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$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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Find cheap flights from Walt Disney World to Chicago with Cheapflights

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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 February 5, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/58:20 am
MCO
-
ORD
Nonstop3h 26m
Frontier
Tue 3/104:18 pm
ORD
-
MCO
Nonstop3h 05m
Frontier
Deal found 2/3$76
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 2/205:47 pm
MCO
-
ORD
Nonstop3h 25m
Frontier
Tue 2/248:30 am
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 2/4$77
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:23 pm
MCO
-
ORD
Nonstop3h 15m
Frontier
Sun 3/84:18 pm
ORD
-
MCO
Nonstop3h 05m
Frontier
Deal found 2/1$78
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:23 pm
MCO
-
ORD
Nonstop3h 15m
Multiple Airlines
Mon 3/98:16 pm
ORD
-
MCO
1 stop10h 23m
Multiple Airlines
Deal found 2/2$79
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:33 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
Fri 3/64:23 pm
ORD
-
MCO
Nonstop3h 05m
Frontier
Deal found 2/3$80
This Frontier deal was found by Cheapflights users on 1/31. 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 2/141:16 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
Tue 2/178:30 am
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 1/31$81
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:23 pm
MCO
-
ORD
Nonstop3h 15m
Multiple Airlines
Tue 3/104:43 pm
ORD
-
MCO
1 stop6h 11m
Multiple Airlines
Deal found 2/2$82
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:33 pm
MCO
-
ORD
Nonstop3h 19m
Multiple Airlines
Sat 3/78:16 pm
ORD
-
MCO
1 stop9h 23m
Multiple Airlines
Deal found 2/1$83
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/252:50 pm
MCO
-
ORD
1 stop7h 23m
Multiple Airlines
Wed 3/48:30 am
ORD
-
MCO
Nonstop2h 56m
Multiple Airlines
Deal found 2/2$84
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Wed 3/41:33 pm
MCO
-
ORD
Nonstop3h 19m
Multiple Airlines
Sun 3/810:44 am
ORD
-
MCO
Nonstop2h 50m
Multiple Airlines
Deal found 2/2$85
This Frontier deal was found by Cheapflights users on 2/1. 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.
Sat 5/22:13 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Sat 5/99:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 2/1$86
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/281:24 pm
MCO
-
ORD
1 stop10h 53m
Frontier
Tue 3/38:30 am
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 2/1$87

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$76
(Cheapflightsfares)

One-way from

$49
(Expedia)

Popular in

June

Cheapest in

September

Average price

$151
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 ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 5, 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 - ORD

MCOORD

Orlando

Sat 3/7

5:34 pm-7:47 pm

Nonstop3h 13m

Chicago O'Hare Intl

Mon 3/9

8:16 pm-7:39 am

1 stop10h 23m

$109

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 3/6

9:23 pm-11:38 pm

Nonstop3h 15m

Chicago O'Hare Intl

Sun 3/8

8:16 pm-7:39 am

1 stop10h 23m

$110

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 3/4

10:28 am-7:07 pm

1 stop9h 39m

Chicago Midway

Sat 3/7

6:15 am-10:05 am

Nonstop2h 50m

$113

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 2/19

5:34 pm-7:47 pm

Nonstop3h 13m

Chicago O'Hare Intl

Mon 2/23

10:44 am-2:34 pm

Nonstop2h 50m

$124

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 3/13

2:50 pm-4:56 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 3/15

9:30 am-1:16 pm

Nonstop2h 46m

$151

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 3/18

6:00 am-11:17 am

1 stop6h 17m

Chicago O'Hare Intl

Wed 3/25

9:45 am-7:27 pm

1 stop8h 42m

$151

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 4/9

11:09 am-6:35 pm

1 stop8h 26m

Chicago O'Hare Intl

Mon 4/13

4:36 pm-11:50 pm

1 stop6h 14m

$161

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 4/1

12:05 pm-1:59 pm

Nonstop2h 54m

Chicago Greater Rockford

Wed 4/8

5:46 pm-9:19 pm

Nonstop2h 33m

$169

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 2/23

5:01 am-5:04 pm

1 stop13h 03m

Chicago O'Hare Intl

Fri 2/27

3:11 pm-7:07 pm

Nonstop2h 56m

$172

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 3/7

8:40 pm-10:57 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 3/9

5:50 pm-9:40 pm

Nonstop2h 50m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

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 January 30, 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 $43). 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 February 5, 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 34% 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 31, 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 February 5, 2026.

The most flights from W9D to CHI are scheduled on a Wednesday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 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 February 5, 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
4,274 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

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
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

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.
United Airlines
7.4
Good
9,236 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

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.
American Airlines
7.2
Good
11,222 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

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
8,411 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

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
5.7
Fair
3,052 reviews
Southwest
8.0
Very good
4,274 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

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.

  • How long is the flight from Walt Disney World to Chicago?

    Departing from Walt Disney World to Chicago will take you 2h 54m. The distance from Walt Disney World to Chicago 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 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 Spirit Airlines from $44 and Allegiant Air from $44 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: Austrian Airlines (87%), Royal Jordanian (81%), Cathay Pacific( 80%).

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

    Looking at all options, your cheapest flight can be booked for $60. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $72 on average, our data indicates $968 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 $43). 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

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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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$153FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$152FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$152FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$368FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$145Average$280FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$150Average$305FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$356FlexibilityNo cancel feeOn-time71%

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