Cheap Flights from Orlando (ORL) to Chicago (MDW)

Popular airlines from Orlando Executive Airport (ORL) to Chicago Midway Airport (MDW)

Today's featured flight deals from Orlando Executive Airport (ORL) to Chicago Midway Airport (MDW)

Nonstop
Carry-on included
Lower price than typical

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $62
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $62
Flights from Orlando (ORL) to Chicago (MDW)
Origin airport
Orlando Executive
Destination airport
Midway Intl.
Distance
982 mi

Orlando to Chicago Flights

The cheapest times to fly from Orlando to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Orlando to Chicago are during the month of . You can find some of the cheapest flights from Orlando to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Orlando to Chicago

Sunday is one of the best days to book for cheap flights from Orlando to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Orlando to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Orlando to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Orlando to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Orlando to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight or cheap return flight from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW)?
Planning your trip for is a great way to save, as it's the cheapest month for flights between ORL and MDW. You'll usually find the lowest fares during the off-season.
Which airlines fly direct from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW)?
Although Orlando, FL (ORL-Orlando Executive) has no direct flights to Midway Intl. Airport (MDW), other airports have nonstop options. Traveling from Orlando Intl. Airport (MCO) will get you to Chicago without any detours.
What is the cheapest airline that flies from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from ORL to MDW, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW)?
There aren't any daily direct flights departing from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from ORL to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary depending on various factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from ORL to MDW right before your journey is usually more expensive. However, if you're flexible with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book an ORL to MDW flight and hotel package?
You'll typically save money by booking an ORL to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've selected your preferred flights and accommodations, consider other add-ons like activities, car rentals and tours.
Can I cancel or change the date of my flight from Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW)?
In most cases, you can reschedule or cancel your ORL to MDW flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you need more details, head to our Customer Service portal.

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*Available to One Key members.