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

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

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Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI) cost?
Grab a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
Planning your trip for can help you save, as it's the cheapest month for flights between MDW and DSI. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to DSI flight.
How many flights per day from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
There are no daily nonstop flights available from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way in no time.
What day of the week has the most flights from MDW to DSI?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the airline, season 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 Destin-Fort Walton Beach Airport (DSI)?
To arrive at Destin-Fort Walton Beach Airport (DSI) on time, book a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Destin from Midway Intl. Airport (MDW)?
Northwest Florida Regional Airport (VPS) is the only airport in Destin with direct flights from Midway Intl. Airport (MDW). Explore the available options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI) last-minute?
Last-minute fares from MDW to DSI are usually more expensive. For the cheapest rates, start searching for flights well in advance. That said, if you're flexible with your travel plans, you may score a cheap fare right before your journey.
Is it cheaper to book a MDW to DSI flight and hotel package?
Opting for a MDW to DSI flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our extensive range of accommodations and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Destin-Fort Walton Beach Airport (DSI)?
Typically, you can cancel or modify your MDW to DSI flight. However, there may be additional charges, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you want further information, go to our Customer Service portal.

Travel information

Travel information

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

Book with confidence

Book with confidence

Chicago to Destin Flights

The cheapest times to fly from Chicago to Destin

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

 

The best time to book a flight from Chicago to Destin

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

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 Destin 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 Destin 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 Destin 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 Destin Flights

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*Available to One Key members.