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72 € Cheap Flights from Chicago to Destin-Ft Walton Beach

Compare Chicago to Destin-Ft Walton Beach flight deals

Find the cheapest month or even day of the year to fly to Destin-Ft Walton Beach

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Flight deals from Chicago to Destin-Ft Walton Beach

Looking for a cheap last-minute deal or the best return flight from Chicago to Destin-Ft Walton Beach Airport? If you want to travel next month, return fares start from 126 €. Find the lowest prices on one-way and return tickets right here.
Destin.72 € per passenger.Departing Mon, 26 Oct, returning Thu, 19 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 26 Oct, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 19 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 72 €, select.
Destin.76 € per passenger.Departing Fri, 13 Nov, returning Thu, 19 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Fri, 13 Nov, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 19 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 76 €, select.
Destin.85 € per passenger.Departing Mon, 26 Oct, returning Fri, 30 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 26 Oct, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 30 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 85 €, select.
Destin.110 € per passenger.Departing Mon, 20 Jul, returning Fri, 31 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 20 Jul, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Fri, 31 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 110 €, select.
Destin.120 € per passenger.Departing Mon, 20 Jul, returning Mon, 3 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 20 Jul, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Mon, 3 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 120 €, select.
Destin.126 € per passenger.Departing Fri, 14 Aug, returning Mon, 17 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Fri, 14 Aug, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Mon, 17 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 126 €, select.
Destin.132 € per passenger.Departing Mon, 30 Nov, returning Sun, 20 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 30 Nov, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Sun, 20 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 132 €, select.
Destin.167 € per passenger.Departing Thu, 24 Dec, returning Thu, 31 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Thu, 24 Dec, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Thu, 31 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 167 €, select.
Destin.236 € per passenger.Departing Mon, 31 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 31 Aug, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Southwest Airlines, departs from Destin-Ft Walton Beach on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 236 €, select.
Destin.281 € per passenger.Departing Thu, 10 Sep, returning Sun, 13 Sep.Return flight with Frontier Airlines and Allegiant Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 10 Sep, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Allegiant Air, departs from Destin-Ft Walton Beach on Sun, 13 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 281 €, select.
Destin.345 € per passenger.Departing Wed, 17 Feb, returning Wed, 24 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 17 Feb, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Delta, departs from Destin-Ft Walton Beach on Wed, 24 Feb, arriving in Chicago Midway.Price includes taxes and charges.From 345 €, select.
Destin.394 € per passenger.Departing Mon, 28 Dec, returning Fri, 1 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 28 Dec, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Delta, departs from Destin-Ft Walton Beach on Fri, 1 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 394 €, select.
Destin.396 € per passenger.Departing Fri, 23 Apr, returning Thu, 29 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 23 Apr, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Delta, departs from Destin-Ft Walton Beach on Thu, 29 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From 396 €, select.
Destin.425 € per passenger.Departing Wed, 10 Mar, returning Sun, 14 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Mar, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Delta, departs from Destin-Ft Walton Beach on Sun, 14 Mar, arriving in Chicago Midway.Price includes taxes and charges.From 425 €, select.
Destin.482 € per passenger.Departing Sat, 1 Aug, returning Fri, 12 Mar.Return flight with Frontier Airlines and jetBlue.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 1 Aug, arriving in Destin-Ft Walton Beach.Inbound indirect flight with jetBlue, departs from Destin-Ft Walton Beach on Fri, 12 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 482 €, select.
Destin.518 € per passenger.Departing Wed, 30 Sep, returning Sun, 4 Oct.Return flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Wed, 30 Sep, arriving in Destin-Ft Walton Beach.Inbound indirect flight with Allegiant Air, departs from Destin-Ft Walton Beach on Sun, 4 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From 518 €, select.

