Cheap flights from Disney World to Chicago (ORL - CHI)

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The best prices from Disney World to Chicago are usually found in August or July, booked 16 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

How to find the cheapest flight from
Disney World (ORL) to Chicago (CHI)

All the information you need to plan the best ORL to CHI flight in 2021: compare Disney World to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
ORL - CHI
Price
$56 - $184
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

December

High demand for flights, 30% potential price rise

Cheapest in

August

Best time to find cheap flights, 57% potential price drop

Average price

$124

Average for round-trip flights in May 2021

Round-trip from

$56

From Disney World to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Disney World to Chicago?

Flights from Disney World to Chicago are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Disney World to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 20 days in advance, which can save you up to 10% on flights from Disney World to Chicago compared to booking the week you need them. Waiting 20 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $137. For sooner than that we have options available in the next 3 days from $157.

What is the cheapest month to fly from Disney World to Chicago?

Our data shows that April tends to be the cheapest month to fly to Chicago from Disney World. Users have commonly found prices around $135 for the month, but tickets can be as low as $33. Due to multiple factors, prepare for potentially higher prices in December.

When is the cheapest time to fly from Disney World to Chicago (ORL - CHI)?

One of the essential ways to save on airfare from 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 afternoon could potentially save you up to 26% on airfare.

Cheap flights from Disney World to Chicago in May, June 2021

The best prices found for ORL to CHI flights for May, June
19 May - 26 May
$79pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
19 May - 25 May
$80pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MCO
Orlando
19 May - 19 May
$82pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando

Disney World to Chicago 2021 flight deals

Cheap flights to Chicago from Disney World found for this year
19 May - 26 May
$79pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
19 May - 25 May
$80pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MCO
Orlando
19 May - 19 May
$82pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando

Non-stop flights to Chicago from Disney World

Save time with Disney World to Chicago direct flight deals
22 May - 25 May
$79pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
25 May - 25 May
$85pp
MCO
Orlando
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MCO
Orlando
24 May - 25 May
$91pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MCO
Orlando

Last minute flights from Disney World to Chicago

Late deals on round-trip flights to Chicago from Disney World, departing today and this week
22 May - 25 May
$79pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
25 May - 25 May
$85pp
MCO
Orlando
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MCO
Orlando
24 May - 25 May
$91pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MCO
Orlando

One-way flights to Chicago from Disney World

The cheapest one-way flights from Disney World to Chicago
2:00 pm - 4:15 pm
American Airlines
Nonstop
3h 15m
MCO - ORD
American Airlines
1:38 pm - 3:14 pm
Allegiant Air
Nonstop
2h 36m
SFB - RFD
Allegiant Air
$65
mytrip.com
12:45 pm - 2:43 pm
United Airlines
Nonstop
2h 58m
MCO - ORD
United Airlines
$68
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Disney World</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Disney World to Chicago

Are flight prices decreasing from Orlando to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Orlando and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Which airlines flying from Orlando to Chicago have flexible cancellations due to COVID-19?

United Airlines, Spirit Airlines, and American Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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

Yes, there are multiple flights from Disney World to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $79, but on average you can expect to pay $99.

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

Cheapflights has at least 20 direct flights from Disney World to Chicago under $100. A good price for a nonstop flight from Disney World to Chicago is less than $98.

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

There are currently 20+ open flights from Disney World to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from Orlando to Chicago?

You can find nonstop flights on the following days: Monday, Wednesday, Saturday.

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

On average 7 flights depart from Orlando to Chicago per day.
Morning (6am - Noon) - 71% of flight departures
Afternoon (Noon - 6pm) - 29% of flight departures

Is Orlando weather warmer or cooler than Chicago?

Our data indicates that the weather will be 93 °F on average in the month of July. The temperature in Chicago is typically colder than in Orlando. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

How long is the flight from Disney World to Chicago?

Airlines like Allegiant Air fly from Disney World to Chicago in about 2h 34m. The time it takes to get you to your destination is usually consistent. Disney World and Chicago are separated by a distance of 996 mi. Generally, flights for this route are nonstop.

What are the cheapest airlines flying from Disney World to Chicago round-trip?

Cheapflights users have booked flights from Disney World to Chicago round-trip from $79. Other airlines that can offer you cheap pricing are United Airlines, from $85, and Allegiant Air, from $92. Spirit Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Disney World to Chicago one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $39. Allegiant Air flights start at $46 while deals on American Airlines start at $49 one-way.

Alternative routes for Disney World to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Disney World to Chicago.
Flight duration
2h 47m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing Orlando

Sanford (SFB)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Disney World to Chicago

The chart below displays the airlines Cheapflights users traveling from Disney World to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$38 $139 No cancel fee 62%
Spirit Airlines
$56 $180 No cancel fee 65%
American Airlines
$62 $209 No cancel fee 71%
Allegiant Air
$124 $227 No cancel fee 88%
United Airlines
$62 $238 No cancel fee 69%
Delta
$87 $261 No cancel fee N/A

Hourly flight availability from Disney World to Chicago

See what time of day planes typically take off from Disney World towards Chicago.
Afternoon Noon to 6 PM 46% of ORL to CHI departures
Morning 6 AM to noon 44% of ORL to CHI departures
Evening 6 PM to midnight 8% of ORL to CHI departures
Early morning Midnight to 6 AM 2% of ORL to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Disney World to Chicago
See how many times per day planes take to the skies headed from Disney World to Chicago.
Sunday
59 daily flights
Monday
48 daily flights
Tuesday
31 daily flights
Wednesday
36 daily flights
Thursday
47 daily flights
Friday
56 daily flights
Saturday
46 daily flights
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