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$50+ Cheap flights from Chicago (CHI) to Bay Lake, FL

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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Walt Disney World are usually found in May or April, booked 30 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap flight deals from Chicago to Walt Disney World

Keep the following information in mind while searching for Chicago to Walt Disney World flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$115
(Mytrip)

One-way from

$50
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$279
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
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From Chicago (CHI) to Walt Disney World
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One-way flight from Chicago (CHI) to Walt Disney World
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Highest demand for flights based on searches. 11% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chicago to Walt Disney World

Cheapest flights from Chicago to Walt Disney World
Explore the most affordable flight options available from Chicago to Walt Disney World. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 3/197:21 pmORD - MCO
1 stop10h 48mSpirit Airlines
Wed 3/266:12 amMCO - ORD
1 stop11h 15mSpirit Airlines
Deal found 2/20$115
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 3/119:25 amORD - MCO
Nonstop2h 55mFrontier
Sat 3/154:37 pmMCO - ORD
Nonstop3h 17mFrontier
Deal found 2/20$117
This FlightHub deal was found by Cheapflights users on 2/20. 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.
Tue 2/257:07 amORD - MCO
1 stop7h 52mMultiple Airlines
Fri 2/287:05 amMCO - ORD
Nonstop3h 22mMultiple Airlines
Deal found 2/20$118
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/14:40 pmMDW - MCO
Nonstop2h 50mFrontier
Fri 4/45:54 pmMCO - MDW
Nonstop3h 01mFrontier
Deal found 2/19$118
This Mytrip deal was found by Cheapflights users on 2/20. 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 5/232:42 pmRFD - SFB
Nonstop2h 30mAllegiant Air
Sat 5/316:20 amSFB - RFD
Nonstop2h 46mAllegiant Air
Deal found 2/20$126
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/311:24 pmORD - MCO
1 stop6h 55mJetBlue
Wed 4/97:18 amMCO - ORD
1 stop6h 09mJetBlue
Deal found 2/19$197
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Mon 6/27:00 pmMDW - SFB
1 stop14h 35mAllegiant Air
Thu 6/59:53 pmSFB - MDW
1 stop22h 53mAllegiant Air
Deal found 2/19$213
This Southwest deal was found by Cheapflights users on 2/20. 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 3/187:05 amMDW - MCO
1 stop4h 15mSouthwest
Tue 3/256:30 pmMCO - MDW
1 stop5h 15mSouthwest
Deal found 2/20$233
This Delta deal was found by Cheapflights users on 2/19. 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.
Sun 3/302:55 pmMDW - MCO
1 stop7h 25mDelta
Tue 4/85:30 amMCO - MDW
1 stop4h 37mDelta
Deal found 2/19$249
This Mytrip deal was found by Cheapflights users on 2/20. 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 3/55:55 amORD - SFB
3 stops38h 27mMultiple Airlines
Wed 3/126:11 pmSFB - ORD
2 stops14h 33mMultiple Airlines
Deal found 2/20$298

Find flights from Chicago to Walt Disney World within your budget

Customize your flight search to find flights from Chicago to Walt Disney World 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 February 20, 2025.

