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$58+ 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 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in September or May, 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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$104
(Frontier)

One-way from

$58
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$188
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. 7% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Frontier deal was found by Cheapflights users on 4/22. 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.
Sun 5/256:10 amMCO - ORD
Nonstop3h 12mFrontier
Wed 5/285:03 pmORD - MCO
Nonstop2h 57mFrontier
Deal found 4/22$104
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 5/710:17 pmMCO - ORD
1 stop11h 38mSpirit Airlines
Sat 5/104:35 pmORD - MCO
Nonstop2h 45mSpirit Airlines
Deal found 4/23$106
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Tue 5/209:42 pmMCO - ORD
1 stop12h 08mMultiple Airlines
Wed 5/285:03 pmORD - MCO
Nonstop2h 57mMultiple Airlines
Deal found 4/22$107
This Mytrip deal was found by Cheapflights users on 4/23. 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 4/23$112
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 5/236:20 pmMCO - MDW
Nonstop2h 57mFrontier
Sat 5/319:12 pmMDW - MCO
Nonstop2h 45mFrontier
Deal found 4/23$117
This Southwest deal was found by Cheapflights users on 4/22. 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 5/288:15 pmMCO - MDW
Nonstop2h 50mSouthwest
Wed 6/47:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 4/22$197
This Delta deal was found by Cheapflights users on 4/22. 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 5/246:00 amMCO - ORD
1 stop7h 41mDelta
Sun 5/2510:30 amORD - MCO
1 stop7h 24mDelta
Deal found 4/22$199
This Delta deal was found by Cheapflights users on 4/22. 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 5/246:00 amMCO - MDW
1 stop7h 28mDelta
Sun 5/254:15 pmMDW - MCO
1 stop7h 09mDelta
Deal found 4/22$199
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Thu 5/226:17 amMCO - RFD
1 stop10h 09mMultiple Airlines
Sun 5/254:16 pmRFD - MCO
1 stop27h 27mMultiple Airlines
Deal found 4/23$216
This American Airlines deal was found by Cheapflights users on 4/23. 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 7/36:00 amMCO - ORD
Nonstop3h 12mAmerican Airlines
Sun 7/66:00 amORD - MCO
1 stop6h 12mAmerican Airlines
Deal found 4/23$218
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/212:25 pmMCO - ORD
Nonstop3h 10mUnited Airlines
Mon 5/267:10 amORD - MCO
Nonstop2h 54mUnited Airlines
Deal found 4/22$227
This JetBlue deal was found by Cheapflights users on 4/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:20 amMCO - ORD
1 stop9h 44mJetBlue
Fri 5/304:03 pmORD - MCO
1 stop6h 50mJetBlue
Deal found 4/22$248

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 April 24, 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

Sun 5/25

6:10 am-8:22 am

Nonstop3h 12m

Chicago O'Hare Intl

Wed 5/28

5:03 pm-9:00 pm

Nonstop2h 57m

$104

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/14

10:17 pm-8:55 am

1 stop11h 38m

Chicago O'Hare Intl

Sat 5/17

4:15 pm-8:18 pm

Nonstop3h 03m

$105

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/7

10:17 pm-8:55 am

1 stop11h 38m

Chicago O'Hare Intl

Sat 5/10

4:35 pm-8:20 pm

Nonstop2h 45m

$106

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

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 5/23

6:20 pm-8:17 pm

Nonstop2h 57m

Chicago Midway

Sat 5/31

9:12 pm-12:57 am

Nonstop2h 45m

$117

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 5/28

8:15 pm-10:05 pm

Nonstop2h 50m

Chicago Midway

Wed 6/4

7:55 pm-11:30 pm

Nonstop2h 35m

$197

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 5/24

2:00 pm-6:48 pm

1 stop5h 48m

Chicago O'Hare Intl

Sun 5/25

10:30 am-6:54 pm

1 stop7h 24m

$199

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/24

6:00 am-12:28 pm

1 stop7h 28m

Chicago Midway

Sun 5/25

4:15 pm-12:24 am

1 stop7h 09m

$199

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Thu 5/22

6:17 am-3:26 pm

1 stop10h 09m

Chicago Greater Rockford

Sun 5/25

4:16 pm-8:43 pm

1 stop27h 27m

$216

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 7/4

6:05 am-8:17 am

Nonstop3h 12m

Chicago O'Hare Intl

Sun 7/6

6:57 am-1:12 pm

1 stop5h 15m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 29 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 April 18, 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 April 24, 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 April 24, 2025.

The most flights from W9D to CHI are scheduled on a Tuesday (62 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (42 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 April 24, 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
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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 $58 on Spirit Airlines. Other airlines that offer cheap prices include Allegiant Air from $60 and Frontier from $60 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 (95%), Azul (90%), ANA( 89%).

  • 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 $80 on average our data indicates $995 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$153FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$163FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$100Average$198FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$155Average$348FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$351FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$323FlexibilityNo cancel feeOn-time69%
DeltaCheapest$196Average$430FlexibilityNo cancel feeOn-timeN/A

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