$117 Cheap Flights from Fort Walton Beach (VPS) to Chicago (ORD)

View $117 flight on Tue, Oct 14, 2025Opens in a new window

Popular airlines from Northwest Florida Regional Airport (VPS) to Chicago O'Hare Intl. Airport (ORD)

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

Prices were available within the past 7 days and start at $117 for one-way flights and $225 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 22 - Wed, Nov 5
VPS
Fort Walton Beach
ORD
Chicago
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Fort Walton Beach to Chicago, returning Wed, Nov 5, priced at $225 found 4 days ago
Southwest Airlines
Tue, Aug 26 - Wed, Aug 27
VPS
Fort Walton Beach
ORD
Chicago
$235 Roundtrip, found 12 hours ago
$235
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Fort Walton Beach to Chicago, returning Wed, Aug 27, priced at $235 found 12 hours ago
American Airlines
Wed, Oct 22 - Wed, Nov 5
VPS
Fort Walton Beach
ORD
Chicago
$241 Roundtrip, found 4 days ago
$241
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Oct 22 from Fort Walton Beach to Chicago, returning Wed, Nov 5, priced at $241 found 4 days ago
American Airlines
Thu, Aug 21 - Fri, Aug 22
VPS
Fort Walton Beach
ORD
Chicago
$250 Roundtrip, found 5 days ago
$250
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Aug 21 from Fort Walton Beach to Chicago, returning Fri, Aug 22, priced at $250 found 5 days ago
American Airlines
Sun, Sep 21 - Tue, Sep 30
VPS
Fort Walton Beach
ORD
Chicago
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Sep 21 from Fort Walton Beach to Chicago, returning Tue, Sep 30, priced at $255 found 6 days ago
Southwest Airlines
Thu, Oct 30 - Sat, Nov 1
VPS
Fort Walton Beach
ORD
Chicago
$258 Roundtrip, found 1 hour ago
$258
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Fort Walton Beach to Chicago, returning Sat, Nov 1, priced at $258 found 1 hour ago
Southwest Airlines
Sat, Sep 13 - Tue, Sep 16
VPS
Fort Walton Beach
ORD
Chicago
$260 Roundtrip, found 21 hours ago
$260
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Sat, Sep 13 from Fort Walton Beach to Chicago, returning Tue, Sep 16, priced at $260 found 21 hours ago
Southwest Airlines
Wed, Oct 22 - Wed, Nov 5
VPS
Fort Walton Beach
ORD
Chicago
$260 Roundtrip, found 4 days ago
$260
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Fort Walton Beach to Chicago, returning Wed, Nov 5, priced at $260 found 4 days ago
Sun Country Airlines
Thu, Nov 6 - Wed, Nov 26
VPS
Fort Walton Beach
ORD
Chicago
$270 Roundtrip, found 16 hours ago
$270
Roundtrip
found 16 hours ago
Select Sun Country Airlines flight, departing Thu, Nov 6 from Fort Walton Beach to Chicago, returning Wed, Nov 26, priced at $270 found 16 hours ago
Delta
Sat, Sep 20 - Tue, Sep 23
VPS
Fort Walton Beach
ORD
Chicago
$316 Roundtrip, found 3 days ago
$316
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 20 from Fort Walton Beach to Chicago, returning Tue, Sep 23, priced at $316 found 3 days ago

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

June is typically the cheapest month to fly

From $157 - $532 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $361
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $361
Flights from Fort Walton Beach (VPS) to Chicago (ORD)
Origin airport
Northwest Florida Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines
Roundtrip price
$225
Distance
796 mi
Average flight time
2 hours 40 mins

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 October. 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 $117 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.

 

Frequently asked questions

How much does a flight from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD) cost?
Find affordable return tickets from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD) starting from $366. Reserve your seat and get ready to go. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving VPS on August 15 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from VPS to ORD?
The cheapest flights from VPS to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD)?
You can't catch a nonstop flight from Fort Walton Beach, FL (VPS-Northwest Florida Regional) to O'Hare Intl. Airport (ORD). However, you can easily travel to Chicago without any layovers by leaving from Pensacola Intl. Airport (PNS).
What is the cheapest airline that flies from VPS to ORD?
Journey from VPS to ORD with American Airlines. This carrier currently offers the cheapest one-way fare for this route, starting at $196. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from VPS on August 30 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD)?
There aren't any daily nonstop flights from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from VPS to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change 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 Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on schedule, select a flight that leaves Northwest Florida Regional Airport (VPS) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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're flying on a direct flight from Northwest Florida Regional Airport (VPS) to Chicago, Midway Intl. Airport (MDW) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book a flight from VPS to ORD generally means paying more. While it's possible to find some last-minute discounts, they aren't always guaranteed. Be flexible with your travel plans for a better chance of snagging a bargain.
Is it cheaper to book a VPS to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a VPS to ORD flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one easy place will take the hassle out of planning your trip. Just secure your flights and select from our wide range of hotels, then tailor your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD)?
If you reserved your VPS to ORD flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

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*Available to One Key members.