Fly from

Chicago

Fly to

Walt Disney World

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 3/19

7:21 pm-7:09 am

1 stop10h 48m

Orlando

Wed 3/26

6:12 am-4:27 pm

1 stop11h 15m

$115

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 2/25

7:07 am-3:59 pm

1 stop7h 52m

Orlando

Fri 2/28

7:05 am-9:27 am

Nonstop3h 22m

$118

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 4/1

4:40 pm-8:30 pm

Nonstop2h 50m

Orlando

Fri 4/4

5:54 pm-7:55 pm

Nonstop3h 01m

$118

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 2/26

7:18 pm-11:16 pm

Nonstop2h 58m

Orlando

Wed 3/5

7:05 am-9:27 am

Nonstop3h 22m

$121

ChicagoOrlando

RFD - SFB

RFDSFB

Chicago Greater Rockford

Mon 3/10

6:50 pm-10:26 pm

Nonstop2h 36m

Orlando Sanford Intl

Wed 3/12

6:35 am-8:23 am

Nonstop2h 48m

$132

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 3/31

1:24 pm-9:19 pm

1 stop6h 55m

Orlando

Wed 4/9

7:18 am-12:27 pm

1 stop6h 09m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 3/18

7:05 am-12:20 pm

1 stop4h 15m

Orlando

Tue 3/25

6:30 pm-10:45 pm

1 stop5h 15m

$233

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 6/12

8:50 am-9:10 pm

1 stop11h 20m

Orlando

Mon 6/16

8:24 am-2:03 pm

1 stop6h 39m

$238

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 3/30

2:55 pm-11:20 pm

1 stop7h 25m

Orlando

Tue 4/8

5:30 am-9:07 am

1 stop4h 37m

$249

ChicagoOrlando

ORD - SFB

ORDSFB

Chicago O'Hare Intl

Wed 3/5

5:55 am-9:22 pm

3 stops38h 27m

Orlando Sanford Intl

Wed 3/12

6:11 pm-7:44 am

2 stops14h 33m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 29 results
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Best time to book a flight from Chicago to Walt Disney World

Have a flexible travel schedule? Discover the best time to fly to Walt Disney World from Chicago 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 Chicago to Walt Disney World

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

How far ahead should I book a flight from Chicago to Walt Disney World?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Walt Disney World. Price data was last updated on February 14, 2025.

The price you pay for your flight from Chicago to Walt Disney World may vary depending on when you book. For the best chance of a lower fare, look to book 30 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 Chicago to Walt Disney World?

Currently, May is the cheapest month in which you can book a flight from Chicago to Walt Disney World (average of $206). Flying from Chicago to Walt Disney World in November is currently the most expensive (average of $289). 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 CHI to W9D?

Find hourly flight availability from Chicago to Walt Disney World. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Walt Disney World as you normally would.

What is the cheapest day to fly from Chicago to Walt Disney World?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Walt Disney World. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Chicago to Walt Disney World flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Walt Disney World

Explore weekly flight availability from Chicago to Walt Disney World. 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 February 20, 2025.

The most flights from CHI to W9D are scheduled on a Thursday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).

Rainfall in Walt Disney World by month

Plan your trip to Walt Disney World by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Walt Disney World ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Walt Disney World when rainfall is around 2.4 in.

Temperature in Walt Disney World by month

Plan your trip to Walt Disney World by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Walt Disney World, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

Reviews of airlines servicing Walt Disney World

Get insights into the airlines that provide service to Walt Disney World. 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 Walt Disney World. Reviews last updated February 20, 2025.
Read through reviews of airlines operating flights from Chicago to Walt Disney World, such as Southwest, Delta and JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Walt Disney World. 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 Chicago to Walt Disney World one-way?

    The cheapest airlines for a one-way flight from Chicago to Walt Disney World are Frontier ($50), Spirit Airlines ($51), and Allegiant Air ($52).

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

    The most popular flight routes from Chicago to Walt Disney World are Chicago O'Hare Intl - Orlando, Chicago Midway - Orlando and Chicago Greater Rockford - Orlando Sanford Intl.

  • What are the most reliable airlines from Chicago to Walt Disney World?

    Before booking your flight to Walt Disney World from Chicago, check out the most reliable airlines to get you to your destination on time: Azul (87%), Copa Airlines (84%), Air Canada( 83%).

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

    While on average a flight from Chicago to Walt Disney World is generally $628, our data shows the cheapest flight currently is $46. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $60 for that flight.

  • Can I find deals for flights from Chicago to Walt Disney World that include hotel bookings?

    Yes. In addition to deals on Chicago to Walt Disney World flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Walt Disney World?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Walt Disney World.

  • Can I find deals for business class flights from Chicago to Walt Disney World?

    Yes. Cheapflights offers flight deals from Chicago to Walt Disney World 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 Chicago to Walt Disney World?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Walt Disney World (average of $206). Flying from Chicago to Walt Disney World in November is currently the most expensive (average of $289). 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 Chicago to Walt Disney World

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Walt Disney World

Discover the top 7 airlines that operate flights from Chicago to Walt Disney World. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$189FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$164FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$106Average$219FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$128Average$335FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$355FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$178Average$402FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$376FlexibilityNo cancel feeOn-timeN/A
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