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$53+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$87
(Mytrip)

One-way from

$53
(Booking.com)

Popular in

September

Cheapest in

February

Average price

$191
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Chicago (CHI) flights.
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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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Highest demand for flights based on searches. 13% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Mytrip deal was found by Cheapflights users on 4/23. 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.
Mon 6/26:00 amVPS - MDW
Nonstop2h 22mAllegiant Air
Mon 6/169:12 amMDW - VPS
Nonstop2h 11mAllegiant Air
Deal found 4/23$87
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/411:08 amVPS - ORD
Nonstop2h 29mAmerican Airlines
Wed 6/117:43 amORD - VPS
Nonstop2h 16mAmerican Airlines
Deal found 4/23$158
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 6/49:18 amVPS - ORD
1 stop5h 29mDelta
Wed 6/117:10 amORD - VPS
1 stop5h 41mDelta
Deal found 4/22$177
This Southwest deal was found by Cheapflights users on 4/22. 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 6/47:55 amVPS - ORD
1 stop4h 50mSouthwest
Wed 6/117:30 amORD - VPS
2 stops10h 05mSouthwest
Deal found 4/22$300
This Sun Country Air deal was found by Cheapflights users on 4/22. 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.
Thu 7/36:02 pmVPS - ORD
1 stop18h 49mSun Country Air
Sun 7/66:45 amORD - VPS
1 stop10h 17mSun Country Air
Deal found 4/22$304
This Mytrip deal was found by Cheapflights users on 4/23. 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 6/126:02 pmVPS - ORD
1 stop23h 13mMultiple Airlines
Sun 6/159:35 pmORD - VPS
1 stop22h 44mMultiple Airlines
Deal found 4/23$310
This Southwest deal was found by Cheapflights users on 4/22. 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.
Tue 5/66:25 pmVPS - MDW
1 stop4h 45mSouthwest
Wed 5/76:20 amMDW - VPS
1 stop5h 05mSouthwest
Deal found 4/22$347
This Delta deal was found by Cheapflights users on 4/23. 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 6/61:25 pmVPS - MDW
1 stop4h 11mDelta
Mon 6/96:47 pmMDW - VPS
1 stop4h 40mDelta
Deal found 4/23$382

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 April 24, 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

Mon 6/2

6:00 am-8:22 am

Nonstop2h 22m

Chicago Midway

Mon 6/16

9:12 am-11:23 am

Nonstop2h 11m

$87

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 6/4

11:08 am-1:37 pm

Nonstop2h 29m

Chicago O'Hare Intl

Wed 6/11

7:43 am-9:59 am

Nonstop2h 16m

$158

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 6/4

9:18 am-2:47 pm

1 stop5h 29m

Chicago O'Hare Intl

Wed 6/11

7:10 am-12:51 pm

1 stop5h 41m

$177

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 6/4

7:55 am-12:45 pm

1 stop4h 50m

Chicago O'Hare Intl

Wed 6/11

7:30 am-5:35 pm

2 stops10h 05m

$300

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 7/3

6:02 pm-12:51 pm

1 stop18h 49m

Chicago O'Hare Intl

Sun 7/6

6:45 am-5:02 pm

1 stop10h 17m

$304

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Thu 6/12

6:02 pm-5:15 pm

1 stop23h 13m

Chicago O'Hare Intl

Sun 6/15

9:35 pm-8:19 pm

1 stop22h 44m

$310

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Tue 5/6

6:25 pm-11:10 pm

1 stop4h 45m

Chicago Midway

Wed 5/7

6:20 am-11:25 am

1 stop5h 05m

$347

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 6/6

1:25 pm-5:36 pm

1 stop4h 11m

Chicago Midway

Mon 6/9

6:47 pm-11:27 pm

1 stop4h 40m

$382

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 5/30

6:00 am-8:22 am

Nonstop2h 22m

$53

ValparaisoChicago

VPS - ORD

VPSORD

Valparaiso Destin-Ft Walton Beach

Wed 7/9

7:00 am-12:45 pm

1 stop5h 45m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 17 results
1
2

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 April 24, 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 May 5, 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. Tuesday mornings 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 April 24, 2025.

The most flights from FO9 to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
To help decide which airline to fly from Fort Walton Beach to Chicago, see what other customers have to say about Southwest, Delta and Avelo Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
7.3
Good
734 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
4,286 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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 ($53), Southwest ($88), and Sun Country Air ($137).

  • 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: American Airlines (100%), Qatar Airways (100%), Envoy Air (100%).

  • 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 $625, our data indicates the cheapest price to be $92. The most popular route (Valparaiso Destin-Ft Walton Beach - Chicago O'Hare Intl), is priced around $177.

  • 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 Fort Walton Beach?

Book flights to Fort Walton Beach if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$188FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$192Average$381FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$354FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$214Average$346FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$234Average$403FlexibilityNo cancel feeOn-time69%

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