HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$49+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
feb. 19 — feb. 261
jue. 2/19
jue. 2/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Walt Disney World to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in September or February, 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

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 enero 20, 2026.

This Super.com deal was found by Cheapflights users on 1/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/253:39 pm
MCO
-
ORD
Nonstop3h 07m
Spirit Airlines
sáb. 2/2812:44 pm
ORD
-
MCO
Nonstop2h 47m
Spirit Airlines
Deal found 1/18$84
This CheapOair deal was found by Cheapflights users on 1/19. 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.
mar. 2/245:34 pm
MCO
-
ORD
Nonstop3h 13m
Spirit Airlines
sáb. 2/2810:44 am
ORD
-
MCO
Nonstop2h 50m
Spirit Airlines
Deal found 1/19$85
This Super.com deal was found by Cheapflights users on 1/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/111:33 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
mié. 2/188:30 am
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 1/18$86
This Super.com deal was found by Cheapflights users on 1/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/53:43 pm
MCO
-
ORD
Nonstop3h 09m
Spirit Airlines
dom. 2/810:48 am
ORD
-
MCO
Nonstop2h 50m
Spirit Airlines
Deal found 1/20$88
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
mié. 2/181:33 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
lun. 2/233:50 pm
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 1/18$90
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/253:39 pm
MCO
-
ORD
Nonstop3h 07m
Spirit Airlines
mar. 3/310:44 am
ORD
-
MCO
Nonstop2h 50m
Spirit Airlines
Deal found 1/20$91
This CheapOair deal was found by Cheapflights users on 1/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/181:33 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
mié. 2/258:30 am
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 1/18$92
This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/68:09 am
MCO
-
ORD
Nonstop3h 26m
Multiple Airlines
dom. 2/810:48 am
ORD
-
MCO
Nonstop2h 50m
Multiple Airlines
Deal found 1/20$93
This Cheapflightsfares deal was found by Cheapflights users on 1/19. 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.
sáb. 2/145:34 pm
MCO
-
ORD
Nonstop3h 13m
Spirit Airlines
mar. 2/1712:44 pm
ORD
-
MCO
Nonstop2h 47m
Spirit Airlines
Deal found 1/19$94
This CheapOair deal was found by Cheapflights users on 1/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/285:34 pm
MCO
-
ORD
Nonstop3h 13m
Spirit Airlines
mar. 3/310:44 am
ORD
-
MCO
Nonstop2h 50m
Spirit Airlines
Deal found 1/18$95
This eDestinos deal was found by Cheapflights users on 1/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/41:33 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
vie. 3/64:23 pm
ORD
-
MCO
Nonstop3h 05m
Frontier
Deal found 1/19$96
This Super.com deal was found by Cheapflights users on 1/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/65:49 pm
MCO
-
MDW
Nonstop3h 03m
Frontier
dom. 2/81:00 pm
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 1/20$96

Find 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 enero 20, 2026.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$84
(Super.com)

One-way from

$49
(Frontier)

Popular in

June

Cheapest in

September

Average price

$164
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
Search Deals
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. 12% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 enero 20, 2026.
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 - MDW

MCOMDW

Orlando

vie. 2/20

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

dom. 2/22

7:30 am-11:20 am

Nonstop2h 50m

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

lun. 3/16

11:05 am-1:08 pm

Nonstop3h 03m

Chicago Midway

mar. 3/24

11:19 am-3:04 pm

Nonstop2h 45m

$114

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

sáb. 2/14

12:49 pm-2:55 pm

Nonstop3h 06m

Chicago Midway

sáb. 2/21

9:15 am-8:47 pm

1 stop10h 32m

$115

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

mar. 2/24

10:28 am-7:07 pm

1 stop9h 39m

Chicago Midway

mié. 3/4

7:15 am-3:04 pm

1 stop6h 49m

$130

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

jue. 2/19

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

dom. 2/22

7:30 am-11:20 am

Nonstop2h 50m

$133

OrlandoChicago

MCO - ORD

MCOORD

Orlando

mié. 2/18

10:58 am-1:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

mié. 2/18

3:41 pm-7:31 pm

Nonstop2h 50m

$152

OrlandoChicago

MCO - ORD

MCOORD

Orlando

dom. 2/1

8:45 am-11:11 am

Nonstop3h 26m

Chicago O'Hare Intl

dom. 2/8

10:15 am-2:09 pm

Nonstop2h 54m

$155

OrlandoChicago

MCO - ORD

MCOORD

Orlando

mié. 2/25

7:10 am-9:28 am

Nonstop3h 18m

Chicago O'Hare Intl

sáb. 2/28

6:00 am-9:46 am

Nonstop2h 46m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 2/13

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

dom. 2/15

7:30 am-11:20 am

Nonstop2h 50m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

mié. 3/4

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

lun. 3/9

3:45 pm-7:20 pm

Nonstop2h 35m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 60 results
1
2
3
...
6

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 January 16, 2026.

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 $42). 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 enero 20, 2026.

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 36% 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 January 17, 2026.

Travelers seeking maximum savings on their Walt Disney World to Chicago flight should consider departing on Sunday afternoons 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 enero 20, 2026.

The most flights from W9D to CHI are scheduled on a Monday (73 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 enero 20, 2026.
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
4,266 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
9,188 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
11,169 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
8,359 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

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 3h 01m. 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 $39 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $44 and Spirit Airlines from $45 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: Cathay Pacific (87%), Royal Jordanian (82%), Austrian Airlines( 81%).

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

    Looking at all options, your cheapest flight can be booked for $65. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $84 on average, our data indicates $919 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 $42). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Walt Disney World to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to Midway flights
West Palm Beach to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Fort Lauderdale to Midway flights
Miami to Midway flights
Tampa to Midway flights
Orlando to St. Louis flights
Fort Myers to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Pensacola to O'Hare Intl flights
West Palm Beach to Midway flights
Tampa to St. Louis flights
Fort Myers to Midway flights
Fort Lauderdale to St. Louis flights
Jacksonville to Midway flights
Miami to St. Louis flights
Sarasota to St. Louis flights
Fort Myers to St. Louis flights
Jacksonville to St. Louis flights
Panama City to O'Hare Intl flights
Sarasota to Midway flights
West Palm Beach to St. Louis flights
Orlando Sanford Intl to Rockford flights
Valparaiso to O'Hare Intl flights
Pensacola to St. Louis flights
Tampa to Moline flights
Key West to O'Hare Intl flights
Pensacola to Midway flights
Panama City to Midway flights
St Petersburg to Rockford flights
Panama City to St. Louis flights
Fort Lauderdale to Peoria flights
Orlando to Moline flights
Tampa to Peoria flights
Daytona Beach to O'Hare Intl flights
Gainesville to Midway flights
Jacksonville to Peoria flights
Orlando to Peoria flights
Fort Myers to Moline flights
Fort Lauderdale to Moline flights
Fort Lauderdale to Rockford flights
Melbourne to St. Louis flights
Sarasota to Moline flights
Tallahassee to O'Hare Intl flights
Gainesville to O'Hare Intl flights
West Palm Beach to Moline flights

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 enero 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$159FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$152FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$152FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$368FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$145Average$279FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$149Average$304FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$358FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.