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

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

Alternative airports near Destin

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Northwest Florida Regional VPS. Cheapest option available. Average driving time to city center is 29 minutes. Flights from $429
VPS
Northwest Florida Regional
Cheapest
Average driving time to city center29 min
Flights from $429

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) cost?
Lock in a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
is the least expensive month to fly from ORD to DSI. Avoiding peak travel times is often the key to finding a great deal.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest ORD to DSI flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
Direct flights from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to DSI?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary 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 O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) route, travel before 3 PM. Later departures have a 22% higher chance of being 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.
What airports do you fly into for Destin from O'Hare Intl. Airport (ORD)?
Compare your flight options from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS). This is the only airport in Destin you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI) last-minute?
Last-minute bookings from ORD to DSI are typically more expensive. To lock in the best prices, start looking for flights as soon as possible. That said, if you're flexible with your travel dates, you may land a cheap fare right before your trip.
Is it cheaper to book an ORD to DSI flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to DSI flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one easy place takes the hassle out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Destin-Fort Walton Beach Airport (DSI)?
Generally, it's possible to cancel or reschedule your ORD to DSI flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

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

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.