$83+ Cheap flights from Fort Walton Beach, FL to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Apr 22 — Apr 291
Round-trip
1 adult, Economy
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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 March 23, 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 March 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Thu 4/234:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/21![Allegiant Air logo]()
$83
This Booking.com deal was found by Cheapflights users on 3/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/22![Allegiant Air logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/75:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/18![Allegiant Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/237:30 am
VPS
- MDW
1 stop29h 30m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Thu 4/167:30 am
VPS
- MDW
1 stop29h 30m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Wed 5/68:30 am
VPS
- ORD
2 stops25h 01m
Multiple Airlines
Sat 5/912:53 pm
ORD
- VPS
1 stop24h 57m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/237:30 am
VPS
- ORD
1 stop28h 12m
Multiple Airlines
Mon 4/275:50 am
ORD
- VPS
2 stops26h 58m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Sat 4/187:58 pm
VPS
- ORD
2 stops50h 41m
Multiple Airlines
Sat 4/2512:53 pm
ORD
- VPS
1 stop24h 57m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 3/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2611:17 am
VPS
- ORD
Nonstop2h 43m
American Airlines
Tue 6/28:12 am
ORD
- VPS
Nonstop2h 35m
American Airlines
Deal found 3/22![American Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Sat 5/210:08 am
VPS
- ORD
2 stops24h 15m
Multiple Airlines
Sat 5/912:53 pm
ORD
- VPS
1 stop24h 57m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Tue 6/22:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 3/17![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 3/19. 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.
Wed 4/157:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sat 4/181:55 pm
ORD
- VPS
1 stop7h 05m
Southwest
Deal found 3/19![Southwest logo]()
$374
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 March 23, 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 March 23, 2026.
This Booking.com deal was found by Cheapflights users on 3/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/22![Allegiant Air logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Thu 4/167:30 am
VPS
- MDW
1 stop29h 30m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2911:32 am
VPS
- ORD
Nonstop2h 45m
American Airlines
Mon 8/38:26 am
ORD
- VPS
Nonstop2h 36m
American Airlines
Deal found 3/17![American Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 3/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:40 pm
VPS
- MDW
1 stop7h 05m
Delta
Sat 7/256:00 am
MDW
- VPS
1 stop4h 11m
Delta
Deal found 3/20![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 3/19. 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.
Wed 4/157:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sat 4/186:00 am
ORD
- VPS
2 stops15h 00m
Southwest
Deal found 3/19![Southwest logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Mon 4/138:00 am
VPS
- MDW
2 stops35h 31m
Multiple Airlines
Thu 4/167:12 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 3/21. 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 5/167:00 am
VPS
- ORD
1 stop8h 30m
Southwest
Tue 5/1911:55 am
ORD
- VPS
2 stops9h 05m
Southwest
Deal found 3/21![Southwest logo]()
$385
This American Airlines deal was found by Cheapflights users on 3/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:13 am
VPS
- ORD
1 stop7h 07m
American Airlines
Thu 7/98:26 am
ORD
- VPS
Nonstop2h 36m
American Airlines
Deal found 3/22![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 3/18. 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.
Wed 7/12:40 pm
VPS
- ORD
1 stop4h 21m
Delta
Thu 7/97:10 am
ORD
- VPS
1 stop5h 15m
Delta
Deal found 3/18![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 3/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:40 pm
VPS
- ORD
1 stop4h 21m
Delta
Mon 8/35:55 pm
ORD
- VPS
1 stop5h 13m
Delta
Deal found 3/17![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 3/21. 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 4/2511:05 am
VPS
- MDW
1 stop6h 45m
Southwest
Sun 4/266:55 am
MDW
- VPS
2 stops8h 20m
Southwest
Deal found 3/21![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 3/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:05 pm
VPS
- MDW
1 stop4h 40m
Delta
Mon 8/35:25 pm
MDW
- VPS
1 stop5h 43m
Delta
Deal found 3/17![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:30 pm
VPS
- MDW
1 stop5h 05m
Southwest
Mon 8/31:00 pm
MDW
- VPS
2 stops8h 05m
Southwest
Deal found 3/17![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 3/21. 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 4/257:00 am
VPS
- ORD
2 stops14h 55m
Southwest
Sun 4/262:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/21![Southwest logo]()
$405
This Delta deal was found by Cheapflights users on 3/19. 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.
Thu 4/236:00 am
VPS
- MDW
1 stop3h 56m
Delta
Mon 4/276:00 am
MDW
- VPS
1 stop6h 47m
Delta
Deal found 3/19![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Sun 4/262:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/18![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 3/18. 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.
Fri 4/175:05 pm
VPS
- MDW
1 stop5h 23m
Delta
Sun 4/196:00 am
MDW
- VPS
1 stop4h 59m
Delta
Deal found 3/18![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 3/19. 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 4/244:05 pm
VPS
- MDW
1 stop5h 50m
Southwest
Mon 4/2710:15 am
MDW
- VPS
1 stop7h 00m
Southwest
Deal found 3/19![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 3/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:55 am
VPS
- ORD
1 stop6h 40m
Delta
Sun 4/195:15 am
ORD
- VPS
1 stop5h 44m
Delta
Deal found 3/20![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 3/19. 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.
Tue 5/267:15 am
VPS
- ORD
2 stops11h 10m
Southwest
Tue 6/211:55 am
ORD
- VPS
2 stops9h 05m
Southwest
Deal found 3/19![Southwest logo]()
$418
Last-minute flights from Fort Walton Beach to ChicagoDiscover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated March 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/19. 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.
