$74+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Mar 5 — Mar 121
1 adult, Economy
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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
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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
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Cheapest flights from Fort Walton Beach to ChicagoExplore 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 February 3, 2026.
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 February 3, 2026.
This Mytrip deal was found by Cheapflights users on 2/2. 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 2/121:01 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Sun 2/223:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$99
This eDestinos deal was found by Cheapflights users on 2/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1512:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Thu 2/194:10 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/128:48 pm
VPS
- MDW
2 stops25h 37m
Multiple Airlines
Sun 2/223:40 pm
MDW
- VPS
Nonstop2h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/1512:31 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Thu 2/199:05 am
MDW
- VPS
2 stops29h 32m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$263
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Thu 3/58:46 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$279
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/251:00 pm
VPS
- ORD
Nonstop2h 44m
American Airlines
Wed 4/14:00 pm
ORD
- VPS
1 stop6h 24m
American Airlines
Deal found 2/3![American Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/57:40 am
VPS
- ORD
1 stop17h 00m
Multiple Airlines
Mon 3/94:44 pm
ORD
- VPS
2 stops44h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 2/1. 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 7/111:37 am
VPS
- ORD
Nonstop2h 42m
American Airlines
Thu 7/98:38 am
ORD
- VPS
Nonstop2h 29m
American Airlines
Deal found 2/1![American Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 2/1. 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 3/117:05 am
VPS
- ORD
2 stops11h 36m
Delta
Tue 3/249:50 am
ORD
- VPS
1 stop6h 18m
Delta
Deal found 2/1![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 2/3. 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 3/2512:35 pm
VPS
- ORD
2 stops9h 20m
Southwest
Wed 4/12:40 pm
ORD
- VPS
1 stop6h 35m
Southwest
Deal found 2/3![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 2/1. 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 3/117:05 am
VPS
- ORD
2 stops11h 36m
Delta
Wed 3/189:35 am
ORD
- VPS
2 stops13h 40m
Delta
Deal found 2/1![Delta logo]()
$344
This American Airlines deal was found by Cheapflights users on 1/31. 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.
Thu 4/2312:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Mon 4/279:41 am
ORD
- VPS
Nonstop2h 34m
American Airlines
Deal found 1/31![American Airlines logo]()
$354
Best flights from Fort Walton Beach to ChicagoDiscover carefully curated flight deals from Fort Walton Beach to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Fort Walton Beach to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This eDestinos deal was found by Cheapflights users on 2/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1512:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Thu 2/194:10 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/1512:31 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Thu 2/199:05 am
MDW
- VPS
2 stops29h 32m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 2/2. 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 7/111:37 am
VPS
- ORD
Nonstop2h 42m
American Airlines
Thu 7/98:38 am
ORD
- VPS
Nonstop2h 29m
American Airlines
Deal found 2/2![American Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 2/1. 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 3/257:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Wed 4/12:40 pm
ORD
- VPS
1 stop6h 35m
Southwest
Deal found 2/1![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 2/1. 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 3/117:05 am
VPS
- ORD
2 stops11h 36m
Delta
Tue 3/249:50 am
ORD
- VPS
1 stop6h 18m
Delta
Deal found 2/1![Delta logo]()
$340
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Thu 3/58:46 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/57:40 am
VPS
- ORD
1 stop17h 00m
Multiple Airlines
Mon 3/94:44 pm
ORD
- VPS
2 stops44h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 2/1. 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 3/117:05 am
VPS
- ORD
2 stops11h 36m
Delta
Wed 3/189:35 am
ORD
- VPS
2 stops13h 40m
Delta
Deal found 2/1![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 2/3. 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 4/2212:30 pm
VPS
- ORD
2 stops9h 25m
Southwest
Wed 4/2911:55 am
ORD
- VPS
2 stops9h 05m
Southwest
Deal found 2/3![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 4/234:46 pm
VPS
- ORD
1 stop7h 08m
American Airlines
Mon 4/279:41 am
ORD
- VPS
Nonstop2h 34m
American Airlines
Deal found 2/2![American Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 2/1. 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 7/17:45 am
VPS
- ORD
1 stop4h 24m
Delta
Thu 7/96:00 am
ORD
- VPS
1 stop7h 29m
Delta
Deal found 2/1![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 4/2412:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Mon 4/273:04 pm
ORD
- VPS
1 stop8h 46m
American Airlines
Deal found 2/3![American Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sat 2/1411:15 am
VPS
- MDW
1 stop5h 50m
Southwest
Thu 2/195:25 am
MDW
- VPS
1 stop5h 05m
Southwest
Deal found 2/1![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 2/1. 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.
