$141 Cheap Flights from Fort Walton Beach (VPS) to Chicago (MDW)

View $141 flight on Sat, Nov 1, 2025Opens in a new window

Popular airlines from Northwest Florida Regional Airport (VPS) to Chicago Midway Airport (MDW)

Cheap Flights from Fort Walton Beach to Chicago (VPS-MDW)

Prices were available within the past 7 days and start at $141 for one-way flights and $261 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Nov 1 - Tue, Nov 4
VPS
Fort Walton Beach
MDW
Chicago
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Fort Walton Beach to Chicago, returning Tue, Nov 4, priced at $261 found 6 days ago
Southwest Airlines
Thu, Oct 2 - Tue, Oct 7
VPS
Fort Walton Beach
MDW
Chicago
$312 Roundtrip, found 5 days ago
$312
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 2 from Fort Walton Beach to Chicago, returning Tue, Oct 7, priced at $312 found 5 days ago
Delta
Wed, Dec 24 - Thu, Jan 1
VPS
Fort Walton Beach
MDW
Chicago
$314 Roundtrip, found 1 hour ago
$314
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Dec 24 from Fort Walton Beach to Chicago, returning Thu, Jan 1, priced at $314 found 1 hour ago
Southwest Airlines
Wed, Dec 24 - Tue, Dec 30
VPS
Fort Walton Beach
MDW
Chicago
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Dec 24 from Fort Walton Beach to Chicago, returning Tue, Dec 30, priced at $315 found 2 days ago
Southwest Airlines
Thu, Oct 2 - Tue, Oct 7
VPS
Fort Walton Beach
MDW
Chicago
$317 Roundtrip, found 5 days ago
$317
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 2 from Fort Walton Beach to Chicago, returning Tue, Oct 7, priced at $317 found 5 days ago
Delta
Tue, Jan 6 - Wed, Jan 21
VPS
Fort Walton Beach
MDW
Chicago
$318 Roundtrip, found 6 days ago
$318
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jan 6 from Fort Walton Beach to Chicago, returning Wed, Jan 21, priced at $318 found 6 days ago
Southwest Airlines
Wed, Dec 24 - Tue, Dec 30
VPS
Fort Walton Beach
MDW
Chicago
$321 Roundtrip, found 2 days ago
$321
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Dec 24 from Fort Walton Beach to Chicago, returning Tue, Dec 30, priced at $321 found 2 days ago
Delta
Fri, Jan 16 - Tue, Jan 27
VPS
Fort Walton Beach
MDW
Chicago
$323 Roundtrip, found 6 days ago
$323
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jan 16 from Fort Walton Beach to Chicago, returning Tue, Jan 27, priced at $323 found 6 days ago
Southwest Airlines
Sat, Nov 1 - Tue, Nov 4
VPS
Fort Walton Beach
MDW
Chicago
$327 Roundtrip, found 6 days ago
$327
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Fort Walton Beach to Chicago, returning Tue, Nov 4, priced at $327 found 6 days ago
Southwest Airlines
Sat, Oct 11 - Wed, Oct 15
VPS
Fort Walton Beach
MDW
Chicago
$332 Roundtrip, found 4 hours ago
$332
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Oct 11 from Fort Walton Beach to Chicago, returning Wed, Oct 15, priced at $332 found 4 hours ago

Find the cheapest month to fly from Fort Walton Beach (VPS) to Chicago (MDW)

July is typically the cheapest month to fly

From $155 - $715 per traveler.

Frequently asked questions

How much does a flight from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $141 or cheap return flight from $261 from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
The cheapest month to fly from VPS to MDW is November, when there's less demand. Off-peak season is usually when better flight deals are available between these airports.
What is the cheapest airline that flies from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from VPS to MDW. Then, sort your results by "Price (lowest to highest)" to pick up a good deal.
How many flights per day from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
On average, there are 2 direct flights taking off from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW) every week. If you don't find one that fits your schedule, think about hopping on a flight with a layover. Customize your search results on Expedia to include one stop or more and choose the best alternative.
What are the most popular departure times for flights from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
The 1 PM departures from VPS to MDW are typically the busiest. Prices can be higher for these popular slots. If you're hoping to save money, choose a less crowded time to fly.
What day of the week has the most flights from VPS to MDW?
If you jet off on a Thursday, you'll get the largest range of choices for flights from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW).
What is the earliest flight from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
Hop on the earliest flight at around 1:18PM UTC-6, leaving from Northwest Florida Regional Airport (VPS). You'll be traveling for approximately 2h 23m, arriving at Midway Intl. Airport (MDW) at approximately 3:41PM UTC-6.
How long does it take to fly from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
Flights from VPS to MDW have an average travel time of 2 hours and 23 minutes. The distance between the two airports is 780 mi.
What is the best time to fly from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
Book a flight from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Later departures are on average 22% more likely to be 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 Chicago from Northwest Florida Regional Airport (VPS)?
If you've booked a direct flight from Northwest Florida Regional Airport (VPS) to Chicago, Midway Intl. Airport (MDW) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from VPS to MDW shortly before your journey is typically more expensive. But if there's some wiggle room with your schedule, you could grab a cheap last-minute fare.
Is it cheaper to book a VPS to MDW flight and hotel package?
You'll generally save money by securing a VPS to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've selected your preferred flights and accommodations, consider adding extras including tours, car rentals and activities.
Can I cancel or change the date of my flight from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
If you reserved your VPS to MDW flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Travel information

Origin airport
Northwest Florida Regional
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$261
Distance
782 mi

Book with confidence

Book with confidence

Fort Walton Beach to Chicago Flights

The cheapest times to fly from Fort Walton Beach 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 Fort Walton Beach to Chicago are during the month of November. You can find some of the cheapest flights from Fort Walton Beach to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Fort Walton Beach to Chicago

Sunday is one of the best days to book for cheap flights from Fort Walton Beach 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 Fort Walton Beach 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 Fort Walton Beach to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $141 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 Fort Walton Beach 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 Fort Walton Beach 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.

 

Fort Walton Beach to Chicago Flights

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*Available to One Key members.