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

MCO — CHI
Nov 8 — Nov 151
Sun 11/8
Sun 11/15
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Walt Disney World to Chicago are usually found in February or November, booked 53 days in advance, depart on a Friday or Thursday and return on a Tuesday

Find flight deals from Walt Disney World to Chicago

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

February

Average price

$189
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
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Highest demand for flights based on searches. 22% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Insights

Everything you need to know about your flight from Bay Lake to Chicago

What is the cheapest time of day to fly from W9D to CHI?

One of the essential ways to save on airfare from Walt Disney World to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 30% on airfare.

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

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

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest,United Airlines, andAllegiant Air from Bay Lake to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,224 reviews

Comfort

8.0

Entertainment

7.4

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,224 reviews
Southwest
7.9
Good
4,224 reviews

Comfort

8.0

Entertainment

7.4

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,327 reviews
Southwest
7.9
Good
4,224 reviews

Comfort

8.0

Entertainment

7.4

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Allegiant Air
7.3
Good
678 reviews
Southwest
7.9
Good
4,224 reviews

Comfort

8.0

Entertainment

7.4

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.0
Good
12,148 reviews
Southwest
7.9
Good
4,224 reviews

Comfort

8.0

Entertainment

7.4

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,551 reviews
Southwest
7.9
Good
4,224 reviews

Comfort

8.0

Entertainment

7.4

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • 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 $43 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $48 and Southwest from $78 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 (86%), ITA Airways (83%), ANA( 79%).

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

    Looking at all options, your cheapest flight can be booked for $110. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $101 on average, our data indicates $885 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Top 7 airlines flying from Walt Disney World to Chicago

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$216FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$83Average$193FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$280FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$146Average$330FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$155Average$335FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$373FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$362FlexibilityNo cancel feeOn-time69%

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