$62+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Jul 22 — Jul 291
Round-trip
1 adult, Economy
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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 June 22, 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 June 22, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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.
Mon 8/106:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 8/179:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$104
This Gotogate deal was found by Cheapflights users on 6/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 8/179:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Mon 7/276:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Fri 7/319:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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.
Mon 8/36:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Fri 8/79:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Mon 7/206:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Fri 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/316:11 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Mon 8/109:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/68:48 pm
VPS
- MDW
1 stop18h 11m
Allegiant Air
Fri 8/79:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/17:21 pm
VPS
- MDW
1 stop18h 37m
Allegiant Air
Mon 8/109:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Mon 6/296:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Fri 7/39:15 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/23:08 pm
VPS
- MDW
1 stop23h 30m
Allegiant Air
Mon 8/109:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:25 am
VPS
- ORD
2 stops29h 50m
Multiple Airlines
Thu 7/237:25 am
ORD
- VPS
1 stop9h 38m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/109:07 pm
VPS
- ORD
1 stop32h 30m
Multiple Airlines
Mon 8/177:15 am
ORD
- VPS
1 stop13h 02m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$336
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 June 22, 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 June 22, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Mon 8/106:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 8/179:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/124:07 pm
VPS
- MDW
2 stops29h 56m
Multiple Airlines
Fri 8/149:25 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 6/21. 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 8/293:00 pm
VPS
- MDW
1 stop4h 20m
Southwest
Tue 9/12:40 pm
MDW
- VPS
1 stop6h 25m
Southwest
Deal found 6/21![Southwest logo]()
$353
This Sun Country Air deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:05 pm
VPS
- ORD
1 stop23h 19m
Sun Country Air
Sun 8/96:25 pm
ORD
- VPS
1 stop22h 38m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$364
This Delta deal was found by Cheapflights users on 6/19. 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 11/242:40 pm
VPS
- ORD
1 stop6h 30m
Delta
Tue 12/17:10 am
ORD
- VPS
1 stop4h 03m
Delta
Deal found 6/19![Delta logo]()
$395
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/234:53 pm
VPS
- ORD
1 stop5h 07m
American Airlines
Sun 7/266:30 am
ORD
- VPS
1 stop5h 32m
American Airlines
Deal found 6/19![American Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/2712:00 pm
VPS
- MDW
2 stops34h 03m
Multiple Airlines
Fri 7/319:21 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/108:39 am
VPS
- MDW
2 stops13h 24m
Multiple Airlines
Mon 8/179:25 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 6/19. 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 11/187:45 am
VPS
- ORD
1 stop6h 28m
Delta
Wed 12/25:30 am
ORD
- VPS
1 stop5h 43m
Delta
Deal found 6/19![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 6/19. 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.
Mon 8/37:55 am
VPS
- MDW
2 stops8h 25m
Southwest
Tue 8/42:00 pm
MDW
- VPS
2 stops7h 05m
Southwest
Deal found 6/19![Southwest logo]()
$414
This Sun Country Air deal was found by Cheapflights users on 6/22. 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 8/66:03 pm
VPS
- ORD
1 stop23h 21m
Sun Country Air
Sun 8/96:25 pm
ORD
- VPS
1 stop22h 38m
Sun Country Air
Deal found 6/22![Sun Country Air logo]()
$424
This Delta deal was found by Cheapflights users on 6/18. 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 7/185:06 pm
VPS
- ORD
1 stop6h 47m
Delta
Sat 7/255:30 am
ORD
- VPS
1 stop4h 59m
Delta
Deal found 6/18![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 6/20. 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 9/182:00 pm
VPS
- MDW
1 stop6h 10m
Southwest
Mon 9/215:30 pm
MDW
- VPS
1 stop3h 30m
Southwest
Deal found 6/20![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 6/21. 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 9/222:47 pm
VPS
- ORD
1 stop6h 08m
Delta
Tue 9/295:30 am
ORD
- VPS
1 stop5h 28m
Delta
Deal found 6/21![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 6/19. 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 8/62:00 pm
VPS
- MDW
2 stops7h 00m
Southwest
Fri 8/75:30 pm
MDW
- VPS
1 stop3h 30m
Southwest
Deal found 6/19![Southwest logo]()
$420
This Delta deal was found by Cheapflights users on 6/21. 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 12/199:25 am
VPS
- ORD
1 stop7h 12m
Delta
Sun 12/275:55 pm
ORD
- VPS
1 stop5h 12m
Delta
Deal found 6/21![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 6/19. 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 9/257:25 am
VPS
- MDW
2 stops6h 30m
Southwest
Mon 9/285:30 am
MDW
- VPS
1 stop6h 25m
Southwest
Deal found 6/19![Southwest logo]()
$425
This Delta deal was found by Cheapflights users on 6/22. 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.
