HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$49+ Cheap flights from Fort Walton Beach, FL to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Fort Walton Beach to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Fort Walton Beach to Chicago

Keep the following information in mind while searching for Fort Walton Beach to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$155
(Cheapflightsfares)

One-way from

$49
(Cheapflightsfares)

Popular in

November

Cheapest in

May

Average price

$272
From Fort Walton Beach to Chicago (CHI)
Search Deals
One-way flight from Fort Walton Beach to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Fort Walton Beach to Chicago

Cheapest flights from Fort Walton Beach to Chicago
Explore the most affordable flight options available from Fort Walton Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:00 amVPS - MDW
Nonstop2h 17mAllegiant Air
Sun 10/2611:07 amMDW - VPS
Nonstop2h 05mAllegiant Air
Deal found 9/15$155
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Mon 12/19:24 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$158
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$167
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2511:31 amVPS - MDW
Nonstop2h 19mAllegiant Air
Mon 12/19:24 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$191
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2511:31 amVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/13$198
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Mon 12/19:24 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$230
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/235:24 pmVPS - MDW
Nonstop2h 19mAllegiant Air
Sat 11/299:09 amMDW - VPS
Nonstop2h 13mAllegiant Air
Deal found 9/14$240
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:30 amVPS - MDW
1 stop16h 55mMultiple Airlines
Sun 10/2611:07 amMDW - VPS
Nonstop2h 05mMultiple Airlines
Deal found 9/15$241
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:46 pmVPS - MDW
2 stops18h 35mMultiple Airlines
Sun 10/1911:07 amMDW - VPS
Nonstop2h 05mMultiple Airlines
Deal found 9/14$273
This Sun Country Air deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:56 pmVPS - ORD
1 stop17h 43mSun Country Air
Thu 11/279:20 amORD - VPS
1 stop23h 48mSun Country Air
Deal found 9/14$278
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:35 amVPS - MDW
2 stops16h 08mMultiple Airlines
Mon 12/19:24 amMDW - VPS
Nonstop2h 13mMultiple Airlines
Deal found 9/14$284
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:30 amVPS - ORD
1 stop10h 35mMultiple Airlines
Mon 10/207:43 pmORD - VPS
2 stops17h 05mMultiple Airlines
Deal found 9/13$307

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Walton Beach to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Fort Walton Beach to Chicago that are best for you.

Fly from

Fort Walton Beach

Fly to

Chicago

Route

Depart

Return

Price

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/23

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Sun 10/26

11:07 am-1:12 pm

Nonstop2h 05m

$155

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 11/20

5:24 pm-7:43 pm

Nonstop2h 19m

Chicago Midway

Mon 12/1

9:24 am-11:37 am

Nonstop2h 13m

$158

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 11/25

11:31 am-1:50 pm

Nonstop2h 19m

Chicago Midway

Mon 12/1

9:24 am-11:37 am

Nonstop2h 13m

$191

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 11/25

11:31 am-1:50 pm

Nonstop2h 19m

Chicago Midway

Sat 11/29

9:09 am-11:22 am

Nonstop2h 13m

$198

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/23

8:00 am-10:17 am

Nonstop2h 17m

Chicago Midway

Sun 10/26

11:57 am-1:32 pm

2 stops25h 35m

$244

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Sat 10/18

6:30 am-10:47 pm

2 stops16h 17m

Chicago Midway

Mon 10/20

12:08 pm-5:02 pm

1 stop4h 54m

$298

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 11/26

6:27 pm-8:20 am

1 stop13h 53m

Chicago O'Hare Intl

Sat 11/29

8:22 pm-9:08 am

1 stop12h 46m

$311

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 11/20

10:35 am-6:32 pm

1 stop7h 57m

Chicago O'Hare Intl

Thu 11/27

9:20 am-9:08 am

1 stop23h 48m

$311

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 10/11

6:30 am-5:05 pm

1 stop10h 35m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-12:50 pm

2 stops17h 07m

$312

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 10/17

3:46 pm-10:14 am

2 stops18h 28m

Chicago O'Hare Intl

Mon 10/20

11:13 am-12:48 pm

1 stop25h 35m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 results
1
2
3
4

Best time to book a flight from Fort Walton Beach to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Fort Walton Beach with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Fort Walton Beach to Chicago

What is the cheapest month to book a flight from Fort Walton Beach to Chicago?

