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

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

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Find the cheapest month to fly from Chicago (MDW) to Orlando (ORL)

September is typically the cheapest month to fly

From $88 - $290 per traveler.

Alternative airports near Orlando

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

Select flight to Orlando Intl. MCO. Cheapest option available. Average driving time to city center is 19 minutes. Flights from $227
MCO
Orlando Intl.
Cheapest
Average driving time to city center19 min
Flights from $227

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) cost?
Grab a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
The cheapest month to fly from MDW to ORL is , when demand is low. Off-peak season is generally when airlines offer better prices between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
To find the cheapest airline that'll fly you from MDW to ORL, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
Direct flights from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to ORL?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
Choose a flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) that leaves before 3 PM to reduce the likelihood of delays. Departures later than this are on average 22% more likely to be 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.
What airports do you fly into for Orlando from Midway Intl. Airport (MDW)?
Check out your flight options from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO). This is the only airport in Orlando you can touch down at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) last-minute?
Last-minute fares from MDW to ORL are typically more expensive. To secure the lowest rates, start looking for flights well ahead of time. That being said, if you can play around with your travel dates, it's possible to land a cheap ticket right before your trip.
Is it cheaper to book a MDW to ORL flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to ORL flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the stress out of travel planning. Just secure your flights and choose from our extensive range of stays, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
In most instances, you can modify or cancel your MDW to ORL flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you want further details, visit our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Orlando Executive
Distance
982 mi

Book with confidence

Chicago to Orlando Flights

The cheapest times to fly from Chicago to Orlando

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 Chicago to Orlando are during the month of . You can find some of the cheapest flights from Chicago to Orlando with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Orlando

Sunday is one of the best days to book for cheap flights from Chicago to Orlando: 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 Chicago to Orlando

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 Chicago to Orlando 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 Chicago to Orlando 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 Chicago to Orlando 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.

 

Chicago to Orlando Flights

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