$119+ Cheap flights from Chicago (CHI) to Fort Walton Beach, FL
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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Chicago to Fort Walton Beach 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.Cheapflights Tip: The best prices from Chicago to Fort Walton Beach are usually found in October or June, booked 17 days in advance, depart on a Monday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Fort Walton Beach
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Best
Last-minute
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Cheapest flights from Chicago to Fort Walton BeachExplore the most affordable flight options available from Chicago to Fort Walton Beach. 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 Chicago to Fort Walton Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
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.
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Fri 7/36:05 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$157
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 3/13:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Sun 3/85:40 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$159
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 2/263:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Sun 3/112:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$227
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 3/13:40 pm
MDW
- VPS
Nonstop2h 06m
Multiple Airlines
Sun 3/87:00 am
VPS
- MDW
2 stops12h 47m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$231
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 2/263:40 pm
MDW
- VPS
Nonstop2h 06m
Multiple Airlines
Sun 3/18:40 pm
VPS
- MDW
2 stops23h 07m
Multiple Airlines
Deal found 2/1![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.
Thu 3/127:30 am
MDW
- VPS
1 stop6h 20m
Multiple Airlines
Sun 3/155:37 pm
VPS
- MDW
Nonstop2h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$254
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.
Mon 6/89:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Sat 6/277:12 pm
VPS
- MDW
1 stop18h 44m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$274
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 4/184:20 pm
MDW
- VPS
1 stop4h 40m
Southwest
Sat 4/2512:10 pm
VPS
- MDW
1 stop6h 05m
Southwest
Deal found 2/1![Southwest logo]()
$278
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 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Mon 4/68:00 am
VPS
- MDW
2 stops38h 19m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$283
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 5/302:15 pm
MDW
- VPS
1 stop6h 45m
Southwest
Sat 6/611:40 am
VPS
- MDW
1 stop7h 55m
Southwest
Deal found 2/1![Southwest logo]()
$299
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:45 pm
ORD
- VPS
1 stop5h 10m
Southwest
Sat 3/77:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Deal found 1/31![Southwest logo]()
$307
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:15 am
MDW
- VPS
1 stop5h 05m
Southwest
Sat 3/74:40 pm
VPS
- MDW
1 stop7h 25m
Southwest
Deal found 1/31![Southwest logo]()
$307
Best flights from Chicago to Fort Walton BeachDiscover carefully curated flight deals from Chicago to Fort Walton Beach 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 Chicago to Fort Walton Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
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 2/263:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Sun 3/112:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$227
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 3/127:30 am
MDW
- VPS
1 stop6h 20m
Multiple Airlines
Sun 3/155:37 pm
VPS
- MDW
Nonstop2h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$254
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 4/184:20 pm
MDW
- VPS
1 stop4h 40m
Southwest
Sat 4/2512:10 pm
VPS
- MDW
1 stop6h 05m
Southwest
Deal found 2/1![Southwest logo]()
$278
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:47 pm
MDW
- VPS
1 stop5h 52m
Delta
Tue 4/76:00 am
VPS
- MDW
1 stop3h 56m
Delta
Deal found 2/2![Delta logo]()
$335
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.
Fri 3/69:05 am
ORD
- VPS
Nonstop2h 29m
American Airlines
Fri 3/134:40 pm
VPS
- ORD
1 stop7h 36m
American Airlines
Deal found 2/2![American Airlines logo]()
$364
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:15 am
MDW
- VPS
1 stop5h 05m
Southwest
Sat 3/74:40 pm
VPS
- MDW
1 stop7h 25m
Southwest
Deal found 1/31![Southwest logo]()
$307
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 5/21:55 pm
ORD
- VPS
1 stop7h 05m
Southwest
Wed 5/67:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Deal found 2/1![Southwest logo]()
$307
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.
Sat 5/164:30 pm
MDW
- VPS
1 stop6h 23m
Delta
Thu 5/216:00 am
VPS
- MDW
1 stop3h 51m
Delta
Deal found 2/1![Delta logo]()
$354
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.
Sat 4/255:59 pm
ORD
- VPS
1 stop5h 20m
Delta
Mon 4/271:53 pm
VPS
- ORD
1 stop6h 23m
Delta
Deal found 1/31![Delta logo]()
$354
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.
Tue 3/3111:00 am
MDW
- VPS
2 stops10h 15m
Southwest
Tue 4/77:15 am
VPS
- MDW
2 stops7h 40m
Southwest
Deal found 2/2![Southwest logo]()
$346
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.