Wed 4/157:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sat 4/181:55 pm
ORD
- VPS
1 stop7h 05m
Southwest
Deal found 3/19![Southwest logo]()
$374
This Booking.com deal was found by Cheapflights users on 3/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/22![Allegiant Air logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Thu 4/167:30 am
VPS
- MDW
1 stop29h 30m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Sat 4/187:58 pm
VPS
- ORD
2 stops50h 41m
Multiple Airlines
Sat 4/2512:53 pm
ORD
- VPS
1 stop24h 57m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Tue 4/282:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 3/18![Southwest logo]()
$373
This American Airlines deal was found by Cheapflights users on 3/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Tue 4/289:41 am
ORD
- VPS
Nonstop2h 34m
American Airlines
Deal found 3/18![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 3/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Mon 4/279:41 am
ORD
- VPS
Nonstop2h 34m
American Airlines
Deal found 3/18![American Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Thu 4/234:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/21![Allegiant Air logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/237:30 am
VPS
- MDW
1 stop29h 30m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/237:30 am
VPS
- ORD
1 stop28h 12m
Multiple Airlines
Mon 4/275:50 am
ORD
- VPS
2 stops26h 58m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$322
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/75:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/18![Allegiant Air logo]()
$118
This Sun Country Air deal was found by Cheapflights users on 3/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:07 pm
VPS
- ORD
1 stop24h 59m
Sun Country Air
Thu 5/78:06 pm
ORD
- VPS
1 stop15h 00m
Sun Country Air
Deal found 3/20![Sun Country Air logo]()
$366
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 March 23, 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 March 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Thu 4/237:30 am
VPS
- ORD
1 stop28h 12m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/187:58 pm
VPS
- ORD
2 stops38h 25m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 5/211:07 pm
VPS
- ORD
1 stop7h 30m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Thu 4/168:16 am
VPS
- ORD
2 stops38h 38m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 6/213:12 pm
VPS
- MDW
1 stop28h 18m
Allegiant Air
Deal found 3/19![Allegiant Air logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Fri 4/177:36 pm
VPS
- ORD
2 stops51h 03m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 5/188:00 am
VPS
- ORD
2 stops40h 27m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$167
This Southwest deal was found by Cheapflights users on 3/21. 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.
Wed 5/612:30 pm
VPS
- MDW
1 stop4h 15m
Southwest
Deal found 3/21![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Wed 5/68:30 am
VPS
- MDW
2 stops13h 32m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Fri 4/247:36 pm
VPS
- MDW
2 stops36h 50m
Allegiant Air
Deal found 3/21![Allegiant Air logo]()
$196
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:20 am
VPS
- MDW
1 stop4h 50m
Southwest
Deal found 3/22![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 3/21. 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.
Thu 9/102:00 pm
VPS
- MDW
2 stops7h 00m
Southwest
Deal found 3/21![Southwest logo]()
$211
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 March 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $83 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $345 |
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 March 23, 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
Thu 4/16
4:05 pm-6:22 pm
Nonstop2h 17m
Chicago Midway
Sun 4/26
5:47 pm-7:56 pm
Nonstop2h 09m
$104
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 4/16
7:30 am-1:00 pm
1 stop29h 30m
Chicago Midway
Sun 4/26
5:47 pm-7:56 pm
Nonstop2h 09m
$202
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 4/13
8:00 am-7:31 pm
2 stops35h 31m
Chicago Midway
Thu 4/16
7:12 pm-9:21 pm
Nonstop2h 09m
$331
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/29
11:32 am-2:17 pm
Nonstop2h 45m
Chicago O'Hare Intl
Mon 8/3
8:26 am-11:02 am
Nonstop2h 36m
$375
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Tue 7/21
2:40 pm-9:45 pm
1 stop7h 05m
Chicago Midway
Sat 7/25
6:00 am-10:11 am
1 stop4h 11m
$375
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 4/15
7:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Sat 4/18
6:00 am-9:00 pm
2 stops15h 00m
$385
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Sat 5/16
7:00 am-3:30 pm
1 stop8h 30m
Chicago O'Hare Intl
Tue 5/19
11:55 am-9:00 pm
2 stops9h 05m
$385
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/1
7:13 am-2:20 pm
1 stop7h 07m
Chicago O'Hare Intl
Thu 7/9
8:26 am-11:02 am
Nonstop2h 36m
$385
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/1
2:40 pm-7:01 pm
1 stop4h 21m
Chicago O'Hare Intl
Thu 7/9
7:10 am-12:25 pm
1 stop5h 15m
$394
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/29
2:40 pm-7:01 pm
1 stop4h 21m
Chicago O'Hare Intl
Mon 8/3
5:55 pm-11:08 pm
1 stop5h 13m
$394
Showing 1-10 of 39 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 month to book a flight from Fort Walton Beach to Chicago?
Currently, June is the cheapest month in which you can book a flight from Fort Walton Beach to Chicago (average of $112). Flying from Fort Walton Beach to Chicago in December is currently the most expensive (average of $228). 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 March 23, 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 36% 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 March 23, 2026.
The most flights from FO9 to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 March 23, 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.
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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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 March 23, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Fort Walton Beach and Chicago flights
Browse other Fort Walton Beach and Chicago flight options. Last updated on March 23, 2026.
Popular flight searches
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Fort Walton Beach to Chicago flights
Consider these flights traveling from Fort Walton Beach to Chicago.
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 March 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$157 | Average$350 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$161 | Average$201 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$196 | Average$277 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$312 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$216 | Average$369 | FlexibilityNo cancel fee | On-time63% |