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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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Walt Disney World to Chicago are usually found in February or April, booked 89 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap flight deals from Walt Disney World to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Walt Disney World (W9D) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$102
(eDestinos)

One-way from

$58
(Cheapflightsfares)

Popular in

June

Cheapest in

February

Average price

$211
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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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/16. 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 12/316:00 amMCO - ORD
1 stop14h 14mFrontier
Sat 1/46:10 amORD - MCO
1 stop13h 04mFrontier
Deal found 12/16$106
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/314:00 pmMCO - MDW
Nonstop2h 54mFrontier
Thu 1/27:17 amMDW - MCO
1 stop15h 52mFrontier
Deal found 12/17$179
This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/287:30 amSFB - RFD
Nonstop2h 54mAllegiant Air
Sat 1/410:14 amRFD - SFB
Nonstop2h 41mAllegiant Air
Deal found 12/17$197
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:25 amMCO - ORD
1 stop5h 39mMultiple Airlines
Mon 1/64:28 pmORD - MCO
1 stop6h 15mMultiple Airlines
Deal found 12/17$203
This FlightHub deal was found by Cheapflights users on 12/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3012:34 pmMCO - ORD
Nonstop3h 02mSpirit Airlines
Fri 1/38:14 pmORD - MCO
Nonstop3h 07mSpirit Airlines
Deal found 12/17$238
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:15 pmMCO - MDW
1 stop5h 51mDelta
Tue 12/319:30 amMDW - MCO
1 stop6h 29mDelta
Deal found 12/17$292
This Sun Country Air deal was found by Cheapflights users on 12/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/248:25 amMCO - ORD
1 stop25h 38mSun Country Air
Mon 12/307:30 pmORD - MCO
1 stop21h 46mSun Country Air
Deal found 12/17$305
This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/2412:40 pmMCO - ORD
1 stop5h 00mDelta
Tue 12/3110:30 amORD - MCO
1 stop5h 29mDelta
Deal found 12/16$356
This Mytrip deal was found by Cheapflights users on 12/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/218:00 amMCO - RFD
2 stops26h 17mMultiple Airlines
Mon 12/239:15 amRFD - MCO
2 stops23h 04mMultiple Airlines
Deal found 12/17$789

Find flights from Walt Disney World to Chicago within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 1/23

12:40 pm-10:27 pm

1 stop10h 47m

Chicago O'Hare Intl

Sun 1/26

10:59 am-2:51 pm

Nonstop2h 52m

$102

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 1/16

1:59 pm-4:10 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/19

6:06 pm-9:58 pm

Nonstop2h 52m

$104

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 1/24

8:00 am-9:52 am

Nonstop2h 52m

Chicago Greater Rockford

Mon 1/27

10:42 am-2:25 pm

Nonstop2h 43m

$107

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 1/18

4:56 pm-11:29 pm

1 stop7h 33m

Chicago Midway

Mon 1/20

4:41 pm-1:46 am

1 stop8h 05m

$108

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 1/8

7:30 pm-5:27 pm

1 stop22h 57m

Chicago O'Hare Intl

Tue 1/14

8:00 am-11:50 am

Nonstop2h 50m

$109

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/23

7:50 pm-9:45 pm

Nonstop2h 55m

Chicago Midway

Tue 1/28

1:20 pm-4:55 pm

Nonstop2h 35m

$164

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 1/6

1:30 pm-4:14 pm

1 stop27h 44m

Chicago Midway

Wed 1/8

6:52 pm-3:25 pm

1 stop19h 33m

$165

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 1/22

7:00 am-9:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sat 1/25

6:45 pm-10:35 pm

Nonstop2h 50m

$177

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 2/1

5:30 am-9:55 am

1 stop5h 25m

Chicago O'Hare Intl

Tue 2/4

2:55 pm-9:40 pm

1 stop5h 45m

$196

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 1/31

7:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Tue 2/4

10:57 am-5:15 pm

1 stop5h 18m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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.

Travel insights for flights from Walt Disney World to Chicago

Get recent, data-driven insights about flights from Walt Disney World to Chicago including ideal travel times, pricing trends, and more.

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 December 13, 2024.

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, September is the cheapest month in which you can book a flight from Walt Disney World to Chicago (average of $232). Flying from Walt Disney World to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

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 Tuesday evenings when fares are most often at their lowest. Tuesday 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 December 18, 2024.

The most flights from W9D to CHI are scheduled on a Wednesday (45 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 December 18, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Frontier and Delta 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
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 Frontier. Other airlines that offer cheap prices include Allegiant Air from $60 and Spirit Airlines from $77 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%), Southwest (97%), Brussels Airlines( 97%).

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

    Looking at all options, your cheapest flight can be booked for $59. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $104 on average our data indicates $1,274 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 $232). Flying from Walt Disney World to Chicago in June is currently the most expensive (average of $308). 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.

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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$41Average$154FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$154FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$120Average$195FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$147Average$332FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$151Average$312FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$155Average$339FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$454FlexibilityNo cancel feeOn-timeN/A
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