Currently, August is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago (average of $245). Flying from Fort Walton Beach to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from FO9 to CHI?

Find hourly flight availability from Fort Walton Beach to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Fort Walton Beach to Chicago as you normally would.

What is the cheapest day to fly from Fort Walton Beach to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Fort Walton Beach to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Fort Walton Beach to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Fort Walton Beach to Chicago

Explore weekly flight availability from Fort Walton Beach to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from FO9 to CHI are scheduled on a Sunday (5 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Fort Walton Beach to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Fort Walton Beach to Chicago, such as Southwest, American Airlines, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Allegiant Air
7.2
Good
699 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Fort Walton Beach to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Fort Walton Beach to Chicago?

    Departing from Fort Walton Beach to Chicago will take you 2h 17m. There are 783 mi between Fort Walton Beach and Chicago. This flight may include one or multiple stops.

  • What are the most reliable airlines from Fort Walton Beach to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Fort Walton Beach to Chicago on time: Emirates (82%), United Airlines (82%), Air New Zealand (82%).

  • What are the cheapest flights from Fort Walton Beach to Chicago?

    Looking for the cheapest flight from Fort Walton Beach to Chicago? While on average our users pay $296, our data indicates the cheapest price to be $125. The most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), is priced around $307.

  • Can I find deals for flights from Fort Walton Beach to Chicago that include hotel bookings?

    Yes. In addition to deals on Fort Walton Beach to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Fort Walton Beach to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Fort Walton Beach to Chicago.

  • Can I find deals for business class flights from Fort Walton Beach to Chicago?

    Yes. Cheapflights offers flight deals from Fort Walton Beach to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Fort Walton Beach to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago (average of $245). Flying from Fort Walton Beach to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Fort Walton Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Orlando to Midway flights
Tampa to Midway flights
West Palm Beach to O'Hare Intl flights
Miami to Midway flights
Fort Myers to O'Hare Intl flights
Jacksonville to Midway flights
Orlando to St. Louis flights
Fort Lauderdale to Midway flights
Pensacola to O'Hare Intl flights
West Palm Beach to Midway flights
Fort Myers to Midway flights
Miami to St. Louis flights
Sarasota to O'Hare Intl flights
Tampa to St. Louis flights
Pensacola to Midway flights
Fort Lauderdale to St. Louis flights
Fort Myers to St. Louis flights
Daytona Beach to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Jacksonville to St. Louis flights
Panama City to O'Hare Intl flights
Gainesville to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Panama City to Midway flights
West Palm Beach to St. Louis flights
Sarasota to Midway flights
Valparaiso to O'Hare Intl flights
Orlando to Moline flights
Sarasota to St. Louis flights
Pensacola to St. Louis flights
Gainesville to Midway flights
Tallahassee to Midway flights
Key West to O'Hare Intl flights
Jacksonville to Peoria flights
Panama City to St. Louis flights
West Palm Beach to Moline flights
Orlando to Peoria flights
Valparaiso to Midway flights
Daytona Beach to St. Louis flights
Orlando to Rockford flights
Melbourne to St. Louis flights
Tampa to Moline flights
Jacksonville to Moline flights
Orlando Sanford Intl to Rockford flights
Key West to Midway flights

Top 5 airlines flying from Fort Walton Beach to Chicago

Discover the top 5 airlines that operate flights from Fort Walton Beach to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$157Average$348FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$324FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$310FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$211Average$378FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.