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$62+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
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 March 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:30 am
MCO
-
MDW
Nonstop2h 56m
Frontier
Sun 4/262:00 pm
MDW
-
MCO
Nonstop2h 48m
Frontier
Deal found 3/19$106
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:00 pm
MCO
-
ORD
Nonstop3h 23m
Frontier
Wed 5/63:55 pm
ORD
-
MCO
Nonstop2h 56m
Frontier
Deal found 3/20$107
This Expedia deal was found by Cheapflights users on 3/21. 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.
Sat 5/21:00 pm
MCO
-
ORD
Nonstop3h 23m
Frontier
Sat 5/95:30 pm
ORD
-
MCO
Nonstop3h 02m
Frontier
Deal found 3/21$108
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/1612:45 pm
MCO
-
ORD
Nonstop3h 23m
Frontier
Sat 4/188:00 am
ORD
-
MCO
Nonstop2h 54m
Frontier
Deal found 3/17$111
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:30 am
MCO
-
MDW
Nonstop2h 56m
Frontier
Sat 4/259:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 3/19$111
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:48 pm
MCO
-
ORD
Nonstop3h 21m
Frontier
Sat 4/188:00 am
ORD
-
MCO
Nonstop2h 54m
Frontier
Deal found 3/18$112
This Super.com deal was found by Cheapflights users on 3/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:00 pm
MCO
-
ORD
Nonstop3h 23m
Frontier
Mon 4/276:00 am
ORD
-
MCO
Nonstop2h 57m
Frontier
Deal found 3/19$113
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:00 pm
MCO
-
ORD
Nonstop3h 23m
Frontier
Sun 4/266:00 am
ORD
-
MCO
Nonstop2h 57m
Frontier
Deal found 3/19$115
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/182:00 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Sat 4/259:14 am
MDW
-
MCO
Nonstop2h 49m
Frontier
Deal found 3/20$116
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 4/172:48 pm
MCO
-
ORD
Nonstop3h 21m
Frontier
Mon 4/206:00 am
ORD
-
MCO
Nonstop2h 57m
Frontier
Deal found 3/17$117
This Frontier deal was found by Cheapflights users on 3/17. 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.
Fri 4/172:48 pm
MCO
-
ORD
Nonstop3h 21m
Frontier
Sun 4/266:00 am
ORD
-
MCO
Nonstop2h 57m
Frontier
Deal found 3/17$118
This Priceline deal was found by Cheapflights users on 3/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:00 am
MCO
-
ORD
Nonstop3h 05m
Multiple Airlines
Sat 4/258:00 am
ORD
-
MCO
Nonstop2h 54m
Multiple Airlines
Deal found 3/19$119

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 March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Kiwi.com)

One-way from

$62
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$181
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 ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 22, 2026.
Use the filters below to find and compare flights from Bay Lake to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 5/8

8:05 am-9:59 am

Nonstop2h 54m

Chicago Greater Rockford

Fri 5/15

10:49 am-2:22 pm

Nonstop2h 33m

$142

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 5/1

8:00 am-9:54 am

Nonstop2h 54m

Chicago Greater Rockford

Fri 5/8

10:49 am-2:22 pm

Nonstop2h 33m

$143

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 5/22

5:22 pm-7:13 pm

Nonstop2h 51m

Chicago Greater Rockford

Fri 5/29

8:03 pm-11:37 pm

Nonstop2h 34m

$159

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 5/8

8:05 am-9:59 am

Nonstop2h 54m

Chicago Greater Rockford

Mon 5/11

10:49 am-2:22 pm

Nonstop2h 33m

$169
Quickest round-trip

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 6/3

7:30 am-9:17 am

Nonstop2h 47m

Chicago Greater Rockford

Fri 6/12

7:53 pm-11:28 pm

Nonstop2h 35m

$191

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Mon 6/1

5:22 pm-7:13 pm

Nonstop2h 51m

Chicago Greater Rockford

Mon 6/8

7:53 pm-11:28 pm

Nonstop2h 35m

$200

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Sat 4/18

10:49 pm-9:47 am

1 stop11h 58m

Chicago Greater Rockford

Mon 4/20

7:09 pm-1:34 pm

2 stops17h 25m

$205

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 4/17

8:00 am-9:54 am

Nonstop2h 54m

Chicago Greater Rockford

Mon 4/20

10:44 am-2:17 pm

Nonstop2h 33m

$205

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Mon 4/20

8:00 am-9:54 am

Nonstop2h 54m

Chicago Greater Rockford

Mon 4/27

10:44 am-2:17 pm

Nonstop2h 33m

$220

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 4/17

8:00 am-9:54 am

Nonstop2h 54m

Chicago Greater Rockford

Mon 7/13

7:50 pm-11:29 pm

Nonstop2h 39m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 60 resultsSorted by cheapest first
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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 March 13, 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, September is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $46). 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 March 22, 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 23% 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 March 14, 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 evenings 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 March 22, 2026.

The most flights from W9D to CHI are scheduled on a Saturday (87 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (43 on average).

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 March 22, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
4,324 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,455 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,487 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,531 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,019 reviews
Southwest
8.0
Very good
4,324 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 Allegiant Air. Other airlines that offer cheap prices include Frontier from $41 and Spirit Airlines from $47 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: ANA (86%), Azul (80%), Japan Airlines( 79%).

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

    Looking at all options, your cheapest flight can be booked for $71. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $107 on average, our data indicates $963 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, September is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $46). 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 8 airlines flying from Walt Disney World to Chicago

Discover the top 8 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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$167FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$156FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$172FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$392FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$146Average$328FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$148Average$280FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$153Average$305FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$314FlexibilityNo cancel feeOn-time71%

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