thursday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Allegiant Air 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
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

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
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

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.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

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.
Allegiant Air
7.2
Good
709 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

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
8,094 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

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
5.9
Fair
3,284 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

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.

  • 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 $57 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $57 and Allegiant Air from $58 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 (95%), Austrian Airlines (94%), SWISS( 89%).

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

    Looking at all options, your cheapest flight can be booked for $63. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $86 on average our data indicates $2,335 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 Bay Lake?

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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$60Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$158FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$164FlexibilityNo cancel feeOn-time88%
DeltaCheapest$138Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$327FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$356FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$160Average$324FlexibilityNo cancel feeOn-time63%

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