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C$81 Cheap Flights from Chicago Midway to Destin-Ft Walton Beach

Compare Chicago Midway to Destin-Ft Walton Beach flight deals

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Flight deals from Chicago Midway to Destin-Ft Walton Beach

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway to Destin-Ft Walton Beach? Find the lowest prices on one-way and round-trip tickets right here.
Destin.C$81 per passenger.Departing Sun., Mar. 8.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun., Mar. 8, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$81, select.
Destin.C$81 per passenger.Departing Fri., Jun. 12.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Fri., Jun. 12, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$81, select.
Destin.C$82 per passenger.Departing Sun., May 3.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun., May 3, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$82, select.
Destin.C$91 per passenger.Departing Sun., Apr. 26.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun., Apr. 26, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$91, select.
Destin.C$114 per passenger.Departing Fri., Jul. 10.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Fri., Jul. 10, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$114, select.
Destin.C$131 per passenger.Departing Sun., Feb. 22.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun., Feb. 22, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$131, select.
Destin.C$145 per passenger.Departing Mon., Sep. 7.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon., Sep. 7, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From C$145, select.

Find the cheapest month to fly from Chicago Midway 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 Midway to Destin-Ft Walton Beach flights are currently cheapest in March.
Feb.
from C$131
Mar.
from C$81
Apr.
from C$91
May
from C$82
Jun.
from C$81
Jul.
from C$114
Aug.
Find prices
Sep.
from C$145
Oct.
Find prices
Nov.
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Dec.
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Jan.
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Direct flights from Chicago Midway to Destin-Ft Walton Beach

Chicago Midway to Destin-Ft Walton Beach: Alternative routes

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

Destin Executive

1km from central Destin
Closest
Search flights

Destin-Ft Walton Beach

11km from central Destin
Cheapest
from C$81
Search flights

Pensacola

67km from central Destin
from C$109
Search flights

Northwest Florida Beaches International

67km from central Destin
from C$139
Search flights

Chicago to Destin: Flight information

The things to know before you go.
Cheapest flight foundC$81
Cheapest month to flyMarch
Average flight time2 hrs, 11 mins
Most popular airlineAllegiant Air
Average flights per week2

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

The best price we found for a return flight from Chicago Midway to Destin-Ft Walton Beach is C$140. 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 11 minutes is the average flight time from Chicago Midway to Destin-Ft Walton Beach.
Allegiant Air flies direct from Chicago Midway to Destin-Ft Walton Beach.
As of February 2026, there are 2 flights per week flying from Chicago Midway to Destin-Ft Walton Beach.
The cheapest month to fly from Chicago Midway to Destin-Ft Walton Beach is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Destin-Ft Walton Beach Airport on Sunday, May 3, 2026.
Yes – the average flight time is 2 hours and 11 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.
Currently, Allegiant Air offers the cheapest flight tickets to Destin-Ft Walton Beach.

Traveling from Chicago Midway International Airport (MDW) to Destin Fort Walton Beach Airport (VPS): what you need to know

  • A direct flight from Chicago Midway International Airport to Destin Fort Walton Beach Airport takes on average 2 hours 17 minutes. Valparaiso's timezone is UTC-5 — the same as Chicago.

  • If you're jetting off during a public holiday or other peak period, allow for even more time. A good general rule is two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

  • If you want to have a stopover for your flight from Chicago Midway International Airport to Destin Fort Walton Beach Airport, just deselect 'Direct flights only' and explore your options. Here are the popular stopovers between MDW and VPS:

    • Hartsfield-Jackson Atlanta International Airport

    • Pittsburgh International Airport

    • Nashville International Airport

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

  • The lowest price we've found for a one-way ticket from Chicago Midway International Airport to Destin Fort Walton Beach Airport is C$81. For a return flight on this route, the best price is C$140. Depending on the availability and when you book, these fares can change.

  • To score cheap flight tickets from MDW to VPS, book your trip 9 months before your departure date.

  • Organize your trip for May. That's the cheapest month for flight tickets from Chicago Midway International Airport to Destin Fort Walton Beach Airport. If you're flexible with your travel dates, use the 'Whole month' tool to see the lowest price across every month.

  • Create a Price Alert for cheap flight tickets from MDW to VPS. There's no need to search every day to see if airfares have dropped. We'll tell you the moment there's a change in price.

  • Take advantage of filters to find the perfect journey for you. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Chicago Midway International Airport to Destin Fort Walton Beach Airport, use the 'Sort by' tool. You can also filter results by airline, arrival and departure times, and journey duration.

Handy information about Chicago Midway International Airport (MDW)

Arriving at Destin Fort Walton Beach Airport (VPS)

  • Consider staying at 310 Priscilla Dr Apartment after your flight from Chicago Midway International Airport to Destin Fort Walton Beach Airport. It's not too far from VPS and a good option if you'd like to freshen up right away.

Getting from Destin Fort Walton Beach Airport (VPS) to central Valparaiso

  • From Destin Fort Walton Beach Airport, Valparaiso is approximately 5 kilometres away. It takes around 6 minutes to reach the center driving.

When to fly to Destin Fort Walton Beach Airport (VPS)

  • July is the most popular month for flights from Chicago Midway International Airport to Destin Fort Walton Beach Airport. To skip the crowds, head to Valparaiso in April.

  • Before locking in your flight from Chicago Midway International Airport to Destin Fort Walton Beach Airport, think about the type of weather you like. August is the warmest month in Valparaiso, with the temperature ranging from 25ºC to 33ºC.

  • Search for cheap flight tickets from MDW to VPS in January if you like traveling in cooler conditions. Temperatures are at their lowest around then, ranging between 4ºC and 18ºC on average.

More about Valparaiso

Complete your Valparaiso trip with hotels and a car rental

  • You've booked your cheap ticket to Destin Fort Walton Beach Airport — next up is finding a great stay, and maybe even your own set of wheels. We've compared prices across hundreds of companies to bring you the best hotels and car rental deals in Valparaiso.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.