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$48+ 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
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
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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 August 1, 2025.

Round-trip from

$235
(Southwest)

One-way from

$48
(Booking.com)

Popular in

March

Cheapest in

May

Average price

$217
From Fort Walton Beach to Chicago (CHI)
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One-way flight from Fort Walton Beach to Chicago (CHI)
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High demand for flights, 7% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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.
Fri 8/16:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Fri 8/89:12 amMDW - VPS
Nonstop2h 11mAllegiant Air
Deal found 7/30$145
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/247:00 amVPS - ORD
1 stop5h 45mSouthwest
Sat 9/272:55 pmORD - VPS
1 stop3h 50mSouthwest
Deal found 7/31$235
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:00 pmVPS - ORD
2 stops25h 18mMultiple Airlines
Sat 9/1311:57 amORD - VPS
2 stops24h 51mMultiple Airlines
Deal found 7/30$247
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/248:10 amVPS - ORD
1 stop6h 37mAmerican Airlines
Sat 9/278:45 amORD - VPS
Nonstop2h 28mAmerican Airlines
Deal found 7/31$249
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:00 pmVPS - MDW
1 stop6h 50mSouthwest
Sat 9/132:50 pmMDW - VPS
1 stop3h 55mSouthwest
Deal found 7/30$258
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/511:40 amVPS - ORD
1 stop4h 48mDelta
Sun 9/77:05 amORD - VPS
1 stop5h 54mDelta
Deal found 7/30$425
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/52:58 pmVPS - MDW
1 stop6h 28mDelta
Sun 9/76:00 amMDW - VPS
1 stop6h 59mDelta
Deal found 7/30$425

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 August 1, 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 - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 9/24

7:00 am-12:45 pm

1 stop5h 45m

Chicago O'Hare Intl

Sat 9/27

2:55 pm-6:45 pm

1 stop3h 50m

$235

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 9/11

3:00 pm-4:18 pm

2 stops25h 18m

Chicago O'Hare Intl

Sat 9/13

11:57 am-12:48 pm

2 stops24h 51m

$247

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 9/24

8:10 am-2:47 pm

1 stop6h 37m

Chicago O'Hare Intl

Sat 9/27

8:45 am-11:13 am

Nonstop2h 28m

$249

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 9/11

2:00 pm-8:50 pm

1 stop6h 50m

Chicago Midway

Sat 9/13

2:50 pm-6:45 pm

1 stop3h 55m

$258

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Fri 9/5

11:40 am-4:28 pm

1 stop4h 48m

Chicago O'Hare Intl

Sun 9/7

7:05 am-12:59 pm

1 stop5h 54m

$425

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 9/5

2:58 pm-9:26 pm

1 stop6h 28m

Chicago Midway

Sun 9/7

6:00 am-12:59 pm

1 stop6h 59m

$425

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 10/30

9:00 am-11:17 am

Nonstop2h 17m

$48

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Tue 9/2

11:00 am-1:36 pm

Nonstop2h 36m

$107

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 9/11

3:00 pm-4:18 pm

2 stops25h 18m

$111

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Sat 8/30

2:58 pm-7:19 pm

1 stop4h 21m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 results
1
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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 August 1, 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 August 1, 2025.

The most flights from FO9 to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

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 August 1, 2025.
Read through reviews of airlines operating flights from Fort Walton Beach to Chicago, such as Southwest, Delta, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
702 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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.
Sun Country Air
6.9
Okay
334 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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.

  • What are the cheapest airlines to fly from Fort Walton Beach to Chicago one-way?

    The cheapest airlines for a one-way flight from Fort Walton Beach to Chicago are Allegiant Air ($48), American Airlines ($107), and Delta ($112).

  • 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: Envoy Air (83%), Emirates (75%), United Airlines (75%).

  • 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 $4,881, our data indicates the cheapest price to be $138. The most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), is priced around $235.

  • 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
Valparaiso
Chesterton

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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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$201FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$157Average$339FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$362FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$323FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$223Average$393FlexibilityNo cancel feeOn-time69%

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