$150 Cheap Flights from Fort Walton Beach (VPS) to Chicago (ORD)

View $150 flight on Fri, May 8, 2026Opens 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 $150 for one-way flights and $302 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun Country Airlines
Fri, Dec 19 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$302 Roundtrip, found 4 days ago
$302
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Fri, Dec 19 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $302 found 4 days ago
Sun Country Airlines
Fri, Dec 19 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$312 Roundtrip, found 10 hours ago
$312
Roundtrip
found 10 hours ago
Select Sun Country Airlines flight, departing Fri, Dec 19 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $312 found 10 hours ago
Sun Country Airlines
Fri, Dec 19 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$322 Roundtrip, found 10 hours ago
$322
Roundtrip
found 10 hours ago
Select Sun Country Airlines flight, departing Fri, Dec 19 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $322 found 10 hours ago
Southwest Airlines
Wed, Dec 17 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$326 Roundtrip, found 4 days ago
$326
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 17 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $326 found 4 days ago
American Airlines
Wed, Dec 17 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$344 Roundtrip, found 4 days ago
$344
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Dec 17 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $344 found 4 days ago
Delta
Wed, Feb 11 - Sat, Feb 21
VPS
Fort Walton Beach
ORD
Chicago
$351 Roundtrip, found 8 hours ago
$351
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Feb 11 from Fort Walton Beach to Chicago, returning Sat, Feb 21, priced at $351 found 8 hours ago
American Airlines
Wed, Dec 17 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$357 Roundtrip, found 4 days ago
$357
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Dec 17 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $357 found 4 days ago
Southwest Airlines
Fri, Apr 10 - Mon, Apr 13
VPS
Fort Walton Beach
ORD
Chicago
$359 Roundtrip, found 2 days ago
$359
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Fort Walton Beach to Chicago, returning Mon, Apr 13, priced at $359 found 2 days ago
Southwest Airlines
Tue, Jan 13 - Tue, Jan 20
VPS
Fort Walton Beach
ORD
Chicago
$360 Roundtrip, found 3 days ago
$360
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Jan 13 from Fort Walton Beach to Chicago, returning Tue, Jan 20, priced at $360 found 3 days ago
American Airlines
Wed, Dec 17 - Sun, Dec 21
VPS
Fort Walton Beach
ORD
Chicago
$363 Roundtrip, found 4 days ago
$363
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Dec 17 from Fort Walton Beach to Chicago, returning Sun, Dec 21, priced at $363 found 4 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.

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. Closest option available. Average driving time to city center is 16 minutes. Flights from $495
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $495

Frequently asked questions

How much does a flight from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $150 or cheap return flight from $302 from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD)?
December is the most affordable month to fly from VPS to ORD. Avoiding peak travel times is often the key to finding a great deal.
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 Northwest Florida Regional Airport (VPS) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from VPS to ORD. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
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.

Travel information

Origin airport
Northwest Florida Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines
Roundtrip price
$301
Distance
796 mi
Average flight time
2 hours 42 mins

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 December. 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 $150 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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