Cheap Flights from Destin (DSI) to Chicago (MDW)

Popular airlines from Destin-Fort Walton Beach Airport (DSI) to Chicago Midway Airport (MDW)

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Frequently asked questions

How much does a flight from Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Destin-Fort Walton Beach Airport (DSI) 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 Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW)?
is the most affordable month to fly from DSI to MDW. Traveling during an off-peak travel window is often the key to finding a great deal.
What is the cheapest airline that flies from Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from DSI to MDW. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW)?
There are no daily direct flights from Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from DSI to MDW?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary depending on a number of factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Departures after this time 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 Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from DSI to MDW right before your trip is generally 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 DSI to MDW flight and hotel package?
You'll typically save money by booking a DSI 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 simple to manage everything in one convenient place. Once you've selected your ideal flights and accommodations, consider adding extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Destin-Fort Walton Beach Airport (DSI) to Midway Intl. Airport (MDW)?
In most cases, you can cancel or reschedule your DSI to MDW flight. However, additional charges may apply, especially if you booked over 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you need further information, go to our Customer Service portal.

Travel information

Travel information

Origin airport
Destin-Fort Walton Beach
Destination airport
Midway Intl.
Distance
790 mi

Book with confidence

Book with confidence

Destin to Chicago Flights

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

 

The best time to book a flight from Destin to Chicago

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

 

Destin to Chicago Flights

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Explore a world of travel with Expedia

*Available to One Key members.