Find the cheapest month to fly from Chicago to Destin-Ft Walton Beach

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Destin-Ft Walton Beach flights are currently cheapest in November.
Jul
from 110 €
Aug
from 126 €
Sep
from 281 €
Oct
from 85 €
Nov
from 76 €
Dec
from 167 €
Jan
Find prices
Feb
from 345 €
Mar
from 425 €
Apr
from 396 €
May
Find prices
Jun
Find prices

Direct flights from Chicago to Destin-Ft Walton Beach

Chicago to Destin-Ft Walton Beach: Alternative routes

Compare routes from Chicago to Destin below. You may find an airport to fly into that's cheaper, faster, or easier than Destin-Ft Walton Beach.

Destin Executive

3km from central Destin
Closest
Search flights

Destin-Ft Walton Beach

11km from central Destin
Cheapest
from 72 €
Search flights

Pensacola

67km from central Destin
from 184 €
Search flights

Northwest Florida Beaches International

68km from central Destin
from 191 €
Search flights

Chicago to Destin: Flight information

The things to know before you go.
Cheapest flight found72 €
Cheapest month to flyOctober
Average flight time2 hrs, 21 mins
Most popular airlineAmerican Airlines
Average flights per week18

Finding cheap flights from Chicago to Destin-Ft Walton Beach: Frequently asked questions

The best price we found for a return flight from Chicago to Destin-Ft Walton Beach is 72 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 21 minutes is the average flight time from Chicago to Destin-Ft Walton Beach.
American Airlines, Envoy Air and Allegiant Air fly direct from Chicago to Destin-Ft Walton Beach.
As of July 2026, there are 18 flights per week flying from Chicago to Destin-Ft Walton Beach.
The cheapest month to fly from Chicago to Destin-Ft Walton Beach is usually October.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Destin-Ft Walton Beach Airport on Monday, 26 October 2026.
Yes – the average flight time is 2 hours and 21 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Destin-Ft Walton Beach but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Destin is around 40 days in advance, so don’t leave your flight to the last minute.

The cheapest airline that flies to Destin-Ft Walton Beach is Allegiant Air .

Flying from Chicago to Destin-Fort Walton Beach Airport (VPS): What you need to know

  • Your travel plans take shape at one of Chicago's main airports, Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore your options for booking a flight from Chicago to Destin-Fort Walton Beach Airport (VPS) setting off from either of these bases.

  • The average duration of a direct Chicago to Destin-Fort Walton Beach Airport flight is 2 hours 25 minutes.

  • Destin's timezone is UTC-6, which is the same as Chicago. Destin-Fort Walton Beach Airport is located in Destin.

  • Chicago O'Hare International Airport (ORD) to Destin-Fort Walton Beach Airport (VPS) is the most popular route, with 6 direct services each week. Travel from ORD to VPS on American Airlines's 7:15am departure.

  • Your flight from Chicago to VPS won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • Going away during a peak month like July? High seasons (like Thanksgiving, Christmas and New Year) can add another hour at check-in and security. Play things extra safe and arrive up to four hours before international flights and two hours before domestic departures.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • You can hop on a direct flight from Chicago to Destin-Fort Walton Beach Airport (VPS) leaving from Chicago O'Hare International Airport (ORD).

  • When leaving from ORD, you can catch a direct flight from Chicago to Destin-Fort Walton Beach Airport with American Airlines.

  • The preferred choice for passengers flying between ORD and VPS is American Airlines.

  • Among carriers on this route, American Airlines has the highest percentage of on-time landings.

  • ORD is around 27 kilometres from central Chicago. If you're catching a taxi, driving or ride-sharing from the centre, it'll take 30 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the journey time to be around 45 minutes.

  • In search of a convenient hotel near Chicago O'Hare International Airport? If you've booked an early flight from Chicago to Destin-Fort Walton Beach Airport, these accommodation options will have you sleeping moments from check-in:

  • Of the flights that depart from Chicago O'Hare International Airport, 70% arrive as scheduled at their destination.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Consider starting your journey from Chicago Midway International Airport (MDW). You can book a direct Chicago to Destin-Fort Walton Beach Airport (VPS) plane ticket from this hub.

  • Board your direct flight from Chicago to VPS with Allegiant Air. This is one of the top carriers that operates this route out of MDW.