Tue 7/142:45 pm
VPS
- ORD
1 stop5h 48m
Delta
Tue 7/216:22 pm
ORD
- VPS
1 stop5h 07m
Delta
Deal found 6/22![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 6/21. 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 7/97:32 pm
VPS
- ORD
1 stop4h 21m
Delta
Thu 7/165:30 am
ORD
- VPS
1 stop4h 59m
Delta
Deal found 6/21![Delta logo]()
$891
Last-minute flights from Fort Walton Beach to ChicagoDiscover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated June 22, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Mon 6/296:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Fri 7/39:15 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/28:30 pm
VPS
- MDW
1 stop18h 08m
Allegiant Air
Mon 7/69:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$269
This Delta deal was found by Cheapflights users on 6/18. 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 7/185:06 pm
VPS
- ORD
1 stop6h 47m
Delta
Sat 7/255:30 am
ORD
- VPS
1 stop4h 59m
Delta
Deal found 6/18![Delta logo]()
$395
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Mon 7/206:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Fri 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/208:39 am
VPS
- MDW
2 stops13h 24m
Multiple Airlines
Fri 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Thu 7/232:48 pm
MDW
- VPS
3 stops56h 06m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:25 am
VPS
- ORD
2 stops29h 50m
Multiple Airlines
Thu 7/237:25 am
ORD
- VPS
1 stop9h 38m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 6/20. 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 7/2311:32 am
VPS
- ORD
Nonstop2h 42m
American Airlines
Tue 7/288:30 am
ORD
- VPS
Nonstop2h 32m
American Airlines
Deal found 6/20![American Airlines logo]()
$405
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Mon 7/276:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Fri 7/319:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/276:10 pm
VPS
- MDW
Nonstop2h 20m
Multiple Airlines
Fri 7/316:05 am
MDW
- VPS
3 stops27h 00m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/316:11 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Mon 8/109:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/316:11 pm
VPS
- MDW
Nonstop2h 20m
Multiple Airlines
Sun 8/96:05 am
MDW
- VPS
3 stops17h 12m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$339
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 June 22, 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 June 22, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 7/316:11 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$62
This Trip.com deal was found by Cheapflights users on 6/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:11 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/257:21 pm
VPS
- MDW
1 stop18h 37m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/206:25 am
VPS
- ORD
2 stops29h 50m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/308:30 pm
VPS
- MDW
1 stop18h 08m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/131:07 pm
VPS
- ORD
1 stop7h 45m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 9/133:47 pm
VPS
- ORD
2 stops27h 57m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 9/1710:56 am
VPS
- ORD
1 stop10h 39m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/176:25 am
VPS
- ORD
2 stops29h 50m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/163:13 pm
VPS
- ORD
2 stops45h 47m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$166
This Sun Country Air deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 pm
VPS
- ORD
1 stop23h 19m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/179:07 pm
VPS
- ORD
2 stops40h 29m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$169
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 June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $104 (Cheapflightsfares) |
One-way from | $62 (Cheapflightsfares) |
Popular in | June |
Cheapest in | October |
Average price | $471 |
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 June 22, 2026.
Use the filters below to find and compare flights from Fort Walton Beach to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 8/10
6:14 pm-8:35 pm
Nonstop2h 21m
Chicago Midway
Mon 8/17
9:25 pm-11:39 pm
Nonstop2h 14m
$104
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 8/12
4:07 pm-10:03 pm
2 stops29h 56m
Chicago Midway
Fri 8/14
9:25 pm-11:39 pm
Nonstop2h 14m
$291
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 7/27
12:00 pm-10:03 pm
2 stops34h 03m
Chicago Midway
Fri 7/31
9:21 pm-11:35 pm
Nonstop2h 14m
$296
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 8/10
8:39 am-10:03 pm
2 stops13h 24m
Chicago Midway
Mon 8/17
9:25 pm-11:39 pm
Nonstop2h 14m
$318
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 8/29
3:00 pm-7:20 pm
1 stop4h 20m
Chicago Midway
Tue 9/1
2:40 pm-9:05 pm
1 stop6h 25m
$353
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Sun 8/2
6:05 pm-5:24 pm
1 stop23h 19m
Chicago O'Hare Intl
Sun 8/9
6:25 pm-5:03 pm
1 stop22h 38m
$364
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 11/24
2:40 pm-9:10 pm
1 stop6h 30m
Chicago O'Hare Intl
Tue 12/1
7:10 am-11:13 am
1 stop4h 03m
$395
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 11/18
7:45 am-2:13 pm
1 stop6h 28m
Chicago O'Hare Intl
Wed 12/2
5:30 am-11:13 am
1 stop5h 43m
$395
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Sat 7/18
5:06 pm-11:53 pm
1 stop6h 47m
Chicago O'Hare Intl
Sat 7/25
5:30 am-10:29 am
1 stop4h 59m
$395
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 9/22
2:47 pm-8:55 pm
1 stop6h 08m
Chicago O'Hare Intl
Tue 9/29
5:30 am-10:58 am
1 stop5h 28m
$395
Showing 1-10 of 37 resultsSorted by cheapest first
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 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 June 22, 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 evening tend to be the most expensive. A flight at noon could potentially save you up to 47% 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 June 22, 2026.
The most flights from FO9 to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Fort Walton Beach to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 22, 2026.
Read through reviews of airlines operating flights from Fort Walton Beach to Chicago, such as Southwest,Allegiant Air, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Fort Walton Beach to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 22, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Fort Walton Beach to Chicago by cabin class
Find flights from Fort Walton Beach to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Fort Walton Beach and Chicago flights
Browse other Fort Walton Beach and Chicago flight options. Last updated on June 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fort Walton Beach to Chicago flights
Consider these flights traveling from Fort Walton Beach to Chicago.
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 June 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$152 | Average$393 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$188 | Average$307 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$400 | FlexibilityNo cancel fee | On-time63% |