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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)

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

Round-trip from

$56

From Disney World to Chicago

One-way from

$42

One-way flight 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 evening could potentially save you up to 29% on airfare.

Cheap flights from Disney World to Chicago in January, February 2021

The best prices found for ORL to CHI flights for January, February
28 Jan - 3 Feb
$34pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando
3 Feb - 7 Feb
$35pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
22 Jan - 24 Jan
$36pp
MCO
Orlando
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando

Disney World to Chicago 2021 flight deals

Cheap flights to Chicago from Disney World found for this year
28 Jan - 3 Feb
$34pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando
3 Feb - 7 Feb
$35pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
22 Jan - 24 Jan
$36pp
MCO
Orlando
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando

Non-stop flights to Chicago from Disney World

Save time with Disney World to Chicago direct flight deals
28 Jan - 3 Feb
$34pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando
3 Feb - 7 Feb
$35pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
12 Feb - 15 Feb
$36pp
MCO
Orlando
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
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
28 Jan - 3 Feb
$34pp
MCO
Orlando
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando
28 Jan - 1 Feb
$37pp
MCO
Orlando
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MCO
Orlando
29 Jan - 31 Jan
$39pp
MCO
Orlando
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
MCO
Orlando

One-way flights to Chicago from Disney World

The cheapest one-way flights from Disney World to Chicago
10:45 am - 12:56 pm
American Airlines
Nonstop
3h 11m
MCO - ORD
American Airlines
10:10 am - 11:56 am
Allegiant Air
Nonstop
2h 46m
SFB - RFD
Allegiant Air
$50
mytrip.com
4:55 pm - 3:51 am
Multiple Airlines
1 Stop
11h 56m
MCO - ORD
Multiple Airlines
$51
Kiwi.com

Related info for your journey

Useful info, stats and facts about Disney World to Chicago 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.

What safety measures are being taken by airlines flying from Orlando to Chicago to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Orlando to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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 Multiple Airlines for just $34, but on average you can expect to pay $44.

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 $44.

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.

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, Spirit Airlines, and Frontier fly from Disney World to Chicago in about 2h 41m. The time it takes to get you to your destination is usually consistent. 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 $36. Another airline that can offer you cheap pricing is Spirit Airlines. Frontier is 72% 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 Frontier, which is currently one of the cheapest options available, starting at $14. Spirit Airlines flights start at $19 while deals on American Airlines start at $42 one-way.

Alternative routes for Disney World to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Disney World to Chicago
Flight duration
2h 52m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

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

Afternoon Noon to 6 PM 62% of ORL to CHI departures
Morning 6 AM to noon 29% of ORL to CHI departures
Early morning Midnight to 6 AM 6% of ORL to CHI departures
Evening 6 PM to midnight 3% of ORL to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Disney World to Chicago
Sunday
42 daily flights
Monday
35 daily flights
Tuesday
29 daily flights
Wednesday
28 daily flights
Thursday
36 daily flights
Friday
41 daily flights
Saturday
31 daily flights
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