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

Popular airlines from Orlando Sanford Intl. Airport (SFB) to Chicago Midway Airport (MDW)

Flights from Orlando (SFB) to Chicago (MDW)
Origin airport
Orlando Sanford Intl.
Destination airport
Midway Intl.
Distance
970 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 2026. 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 Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight or cheap return flight from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW) 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 Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW)?
is the least expensive month to fly from SFB to MDW. Timing your trip outside of the busy season is often the key to landing a great deal.
Which airlines fly direct from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW)?
While Orlando, FL (SFB-Orlando Sanford Intl.) doesn't have any 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 layovers.
What is the cheapest airline that flies from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from SFB to MDW, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from SFB to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*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 Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later departures are 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.
Is it cheaper to buy a plane ticket from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from SFB to MDW shortly before your trip is typically more expensive. However, if there's some wiggle room with your departure times and dates, you could score a cheap last-minute fare.
Is it cheaper to book a SFB to MDW flight and hotel package?
You'll generally save money by securing a SFB to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've selected your ideal flights and accommodations, consider adding extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Orlando Sanford Intl. Airport (SFB) to Midway Intl. Airport (MDW)?
You can usually cancel or reschedule your SFB to MDW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.