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Cheap flights from Disney World to Chicago Midway (ORL - MDW)

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

What is the cheapest day to fly round-trip from Disney World to Chicago Midway?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

To save on the cost of your flight from Disney World to Chicago Midway, book at least 37 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $177 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $177.

Cheap flights from Disney World to Chicago Midway in July, August 2020

The best prices found for ORL to MDW flights for July, August
1 Jul - 5 Jul
$287pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
27 Jun - 28 Jun
$301pp
MCO
Orlando
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
24 Jun - 28 Jun
$318pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando

Disney World to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Disney World found for this year
4 Sep - 7 Sep
$146pp
MCO
Orlando
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MCO
Orlando
4 Sep - 7 Sep
$155pp
MCO
Orlando
Allegiant Air
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Allegiant Air
 
1 STOP
MCO
Orlando
3 Dec - 6 Dec
$161pp
MCO
Orlando
Cape Air
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Cape Air
 
1 STOP
MCO
Orlando

Last minute flights from Disney World to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Disney World, departing today and this week
27 Jun - 28 Jun
$301pp
MCO
Orlando
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
24 Jun - 28 Jun
$318pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
24 Jun - 28 Jun
$330pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando

One-way flights to Chicago Midway from Disney World

The cheapest one-way flights from Disney World to Chicago Midway
8:25 am - 2:40 pm
Delta
1 Stop
7h 15m
MCO - MDW
Delta
$73
Delta
12:42 pm - 3:03 pm
Multiple Airlines
2 Stops
27h 21m
MCO - MDW
Multiple Airlines
$100
Kiwi.com
2:05 pm - 2:33 am
Multiple Airlines
2 Stops
37h 28m
MCO - MDW
Multiple Airlines
$106
Kiwi.com

Related info for your journey

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

Flight FAQs

From Disney World to Chicago Midway

Are flight prices decreasing from Orlando to Chicago Midway 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 Midway 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.

Can I find flights from Disney World to Chicago Midway for under $200 on Cheapflights?

Yes, there are multiple flights from Disney World to Chicago Midway for under $200. The cheapest flight booked recently is on Delta for just $146, but on average you can expect to pay $249.

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

There are no nonstop flights from Disney World to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Disney World to Chicago Midway for under $400?

There are currently 16+ open flights from Disney World to Chicago Midway within the next 7 days for less than $400.

How popular is this flight route?

Flights from Orlando to Chicago Midway have been viewed 301 times in the past calendar month.

What is the cheapest airline for this route?

The cheapest airline for this route is Southwest Airlines Co.. When flying this airline from Orlando to Chicago Midway on average you can expect to find 146 flights available for this route daily.

Does it rain more in Orlando or Chicago Midway?

In Orlando, there will be greater rainfall in Orlando compared to Chicago Midway over the next 23 days.

Is Orlando weather warmer or cooler than Chicago Midway?

Temperatures around the 93 °F's can be experienced in July. The weather in Chicago Midway is colder than in Orlando. Plan for potential changes in flight availability as peak weather approaches in this location.

Alternative routes for Disney World to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Disney World to Chicago Midway
Average temperature for July in Chicago Midway
84.2 °F
Avg rainfall for July in Chicago Midway
3.7 ″

Airports servicing Orlando

Sanford (SFB)

Airports servicing Chicago

Hourly flight availability from Disney World to Chicago Midway

Morning 6 AM to noon 56% of ORL to MDW departures
Afternoon Noon to 6 PM 33% of ORL to MDW departures
Evening 6 PM to midnight 10% of ORL to MDW departures
Early morning Midnight to 6 AM 1% of ORL to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Disney World to Chicago Midway
Sunday
13 daily flights
Monday
15 daily flights
Tuesday
14 daily flights
Wednesday
14 daily flights
Thursday
15 daily flights
Friday
14 daily flights
Saturday
12 daily flights