Thu 5/285:30 am
MDW
- VPS
1 stop3h 50m
Southwest
Sat 6/611:40 am
VPS
- MDW
1 stop7h 55m
Southwest
Deal found 2/1![Southwest logo]()
$347
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 4/181:55 pm
ORD
- VPS
1 stop7h 05m
Southwest
Sat 4/257:00 am
VPS
- ORD
2 stops14h 55m
Southwest
Deal found 2/1![Southwest logo]()
$359
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.
Tue 3/316:00 am
ORD
- VPS
2 stops15h 15m
Southwest
Tue 4/77:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Deal found 2/2![Southwest logo]()
$365
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/102:40 pm
ORD
- VPS
1 stop6h 35m
Southwest
Fri 3/137:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Deal found 1/31![Southwest logo]()
$373
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.
Thu 3/262:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Tue 3/317:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Deal found 2/2![Southwest logo]()
$383
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.
Fri 4/176:00 am
ORD
- VPS
2 stops9h 20m
Southwest
Mon 4/207:20 am
VPS
- ORD
2 stops14h 35m
Southwest
Deal found 2/1![Southwest logo]()
$390
Last-minute flights from Chicago to Fort Walton BeachDiscover last-minute flight deals from Chicago to Fort Walton Beach. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Fort Walton Beach. Data last updated February 3, 2026 and is based on user searches.
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 2/263:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Sun 3/112:31 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$227
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 2/263:40 pm
MDW
- VPS
Nonstop2h 06m
Multiple Airlines
Sun 3/18:40 pm
VPS
- MDW
2 stops23h 07m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$252
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 3/13:40 pm
MDW
- VPS
Nonstop2h 06m
Allegiant Air
Sun 3/85:40 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$159
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 3/13:40 pm
MDW
- VPS
Nonstop2h 06m
Multiple Airlines
Sun 3/87:00 am
VPS
- MDW
2 stops12h 47m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$231
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:15 am
MDW
- VPS
1 stop5h 05m
Southwest
Sat 3/74:40 pm
VPS
- MDW
1 stop7h 25m
Southwest
Deal found 1/31![Southwest logo]()
$307
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:45 pm
ORD
- VPS
1 stop5h 10m
Southwest
Sat 3/77:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Deal found 1/31![Southwest logo]()
$307
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.
Tue 3/39:31 am
ORD
- VPS
Nonstop2h 29m
American Airlines
Sat 3/712:10 pm
VPS
- ORD
Nonstop2h 44m
American Airlines
Deal found 1/31![American Airlines logo]()
$316
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 3/127:30 am
MDW
- VPS
1 stop6h 20m
Multiple Airlines
Sun 3/155:37 pm
VPS
- MDW
Nonstop2h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$254
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.
Tue 3/179:40 am
ORD
- VPS
Nonstop2h 29m
American Airlines
Thu 3/267:42 am
VPS
- ORD
1 stop7h 39m
American Airlines
Deal found 2/2![American Airlines logo]()
$345
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.
Tue 3/244:00 pm
ORD
- VPS
1 stop6h 15m
American Airlines
Wed 4/17:42 am
VPS
- ORD
1 stop5h 52m
American Airlines
Deal found 2/2![American Airlines logo]()
$335
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:47 pm
MDW
- VPS
1 stop5h 52m
Delta
Tue 4/76:00 am
VPS
- MDW
1 stop3h 56m
Delta
Deal found 2/3![Delta logo]()
$335
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.
Tue 3/315:30 pm
MDW
- VPS
1 stop3h 45m
Southwest
Tue 4/710:25 am
VPS
- MDW
2 stops6h 25m
Southwest
Deal found 2/2![Southwest logo]()
$341
One-way flights from Chicago to Fort Walton BeachSearch for one-way flight options from Chicago to Fort Walton Beach. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Chicago to Fort Walton Beach. 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 2/2. 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.
Wed 3/46:51 pm
ORD
- VPS
1 stop19h 01m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$119
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.
Sat 2/286:51 pm
ORD
- VPS
1 stop19h 08m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$125
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.
Tue 3/38:16 pm
ORD
- VPS
2 stops41h 36m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$136
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.
Fri 2/276:51 pm
ORD
- VPS
2 stops40h 50m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$147
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 2/285:40 am
MDW
- VPS
1 stop4h 55m
Southwest
Deal found 2/1![Southwest logo]()
$166
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 5/83:50 pm
MDW
- VPS
1 stop5h 15m
Southwest
Deal found 2/2![Southwest logo]()
$188
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.
Fri 2/275:15 am
MDW
- VPS
1 stop8h 00m
Southwest
Deal found 2/1![Southwest logo]()
$217
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.
Fri 3/278:15 am
MDW
- VPS
1 stop9h 00m
Southwest
Deal found 2/1![Southwest logo]()
$263
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.
Fri 5/87:30 am
MDW
- VPS
3 stops35h 43m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$277
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.
