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

Popular airlines from Destin-Fort Walton Beach Airport (DSI) to Chicago O'Hare Intl. Airport (ORD)

Frequently asked questions

How much does a flight from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight or cheap return flight from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD) 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 Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD)?
is the most affordable month to fly from DSI to ORD. Planning your trip for the off-season is often the key to finding better fares.
Which airlines fly direct from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD)?
You can't catch a nonstop flight from Destin, FL (DSI-Destin-Fort Walton Beach) to O'Hare Intl. Airport (ORD). However, you can easily travel to Chicago without any layovers by taking off from Pensacola Intl. Airport (PNS).
What is the cheapest airline that flies from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from DSI to ORD. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD)?
You'll need to book a flight with a layover when traveling from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from DSI to ORD?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary 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 Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD)?
To arrive at O'Hare Intl. Airport (ORD) on schedule, choose a flight that leaves from Destin-Fort Walton Beach Airport (DSI) before 3 PM. The chance 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.
Is it cheaper to buy a plane ticket from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from DSI to ORD right before your journey is usually more expensive. But if there's some wiggle room with your travel dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a DSI to ORD flight and hotel package?
Opting for a DSI to ORD flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Pick from our impressive range of hotels and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Destin-Fort Walton Beach Airport (DSI) to O'Hare Intl. Airport (ORD)?
In most instances, you can cancel or reschedule your DSI to ORD flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you need more details, visit our Customer Service portal.

Travel information

Origin airport
Destin-Fort Walton Beach
Destination airport
O'Hare Intl.
Distance
804 mi

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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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*Available to One Key members.