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Cheap flights from Orlando to Chicago Midway (ORL - MDW)

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

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

Saturday flights are generally found to be more expensive for flights from Orlando to Chicago Midway. 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 Midway.

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

Find a great deal and save up to 10% by booking at least 37 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Orlando to Chicago Midway within the next two weeks, with the cheapest ticket starting at $177.

When is the cheapest time to fly from Orlando to Chicago Midway (ORL - MDW)?

It’s typically best to fly out from Orlando to Chicago Midway in the evening. Doing so could potentially save you 42% on the flight price compared to flying in the noon, which is usually more expensive.

Cheap flights from Orlando to Chicago Midway in August, September 2020

The best prices found for ORL to MDW flights for August, September
8 Aug - 14 Aug
$210pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
23 Jul - 26 Jul
$234pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
23 Jul - 26 Jul
$242pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando

Orlando to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Orlando found for this year
14 Sep - 18 Sep
$158pp
MCO
Orlando
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MCO
Orlando
8 Aug - 14 Aug
$210pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
15 Oct - 17 Oct
$218pp
MCO
Orlando
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MCO
Orlando

Last minute flights from Orlando to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Orlando, departing today and this week
23 Jul - 26 Jul
$234pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
MCO
Orlando
23 Jul - 26 Jul
$242pp
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 Orlando

The cheapest one-way flights from Orlando to Chicago Midway
12:25 pm - 5:05 pm
Allegiant Air
1 Stop
5h 40m
MCO - MDW
Allegiant Air
$79
Ovago
2:00 pm - 5:25 pm
Delta
1 Stop
4h 25m
MCO - MDW
Delta
$99
Delta
5:40 am - 2:16 pm
Multiple Airlines
2 Stops
9h 36m
MCO - MDW
Multiple Airlines
$521
United

Related info for your journey

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

Flight FAQs

From Orlando 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 Orlando to Chicago Midway for under $200 on Cheapflights?

Yes, there are multiple flights from Orlando to Chicago Midway for under $200. The cheapest flight booked recently is on Delta for just $158, but on average you can expect to pay $411.

Are there nonstop flights from Orlando to Chicago Midway for under $200 on Cheapflights?

There are no nonstop flights from Orlando 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 Orlando to Chicago Midway for under $300?

There are currently 2+ open flights from Orlando to Chicago Midway within the next 7 days for less than $300.

What days are nonstop flights available from Orlando to Chicago Midway?

Days when nonstop flights are available for this flight are: Sunday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from Orlando to Chicago Midway on average per day?

On average 1 flight departs from Orlando to Chicago Midway per day.
Afternoon (Noon - 6pm) - 100% of flight departures

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 24 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.

How long is the flight from Orlando to Chicago Midway?

For as low as $751, Delta can have you in Chicago Midway from Orlando in 4h 29m. There are 996 mi between Orlando and Chicago Midway.

What is the cheapest airline to fly from Orlando to Chicago Midway round-trip?

Delta, at $158, was found to be the cheapest airline from Orlando to Chicago Midway.. Delta is priced at 33% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Orlando to Chicago Midway one-way?

The cheapest airlines for a one-way flight from Orlando to Chicago Midway are Allegiant Air ($79) and Delta ($99).

Alternative routes for Orlando to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Orlando to Chicago Midway
Average temperature for August in Chicago Midway
82.4 °F
Avg rainfall for August in Chicago Midway
3.9 ″

Airports servicing Orlando

Sanford (SFB)

Airports servicing Chicago

Hourly flight availability from Orlando to Chicago Midway

Morning 6 AM to noon 59% of ORL to MDW departures
Afternoon Noon to 6 PM 27% of ORL to MDW departures
Evening 6 PM to midnight 13% 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 Orlando to Chicago Midway
Sunday
11 daily flights
Monday
13 daily flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
0 flights
Friday
13 daily flights
Saturday
11 daily flights