$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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Walt Disney World to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 May 1, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $106 (Cheapflightsfares) |
One-way from | $58 (FlightHub) |
Popular in | March |
Cheapest in | September |
Average price | $145 |
Find flight deals from Walt Disney World to Chicago
Cheapest flights from Walt Disney World to ChicagoExplore 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 May 1, 2025.
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 May 1, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 4/29. 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.
This Southwest deal was found by Cheapflights users on 4/29. 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.
This Delta deal was found by Cheapflights users on 4/30. 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.
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/30. 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.
This Mytrip deal was found by Cheapflights users on 4/30. 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.
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 May 1, 2025.
Use the filters below to find and compare flights from Bay Lake to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Wed 6/4
10:17 pm-12:36 am
Nonstop3h 19m
Chicago O'Hare Intl
Thu 6/12
5:15 am-8:58 am
Nonstop2h 43m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Tue 5/27
10:17 pm-12:20 am
Nonstop3h 03m
Chicago O'Hare Intl
Thu 5/29
9:17 am-1:11 pm
Nonstop2h 54m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Fri 5/30
9:42 pm-8:50 am
1 stop12h 08m
Chicago O'Hare Intl
Mon 6/9
4:35 pm-8:20 pm
Nonstop2h 45m
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 6/26
6:22 pm-8:17 pm
Nonstop2h 55m
Chicago Midway
Mon 6/30
9:12 pm-12:53 am
Nonstop2h 41m
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 5/30
12:09 pm-1:52 pm
Nonstop2h 43m
Chicago Greater Rockford
Mon 6/9
8:08 pm-11:38 pm
Nonstop2h 30m
OrlandoChicago
MCO - RFD
MCORFD
Orlando
Wed 6/25
6:30 am-8:31 am
1 stop27h 01m
Chicago Greater Rockford
Sun 6/29
9:21 am-12:36 am
1 stop14h 15m
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 6/4
2:40 pm-7:30 pm
1 stop5h 50m
Chicago Midway
Sat 6/7
5:45 pm-9:30 pm
Nonstop2h 45m
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Sat 7/19
6:15 am-12:29 pm
1 stop7h 14m
Chicago Midway
Tue 7/22
9:25 am-4:46 pm
1 stop6h 21m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Wed 5/21
11:45 am-1:50 pm
Nonstop3h 05m
Chicago O'Hare Intl
Tue 5/27
6:38 pm-10:28 pm
Nonstop2h 50m
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Sat 8/2
11:00 am-2:34 pm
1 stop4h 34m
Chicago O'Hare Intl
Wed 8/13
7:10 am-12:58 pm
1 stop4h 48m
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.
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 25, 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 May 1, 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 May 1, 2025.
The most flights from W9D to CHI are scheduled on a Wednesday (59 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 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 May 1, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
Comfort
Boarding
Entertainment
Food
Crew
Overall
Reviews
James,Apr 2025
LAX - SFO
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.
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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 2,558,603 searches. Data last updated May 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$153 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$164 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$100 | Average$198 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$155 | Average$344 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$351 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$323 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$430 | FlexibilityNo cancel fee | On-timeN/A |