  • Allegiant Air is the top choice for bookings on the MDW to VPS route.

  • With 70.97% of services arriving as planned, Allegiant Air is the most punctual carrier flying between Chicago Midway International Airport and Destin-Fort Walton Beach Airport.

  • Using public transport, you can travel from central Chicago to MDW in about 30 minutes. The terminal is roughly 16 kilometres away, and getting there by car will take approximately 25 minutes.

  • Want to enjoy an extra night away before your Chicago to VPS flight? Unwind in a hotel near Chicago Midway International Airport before your holiday officially starts. Here's where you can stay:

  • 76% of flights out of Chicago Midway International Airport arrive within the expected time frame.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 145 kilometres from central Chicago. The drive from the city centre to the terminal takes about 1 hour 40 minutes. If you're planning to take public transport, expect a journey of around 2 hours.

  • Relax in bed for a little longer and still make your Chicago to Destin-Fort Walton Beach Airport flight with plenty of time to spare. These hotels near Chicago Rockford International Airport make departure day effortless if you're flying out first thing:

  • Airports have an on-time performance rating that measures how often flights land when they should. At RFD, that figure is 71%.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Destin-Fort Walton Beach Airport (VPS)

  • Hop off your flight from Chicago to Destin-Fort Walton Beach Airport and jump into your hotel bed soon after. If you're searching for a comfortable option a short drive from VPS, unpack your bags at TownePlace Suites Fort Walton Beach-Eglin AFB.

  • Lock in the best possible rate by booking your ride around two weeks ahead of your Chicago to Destin-Fort Walton Beach Airport flight.

How to find the cheapest flights from Chicago to Destin-Fort Walton Beach Airport (VPS)

  • Currently, 35 € is the lowest price we've found for a one-way ticket from Chicago to Destin-Fort Walton Beach Airport. The cheapest price for a return flight is 72 €. Keep in mind fares may change due to availability at the time of booking.

  • Booking in advance is often the key to finding a cheap flight from Chicago to VPS. Fares tend to rise as demand increases, so the closer you get to departure, the more expensive your ticket may be.

  • If you're flexible with your travel dates, try using the 'Whole month' tool. It'll show you the cheapest price across each month when searching for your Chicago to Destin-Fort Walton Beach Airport ticket.

  • Locking in a cheap plane ticket from Chicago to VPS is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know when the price has dropped.

  • Chase down a great fare on a flight from Chicago to Destin-Fort Walton Beach Airport with the help of the filters. Choose your preferred departure and arrival times, airlines and number of stops. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest.'

The best time to fly from Chicago to Destin-Fort Walton Beach Airport (VPS)

  • July is the most popular month for flights from Chicago to Destin-Fort Walton Beach Airport (VPS). Plan your visit to Destin in November if you'd rather be there when it's quieter.

  • The warmest month in Destin is August, with temperatures ranging between 25ºC (77ºF) and 33ºC (91ºF). Book your Chicago to VPS plane ticket then if that's your definition of good weather.

  • January sees temperatures of between 4ºC (39ºF) and 18ºC (64ºF). Search for cheap tickets from Chicago to Destin-Fort Walton Beach Airport around that time if you'd rather travel in cooler conditions.

More about Destin

  • Start your Destin trip right by choosing the ideal place to stay. Once you've booked your flight from Chicago to Destin-Fort Walton Beach Airport, check out our range of hotels including:

  • There are so many things to do and see in this city, it can be difficult to know where to start. Destin beach, Crystal Sands Beach and Public beach are top attractions which should be on any well-planned Destin itinerary.

Explore more of the United States

  • Destin is always a good idea, but there are so many other parts of the United States just waiting to be explored. About 209 kilometres north of Destin, a visit to Montgomery will keep you busy. Start with popular sights like Civil Rights Memorial, Dexter Avenue King Memorial Baptist Church and Rosa Parks Arrest Site.

  • Around 257 kilometres northeast of Destin, Columbus is another favourite stop in the United States. Start your sightseeing at The National Infantry Museum, Columbus Collective Museums and Columbus Museum.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.