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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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in April or May, booked 76 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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$90
(FlightHub)

One-way from

$52
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$217
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. 11% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This FlightHub deal was found by Cheapflights users on 3/30. 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.
Tue 4/88:54 amMCO - ORD
Nonstop3h 15mSpirit Airlines
Sun 4/138:45 amORD - MCO
Nonstop2h 47mSpirit Airlines
Deal found 3/30$90
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 4/116:00 amMCO - ORD
Nonstop3h 04mMultiple Airlines
Mon 4/149:50 amORD - MCO
Nonstop2h 56mMultiple Airlines
Deal found 3/30$96
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Fri 5/163:08 pmSFB - RFD
Nonstop2h 43mAllegiant Air
Mon 5/195:41 pmRFD - SFB
Nonstop2h 30mAllegiant Air
Deal found 3/30$97
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 5/159:23 pmMCO - ORD
Nonstop3h 09mFrontier
Mon 5/194:15 pmORD - MCO
Nonstop3h 03mFrontier
Deal found 3/30$98
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Tue 4/89:25 pmMCO - MDW
Nonstop2h 59mFrontier
Sun 4/1310:19 amMDW - MCO
Nonstop2h 50mFrontier
Deal found 3/30$102
This Southwest deal was found by Cheapflights users on 3/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/95:25 pmMCO - MDW
Nonstop3h 00mSouthwest
Tue 7/155:20 pmMDW - MCO
Nonstop2h 45mSouthwest
Deal found 3/30$181
This Southwest deal was found by Cheapflights users on 3/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/711:00 amMCO - ORD
Nonstop3h 05mSouthwest
Mon 5/126:00 amORD - MCO
Nonstop2h 40mSouthwest
Deal found 3/30$197
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/297:15 pmMCO - ORD
Nonstop3h 07mAmerican Airlines
Tue 6/36:38 pmORD - MCO
Nonstop2h 50mAmerican Airlines
Deal found 3/31$209
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/237:52 pmMCO - ORD
1 stop5h 06mDelta
Tue 5/273:57 pmORD - MCO
1 stop7h 27mDelta
Deal found 3/30$229
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/195:30 amMCO - MDW
1 stop7h 25mDelta
Tue 7/221:00 pmMDW - MCO
1 stop5h 23mDelta
Deal found 3/31$229
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Wed 4/301:51 pmMCO - RFD
1 stop31h 55mMultiple Airlines
Mon 5/58:58 amRFD - MCO
3 stops23h 28mMultiple Airlines
Deal found 3/30$361

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 31, 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

Thu 4/10

6:00 am-8:04 am

Nonstop3h 04m

Chicago O'Hare Intl

Sat 4/12

11:45 am-3:31 pm

Nonstop2h 46m

$90

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 4/11

6:00 am-8:04 am

Nonstop3h 04m

Chicago O'Hare Intl

Mon 4/14

9:50 am-1:46 pm

Nonstop2h 56m

$96

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 5/16

3:08 pm-4:51 pm

Nonstop2h 43m

Chicago Greater Rockford

Mon 5/19

5:41 pm-9:11 pm

Nonstop2h 30m

$97

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 5/15

9:23 pm-11:32 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 5/19

4:15 pm-8:18 pm

Nonstop3h 03m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 4/8

9:25 pm-11:24 pm

Nonstop2h 59m

Chicago Midway

Sun 4/13

10:19 am-2:09 pm

Nonstop2h 50m

$102

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 4/29

6:25 pm-8:15 pm

Nonstop2h 50m

Chicago Midway

Tue 5/6

8:30 am-1:55 pm

1 stop4h 25m

$189

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/7

11:00 am-1:05 pm

Nonstop3h 05m

Chicago O'Hare Intl

Mon 5/12

6:00 am-9:40 am

Nonstop2h 40m

$197

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/28

6:50 pm-11:58 pm

1 stop6h 08m

Chicago O'Hare Intl

Wed 6/4

1:30 pm-7:48 pm

1 stop5h 18m

$201

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 5/29

7:15 pm-9:22 pm

Nonstop3h 07m

Chicago O'Hare Intl

Tue 6/3

11:35 am-3:16 pm

Nonstop2h 41m

$209

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 5/24

12:16 pm-2:23 pm

Nonstop3h 07m

Chicago O'Hare Intl

Mon 5/26

7:10 am-11:04 am

Nonstop2h 54m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 26 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 March 28, 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 76 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 $323). 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 31, 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 Wednesday 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 March 31, 2025.

The most flights from W9D to CHI are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Walt Disney World to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

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
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

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.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

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
8,614 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

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.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

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
10,000 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

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.

  • 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 Frontier. Other airlines that offer cheap prices include Spirit Airlines from $60 and Allegiant Air from $75 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: Japan Airlines (98%), Cathay Pacific (98%), Frontier( 97%).

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

    Looking at all options, your cheapest flight can be booked for $55. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $90 on average our data indicates $2,357 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$151FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$158FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$109Average$196FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$155Average$352FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$156Average$317FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$156Average$349FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$430FlexibilityNo cancel feeOn-timeN/A
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