Sat 2/2811:06 am
MDW
- VPS
1 stop4h 57m
Delta
Deal found 2/1![Delta logo]()
$454
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 2/2712:45 pm
MDW
- VPS
1 stop5h 34m
Delta
Deal found 2/1![Delta logo]()
$479
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.
Fri 3/206:07 pm
MDW
- VPS
1 stop5h 08m
Delta
Deal found 1/31![Delta logo]()
$509
Find flight deals from Chicago to Fort Walton Beach
Keep the following information in mind while searching for Chicago to Fort Walton Beach flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Kiwi.com) |
One-way from | $119 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $243 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Fort Walton Beach 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 Chicago to Fort Walton Beach that are best for you.
Fly from
Chicago
Fly to
Fort Walton Beach
Route
Depart
Return
Price
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Thu 2/26
3:40 pm-5:46 pm
Nonstop2h 06m
Valparaiso Destin-Ft Walton Beach
Sun 3/1
12:31 pm-2:50 pm
Nonstop2h 19m
$227
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Thu 3/12
7:30 am-1:50 pm
1 stop6h 20m
Valparaiso Destin-Ft Walton Beach
Sun 3/15
5:37 pm-7:53 pm
Nonstop2h 16m
$254
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sat 4/18
4:20 pm-9:00 pm
1 stop4h 40m
Valparaiso Destin-Ft Walton Beach
Sat 4/25
12:10 pm-6:15 pm
1 stop6h 05m
$278
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Tue 3/3
8:15 am-1:20 pm
1 stop5h 05m
Valparaiso Destin-Ft Walton Beach
Sat 3/7
4:40 pm-12:05 am
1 stop7h 25m
$307
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sat 5/2
1:55 pm-9:00 pm
1 stop7h 05m
Valparaiso Destin-Ft Walton Beach
Wed 5/6
7:15 am-12:50 pm
1 stop5h 35m
$307
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Tue 3/31
12:47 pm-6:39 pm
1 stop5h 52m
Valparaiso Destin-Ft Walton Beach
Tue 4/7
6:00 am-9:56 am
1 stop3h 56m
$335
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Tue 3/31
11:00 am-9:15 pm
2 stops10h 15m
Valparaiso Destin-Ft Walton Beach
Tue 4/7
7:15 am-2:55 pm
2 stops7h 40m
$346
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Thu 5/28
5:30 am-9:20 am
1 stop3h 50m
Valparaiso Destin-Ft Walton Beach
Sat 6/6
11:40 am-7:35 pm
1 stop7h 55m
$347
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sat 5/16
4:30 pm-10:53 pm
1 stop6h 23m
Valparaiso Destin-Ft Walton Beach
Thu 5/21
6:00 am-9:51 am
1 stop3h 51m
$354
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sat 4/25
5:59 pm-11:19 pm
1 stop5h 20m
Valparaiso Destin-Ft Walton Beach
Mon 4/27
1:53 pm-8:16 pm
1 stop6h 23m
$354
Showing 1-10 of 32 results
Best time to book a flight from Chicago to Fort Walton Beach
Have a flexible travel schedule? Discover the best time to fly to Fort Walton Beach from Chicago with our price prediction graph.
MDW-VPS
ORD-VPS
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 Chicago to Fort Walton Beach
CHI-FO9
MDW-VPS
ORD-VPS
How far ahead should I book a flight from Chicago to Fort Walton Beach?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Walton Beach. Price data was last updated on January 30, 2026.
The best time to book flights from Chicago to Fort Walton Beach is 17 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Fort Walton Beach?
Currently, July is the cheapest month in which you can book a flight from Chicago to Fort Walton Beach (average of $81). Flying from Chicago to Fort Walton Beach in December 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 CHI to FO9?
Find hourly flight availability from Chicago to Fort Walton Beach. 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 Chicago to Fort Walton Beach is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 11% on airfare.
Weekly flight availability from Chicago to Fort Walton Beach
Explore weekly flight availability from Chicago to Fort Walton Beach. 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 CHI to FO9 are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
Reviews of airlines servicing Fort Walton Beach
Get insights into the airlines that provide service to Fort Walton Beach. 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 Fort Walton Beach. Reviews last updated February 3, 2026.
Read through reviews of airlines operating flights from Chicago to Fort Walton Beach, such as Southwest, Delta, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Fort Walton Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Fort Walton Beach
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Chicago to Fort Walton Beach
Discover the top 6 airlines that operate flights from Chicago to Fort Walton Beach. 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$82 | Average$168 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$116 | Average$210 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$133 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$406 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$209 | Average$404 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$363 | FlexibilityNo cancel fee | On-time63% |