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

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

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Flights from Destin (DSI) to Chicago (ORD)
Origin airport
Destin-Fort Walton Beach
Destination airport
O'Hare Intl.
Distance
804 mi

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.

Frequently asked questions

Is it cheaper to buy a plane ticket from Destin-Fort Walton Beach Airport to ORD last minute?
When it comes to booking your flights, it’s always better to be prepared. While you may be able to find a deal on a Destin-Fort Walton Beach Airport (DSI) to ORD flight at the last minute, tickets usually don’t get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days in advance. For international journeys it’s three to four months.
What airports do you fly into for Chicago from Destin?
From Destin, you can get to Chicago via O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT). Check which hub is the most convenient for you before you make a decision. If you decide on O’Hare Intl. Airport (ORD), it’s roughly 16 mi northwest of the city center. Use the dollars you save when booking your fare with Expedia to experience the city’s top attractions, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from DSI to ORD?
We know life happens and plans change, so Expedia is here to help make amending your flight as easy as possible. To start, find your DSI to ORD itinerary through the Expedia Trips portal and read the fare conditions about what changes are allowed. If you booked your fare in the last 24 hours, some carriers allow you to cancel at no cost and organize new flights. If you bought your ticket more than 24 hours ago, connect with us via our Customer Service portal to find out your options.

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