Chicago

$56+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Nov 25 — Dec 21
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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 Saturday 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 20, 2024.

Popular in

June

Cheapest in

February

Round-trip from

$106
(Cheapflightsfares)

One-way from

$56
(Trip.com)
High demand for flights, 25% potential price rise
Best time to find cheap flights, 30% potential price drop
From Walt Disney World to Chicago (CHI)
One-way flight from Walt Disney World to Chicago (CHI)

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 20, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/55:34 pmMCO - ORD
1 stop7h 17mFrontier
Mon 12/94:58 pmORD - MCO
1 stop7h 45mFrontier
Deal found 11/19$106
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/64:46 pmMCO - ORD
Nonstop3h 04mSpirit Airlines
Sun 12/89:58 amORD - MCO
1 stop11h 13mSpirit Airlines
Deal found 11/19$107
This Gotogate deal was found by Cheapflights users on 11/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/66:35 amSFB - RFD
Nonstop2h 54mAllegiant Air
Wed 12/1812:49 pmRFD - SFB
Nonstop2h 41mAllegiant Air
Deal found 11/19$113
This Frontier deal was found by Cheapflights users on 11/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/168:26 amMCO - MDW
Nonstop2h 55mFrontier
Mon 12/1612:36 pmMDW - MCO
1 stop10h 22mFrontier
Deal found 11/19$113
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:11 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Mon 12/163:25 pmORD - MCO
1 stop7h 46mMultiple Airlines
Deal found 11/19$121
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/176:15 amMCO - MDW
1 stop4h 35mDelta
Tue 12/1712:44 pmMDW - MCO
1 stop6h 07mDelta
Deal found 11/19$212
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:12 amMCO - ORD
Nonstop3h 18mAmerican Airlines
Sat 12/147:13 pmORD - MCO
Nonstop2h 48mAmerican Airlines
Deal found 11/19$237
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:25 amMCO - MDW
Nonstop2h 55mSouthwest
Tue 12/107:15 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 11/19$281
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/110:10 pmMCO - RFD
2 stops18h 31mMultiple Airlines
Sun 12/84:11 pmRFD - MCO
2 stops30h 40mMultiple Airlines
Deal found 11/19$696
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/218:51 amSFB - RFD
2 stops24h 10mMultiple Airlines
Sun 11/241:48 pmRFD - SFB
2 stops20h 24mMultiple Airlines
Deal found 11/18$707

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 1/16

10:45 am-10:12 pm

1 stop12h 27m

Chicago O'Hare Intl

Mon 1/20

3:56 pm-1:46 am

1 stop8h 50m

$106

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 12/6

4:46 pm-6:50 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sun 12/8

9:58 am-10:11 pm

1 stop11h 13m

$107

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/9

12:40 pm-6:37 pm

1 stop6h 57m

Chicago Midway

Mon 1/13

4:28 pm-1:48 am

1 stop8h 20m

$108

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 12/6

6:35 am-8:29 am

Nonstop2h 54m

Chicago Greater Rockford

Wed 12/18

12:49 pm-4:30 pm

Nonstop2h 41m

$113

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 1/16

1:57 pm-4:08 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/26

10:59 am-2:51 pm

Nonstop2h 52m

$116

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 1/15

2:00 pm-6:49 pm

1 stop5h 49m

Chicago O'Hare Intl

Tue 1/28

11:05 am-4:09 pm

1 stop4h 04m

$196

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 12/17

6:15 am-9:50 am

1 stop4h 35m

Chicago Midway

Tue 12/17

12:44 pm-7:51 pm

1 stop6h 07m

$212

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 12/14

8:25 am-10:15 am

Nonstop2h 50m

Chicago Midway

Sun 12/15

8:00 pm-11:40 pm

Nonstop2h 40m

$258

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Sun 12/1

10:10 pm-3:41 pm

2 stops18h 31m

Chicago Greater Rockford

Sun 12/8

4:11 pm-11:51 pm

2 stops30h 40m

$696

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/18

10:52 pm-6:39 am

1 stop8h 47m

$56

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 November 15, 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 November 20, 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 18, 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 November 20, 2024.

The most flights from W9D to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 20, 2024.
Get a feel of what it's like to fly with Frontier, Delta and Spirit 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.
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.1
Very good
5,014 reviews
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.0
Very good
8,756 reviews
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.8
Good
288 reviews
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.4
Good
9,171 reviews
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.3
Good
2,811 reviews
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

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.
  • 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 $56 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $57 and Spirit Airlines from $57 one-way.

  • What are the most popular routes from Walt Disney World to Chicago?

  • 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%), ANA( 90%).

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

    Looking at all options, your cheapest flight can be booked for $57. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $93 on average our data indicates $930 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.

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.

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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$56Average$154FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$109Average$196FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$147Average$347FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$153Average$312FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$155Average$332FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$446FlexibilityNo cancel feeOn-timeN/A
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