$88 Cheap Flights from Fort Walton Beach (VPS) to Chicago (ORD)

View $88 flight on Tue, Jul 15, 2025Opens in a new window

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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $88 for one-way flights and $158 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Jul 22 - Tue, Jul 29
VPS
Fort Walton Beach
ORD
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 22 from Fort Walton Beach to Chicago, returning Tue, Jul 29, priced at $158 found 1 day ago
Southwest Airlines
Tue, Jul 22 - Tue, Jul 29
VPS
Fort Walton Beach
ORD
Chicago
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 22 from Fort Walton Beach to Chicago, returning Tue, Jul 29, priced at $177 found 1 day ago
Delta
Fri, Jun 6 - Mon, Jun 9
VPS
Fort Walton Beach
ORD
Chicago
$177 Roundtrip, found 5 hours ago
$177
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Jun 6 from Fort Walton Beach to Chicago, returning Mon, Jun 9, priced at $177 found 5 hours ago
Delta
Thu, May 22 - Mon, May 26
VPS
Fort Walton Beach
ORD
Chicago
$187 Roundtrip, found 6 hours ago
$187
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, May 22 from Fort Walton Beach to Chicago, returning Mon, May 26, priced at $187 found 6 hours ago
American Airlines
Fri, Jun 20 - Wed, Jun 25
VPS
Fort Walton Beach
ORD
Chicago
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Jun 20 from Fort Walton Beach to Chicago, returning Wed, Jun 25, priced at $197 found 7 hours ago
Southwest Airlines
Tue, Jul 22 - Tue, Jul 29
VPS
Fort Walton Beach
ORD
Chicago
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 22 from Fort Walton Beach to Chicago, returning Tue, Jul 29, priced at $217 found 1 day ago
American Airlines
Fri, Jul 4 - Wed, Jul 9
VPS
Fort Walton Beach
ORD
Chicago
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 4 from Fort Walton Beach to Chicago, returning Wed, Jul 9, priced at $222 found 1 day ago
Delta
Fri, May 30 - Mon, Jun 2
VPS
Fort Walton Beach
ORD
Chicago
$227 Roundtrip, found 7 hours ago
$227
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, May 30 from Fort Walton Beach to Chicago, returning Mon, Jun 2, priced at $227 found 7 hours ago
American Airlines
Fri, Jul 4 - Wed, Jul 9
VPS
Fort Walton Beach
ORD
Chicago
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 4 from Fort Walton Beach to Chicago, returning Wed, Jul 9, priced at $232 found 1 day ago
Sun Country Airlines
Fri, May 9 - Mon, May 26
VPS
Fort Walton Beach
ORD
Chicago
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Fri, May 9 from Fort Walton Beach to Chicago, returning Mon, May 26, priced at $346 found 1 day ago

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 $176. 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 May 21 2025 and touching down at ORD. The price was last updated on April 24 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 $142. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from VPS on July 5 2025. Prices were last updated on April 24 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.
*Available to One Key members.