Cheap Flights from Kissimmee (ISM) to Chicago (MDW)

Popular airlines from Kissimmee, FL (ISM-Kissimmee Gateway) to Chicago Midway Airport (MDW)

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Frequently asked questions

How much does a flight from Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight or cheap return flight from Kissimmee Gateway Airport (ISM) 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 Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW)?
is the cheapest month to fly from ISM to MDW. Planning your trip for the off-season is often the key to finding a great deal.
Which airlines fly direct from Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW)?
While Kissimmee, FL (ISM-Kissimmee Gateway) 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 Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from ISM to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover if you're traveling from Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from ISM to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW) route, fly 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 Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from ISM to MDW right before your getaway is usually more expensive. But if you're flexible with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book an ISM to MDW flight and hotel package?
You'll typically save money by booking an ISM 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 easy to manage everything in one convenient place. After choosing your preferred flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Kissimmee Gateway Airport (ISM) to Midway Intl. Airport (MDW)?
If you reserved your ISM to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Origin airport
Kissimmee Gateway
Destination airport
Midway Intl.
Distance
997 mi

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Kissimmee to Chicago Flights

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

 

The best time to book a flight from Kissimmee to Chicago

Sunday is one of the best days to book for cheap flights from Kissimmee 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 Kissimmee 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 Kissimmee 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 Kissimmee 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 Kissimmee 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.

 

Kissimmee to Chicago Flights

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*Available to One Key members.