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$31+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Nov 10 — Nov 171
Sun 11/10
Sun 11/17
1 adult, Economy
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The best prices from Walt Disney World to Chicago are usually found in February or April, booked 76 days in advance, depart on a Saturday or Friday 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 November 5, 2024.

Popular in

June

Cheapest in

February

Round-trip from

$75
(Cheapflightsfares)

One-way from

$31
(eDestinos)
High demand for flights, 28% potential price rise
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Best time to find cheap flights, 30% potential price drop
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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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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 November 5, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 12/45:02 amMCO - ORD
1 stop12h 04mSpirit Airlines
Tue 12/101:13 pmORD - MCO
Nonstop3h 03mSpirit Airlines
Deal found 11/5$98
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/46:11 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Mon 12/910:59 amORD - MCO
Nonstop2h 55mMultiple Airlines
Deal found 11/4$99
This Flightnetwork deal was found by Cheapflights users on 11/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/145:28 pmMCO - ORD
Nonstop3h 15mFrontier
Mon 11/188:26 pmORD - MCO
Nonstop3h 03mFrontier
Deal found 11/4$100
This Flightnetwork deal was found by Cheapflights users on 11/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/146:00 amMCO - MDW
Nonstop2h 55mFrontier
Mon 11/188:20 pmMDW - MCO
Nonstop2h 56mFrontier
Deal found 11/4$100
This Gotogate deal was found by Cheapflights users on 11/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/158:05 amSFB - RFD
Nonstop2h 47mAllegiant Air
Mon 11/1810:42 amRFD - SFB
Nonstop2h 33mAllegiant Air
Deal found 11/4$112
This Southwest deal was found by Cheapflights users on 11/5. 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.
Tue 12/37:10 amMCO - MDW
Nonstop2h 55mSouthwest
Tue 12/1011:55 amMDW - MCO
1 stop5h 10mSouthwest
Deal found 11/5$259
This FareScan deal was found by Cheapflights users on 11/3. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/238:30 pmMCO - RFD
1 stop17h 28mMultiple Airlines
Sat 11/3012:13 pmRFD - MCO
2 stops19h 16mMultiple Airlines
Deal found 11/3$633

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 12/5

5:34 pm-11:51 pm

1 stop7h 17m

$53

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 11/14

6:05 pm-8:15 pm

Nonstop3h 10m

$54

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 11/15

8:05 am-9:52 am

Nonstop2h 47m

$76

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 2/1

7:15 am-9:21 am

Nonstop3h 06m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 1/8

7:10 am-9:05 am

Nonstop2h 55m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 11/18

8:34 pm-10:38 am

2 stops15h 04m

$81

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 12/7

5:30 am-10:46 am

1 stop6h 16m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 2/25

5:15 am-10:09 am

1 stop5h 54m

$53

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 11/27

1:29 pm-8:21 am

1 stop19h 52m

$138

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 11/12

7:00 am-9:13 am

Nonstop3h 13m

$149

Flights are sorted by cheapest first

Deals found on 11/5

Showing 1-10 of 27 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 November 1, 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 76 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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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 November 5, 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 November 3, 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.

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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 November 5, 2024.

The most flights from W9D to CHI are scheduled on a Tuesday (42 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (19 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 November 5, 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
5,082 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Porter Airlines
7.8
Good
292 reviews
Southwest
8.1
Very good
5,082 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,215 reviews
Southwest
8.1
Very good
5,082 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
863 reviews
Southwest
8.1
Very good
5,082 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

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.

  • Can I find flights from Walt Disney World to Chicago for under $100 on Cheapflights?

    Yes, there are multiple flights from Walt Disney World to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $75, but on average you can expect to pay $193.

  • Are there nonstop flights from Walt Disney World to Chicago for under $100 on Cheapflights?

    Cheapflights has at least 8 direct flights from Walt Disney World to Chicago under $100. A good price for a nonstop flight from Walt Disney World to Chicago is less than $136.

  • Are there last-minute flights available from Walt Disney World to Chicago for under $100?

    There are currently 11+ open flights from Walt Disney World to Chicago within the next 7 days for less than $100.

  • What days are nonstop flights available from Walt Disney World to Chicago?

    Nonstop flights can be found on the following days: Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday.

  • How many flights depart from Walt Disney World to Chicago on average per day?

    On average, you can expect to see 19 flights from Walt Disney World to Chicago a day.
    Morning (6am - Noon) - 42% of flight departures
    Afternoon (Noon - 6pm) - 32% of flight departures
    Evening (6pm - Midnight) - 26% of flight departures

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

    Departing from Walt Disney World to Chicago will take you 2h 47m. The distance from Walt Disney World to Chicago is about 1011 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 $31 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $47 and Allegiant Air from $76 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: Southwest (100%), Japan Airlines (93%), SWISS( 90%).

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

    Looking at all options, your cheapest flight can be booked for $79. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $98 on average our data indicates $891 when flying from Walt Disney World to Chicago.

  • What does MCO to ORD mean?

    Orlando Airport is MCO and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Walt Disney World to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Walt Disney World to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Walt Disney World to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Walt Disney World to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Walt Disney World to Chicago that allow pets onboard?

    Many airlines flying from Walt Disney World to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Walt Disney World to Chicago?

    Yes, you can often find last-minute deals on Walt Disney World to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Walt Disney World to Chicago flight deals updated?

    The Walt Disney World to Chicago flight deals you see on this page were last updated on 11/5.

  • 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.

See more FAQs

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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.
Orlando to O'Hare Intl flights
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Orlando Sanford Intl to Rockford flights
Sarasota to Midway flights
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Panama City to Midway flights
Orlando to Peoria flights
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Gainesville to Midway flights
Daytona Beach to St. Louis flights
Daytona Beach to Midway flights
Tampa to Moline flights
Melbourne to St. Louis flights
Pensacola to St. Louis flights
Tampa to Evansville flights
Tampa to Peoria flights
Jacksonville to Peoria flights
Orlando to Evansville flights

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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$149FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$59Average$151FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$100Average$196FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$150Average$338FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$151Average$309FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$155Average$299FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$389FlexibilityNo cancel feeOn-timeN/A
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