Mon 3/167:24 pm
VPS
- ORD
1 stop4h 30m
Delta
Tue 3/247:10 am
ORD
- VPS
1 stop7h 00m
Delta
Deal found 2/1![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 2/1. 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 3/1712:35 pm
VPS
- MDW
2 stops8h 15m
Southwest
Sat 3/215:25 am
MDW
- VPS
2 stops10h 30m
Southwest
Deal found 2/1![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:15 am
VPS
- MDW
1 stop4h 52m
Delta
Mon 4/276:00 am
MDW
- VPS
1 stop6h 48m
Delta
Deal found 1/31![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 2/1. 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 4/174:59 pm
VPS
- MDW
1 stop5h 29m
Delta
Sun 4/196:00 am
MDW
- VPS
1 stop6h 48m
Delta
Deal found 2/1![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 2/1. 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 7/12:40 pm
VPS
- MDW
1 stop7h 05m
Delta
Thu 7/96:00 am
MDW
- VPS
1 stop6h 25m
Delta
Deal found 2/1![Delta logo]()
$376
Last-minute flights from Fort Walton Beach to ChicagoDiscover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated February 3, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 2/2. 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 2/121:01 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Sun 2/223:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/128:48 pm
VPS
- MDW
2 stops25h 37m
Multiple Airlines
Sun 2/223:40 pm
MDW
- VPS
Nonstop2h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$252
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sat 2/147:15 am
VPS
- ORD
1 stop5h 00m
Southwest
Wed 2/181:45 pm
ORD
- VPS
1 stop5h 10m
Southwest
Deal found 2/1![Southwest logo]()
$366
This eDestinos deal was found by Cheapflights users on 2/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1512:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Thu 2/194:10 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/1512:31 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Thu 2/199:05 am
MDW
- VPS
2 stops29h 32m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$263
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Thu 3/58:46 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/57:40 am
VPS
- ORD
1 stop17h 00m
Multiple Airlines
Mon 3/94:44 pm
ORD
- VPS
2 stops44h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 3/512:30 pm
VPS
- ORD
Nonstop2h 44m
American Airlines
Mon 3/99:40 am
ORD
- VPS
Nonstop2h 29m
American Airlines
Deal found 2/1![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 2/1. 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 3/117:05 am
VPS
- ORD
2 stops11h 36m
Delta
Tue 3/249:50 am
ORD
- VPS
1 stop6h 18m
Delta
Deal found 2/1![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 2/1. 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 3/117:05 am
VPS
- ORD
2 stops11h 36m
Delta
Wed 3/189:35 am
ORD
- VPS
2 stops13h 40m
Delta
Deal found 2/1![Delta logo]()
$344
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/251:00 pm
VPS
- ORD
Nonstop2h 44m
American Airlines
Wed 4/14:00 pm
ORD
- VPS
1 stop6h 24m
American Airlines
Deal found 2/3![American Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 2/3. 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 3/257:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Wed 4/12:40 pm
ORD
- VPS
1 stop6h 35m
Southwest
Deal found 2/3![Southwest logo]()
$335
One-way flights from Fort Walton Beach to ChicagoSearch for one-way flight options from Fort Walton Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Fort Walton Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/191:01 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 2/3![Allegiant Air logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 5/102:40 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/268:40 pm
VPS
- ORD
2 stops38h 11m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/57:40 am
VPS
- ORD
1 stop17h 00m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/307:30 am
VPS
- ORD
1 stop15h 13m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/198:48 pm
VPS
- MDW
2 stops25h 37m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/18:40 pm
VPS
- ORD
2 stops38h 11m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 6/143:12 pm
VPS
- MDW
1 stop28h 18m
Allegiant Air
Deal found 2/3![Allegiant Air logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/2710:00 am
VPS
- ORD
2 stops37h 17m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/2710:00 am
VPS
- MDW
2 stops29h 19m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$171
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 5/16:15 pm
VPS
- MDW
1 stop5h 15m
Southwest
Deal found 2/2![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 2/3. 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 2/192:30 pm
VPS
- MDW
1 stop5h 40m
Southwest
Deal found 2/3![Southwest logo]()
$215
Find 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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $149 (eDestinos) |
One-way from | $74 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $200 |
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 February 3, 2026.
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
Sun 2/15
12:31 pm-2:50 pm
Nonstop2h 19m
Chicago Midway
Thu 2/19
4:10 pm-6:16 pm
Nonstop2h 06m
$149
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sun 2/15
12:31 pm-2:50 pm
Nonstop2h 19m
Chicago Midway
Thu 2/19
9:05 am-2:37 pm
2 stops29h 32m
$268
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sun 3/1
12:31 pm-2:50 pm
Nonstop2h 19m
Chicago Midway
Thu 3/5
8:46 pm-10:54 pm
Nonstop2h 08m
$279
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 3/5
7:40 am-12:40 am
1 stop17h 00m
Chicago O'Hare Intl
Mon 3/9
4:44 pm-12:54 pm
2 stops44h 10m
$330
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/1
11:37 am-2:19 pm
Nonstop2h 42m
Chicago O'Hare Intl
Thu 7/9
8:38 am-11:07 am
Nonstop2h 29m
$335
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 3/25
7:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Wed 4/1
2:40 pm-9:15 pm
1 stop6h 35m
$335
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 3/11
7:05 am-6:41 pm
2 stops11h 36m
Chicago O'Hare Intl
Tue 3/24
9:50 am-4:08 pm
1 stop6h 18m
$340
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 3/11
7:05 am-6:41 pm
2 stops11h 36m
Chicago O'Hare Intl
Wed 3/18
9:35 am-11:15 pm
2 stops13h 40m
$344
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/1
7:45 am-12:09 pm
1 stop4h 24m
Chicago O'Hare Intl
Thu 7/9
6:00 am-1:29 pm
1 stop7h 29m
$354
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Mon 3/16
7:24 pm-11:54 pm
1 stop4h 30m
Chicago O'Hare Intl
Tue 3/24
7:10 am-2:10 pm
1 stop7h 00m
$354
Showing 1-10 of 39 results
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.
VPS-MDW
VPS-ORD
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
FO9-CHI
VPS-MDW
VPS-ORD
What is the cheapest month to book a flight from Fort Walton Beach to Chicago?
Currently, November is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago (average of $87). Flying from Fort Walton Beach to Chicago in September is currently the most expensive (average of $209). 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 February 3, 2026.
One of the essential ways to save on airfare from Fort Walton Beach to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 32% on airfare.
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 February 3, 2026.
The most flights from FO9 to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Wednesday, 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 February 3, 2026.
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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Other flights to Chicago
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Fort Walton Beach and Chicago flights
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Top 6 airlines flying from Fort Walton Beach to Chicago
Discover the top 6 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$144 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$269 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$155 | Average$201 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$157 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$173 | Average$349 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$209 | Average$326 | FlexibilityNo cancel fee | On-time69% |