$78+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Jun 5 — Jun 121
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 May 6, 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 May 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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 6/196:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 9/184:01 pm
VPS
- MDW
Nonstop2h 18m
Allegiant Air
Mon 9/218:08 pm
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$138
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 5/105:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/158:23 pm
VPS
- MDW
2 stops25h 48m
Multiple Airlines
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/237:58 pm
VPS
- MDW
1 stop17h 59m
Allegiant Air
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 6/16:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Mon 6/89:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Mon 6/158:23 pm
VPS
- MDW
2 stops38h 46m
Multiple Airlines
Mon 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/17:51 pm
VPS
- MDW
2 stops39h 18m
Multiple Airlines
Mon 6/89:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/228:23 pm
VPS
- ORD
2 stops23h 27m
Multiple Airlines
Sat 7/46:19 pm
ORD
- VPS
1 stop22h 44m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$318
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 May 6, 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 May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Sun 5/3112:27 pm
MDW
- VPS
2 stops30h 34m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 5/4. 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 5/287:20 am
VPS
- MDW
1 stop4h 50m
Southwest
Tue 6/27:00 am
MDW
- VPS
1 stop6h 10m
Southwest
Deal found 5/4![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 5/3. 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.
Wed 5/277:06 am
VPS
- ORD
1 stop6h 41m
Delta
Fri 5/2911:26 am
ORD
- VPS
1 stop5h 14m
Delta
Deal found 5/3![Delta logo]()
$393
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:20 am
VPS
- ORD
Nonstop2h 43m
American Airlines
Thu 6/47:10 am
ORD
- VPS
1 stop5h 09m
American Airlines
Deal found 5/1![American Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 5/1. 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 5/2812:35 pm
VPS
- MDW
1 stop4h 25m
Southwest
Thu 6/42:45 pm
MDW
- VPS
1 stop4h 30m
Southwest
Deal found 5/1![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 5/1. 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.
Thu 5/282:55 pm
VPS
- ORD
1 stop5h 31m
Delta
Thu 6/47:07 am
ORD
- VPS
1 stop6h 53m
Delta
Deal found 5/1![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1511:13 am
VPS
- ORD
Nonstop2h 41m
American Airlines
Mon 6/228:15 am
ORD
- VPS
Nonstop2h 28m
American Airlines
Deal found 5/3![American Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:30 am
VPS
- MDW
1 stop4h 50m
Southwest
Thu 9/35:55 am
MDW
- VPS
1 stop3h 40m
Southwest
Deal found 5/3![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:00 am
VPS
- ORD
1 stop5h 36m
Delta
Thu 7/91:44 pm
ORD
- VPS
1 stop4h 58m
Delta
Deal found 5/5![Delta logo]()
$414
This American Airlines deal was found by Cheapflights users on 5/5. 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 8/285:59 pm
VPS
- ORD
1 stop5h 58m
American Airlines
Sun 8/308:29 am
ORD
- VPS
Nonstop2h 31m
American Airlines
Deal found 5/5![American Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 6/2212:30 pm
VPS
- MDW
1 stop4h 10m
Southwest
Sat 7/411:55 am
MDW
- VPS
1 stop5h 15m
Southwest
Deal found 5/1![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 5/6. 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 7/19:19 am
VPS
- MDW
1 stop6h 21m
Delta
Thu 7/911:05 am
MDW
- VPS
1 stop5h 16m
Delta
Deal found 5/6![Delta logo]()
$414
This Southwest deal was found by Cheapflights users on 5/5. 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 5/5![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:45 pm
VPS
- ORD
1 stop6h 14m
Delta
Mon 6/86:30 am
ORD
- VPS
1 stop6h 40m
Delta
Deal found 5/4![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 5/5. 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 8/52:11 pm
VPS
- ORD
1 stop7h 36m
Delta
Sun 8/98:02 am
ORD
- VPS
1 stop5h 58m
Delta
Deal found 5/5![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 5/4. 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 5/197:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sat 5/231:55 pm
ORD
- VPS
1 stop7h 10m
Southwest
Deal found 5/4![Southwest logo]()
$441
This Delta deal was found by Cheapflights users on 5/5. 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 8/56:00 am
VPS
- MDW
1 stop3h 59m
Delta
Sun 8/912:46 pm
MDW
- VPS
1 stop5h 51m
Delta
Deal found 5/5![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Tue 5/192:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 5/1![Southwest logo]()
$441
Last-minute flights from Fort Walton Beach to ChicagoDiscover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Walton Beach to Chicago. Data last updated May 6, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 5/105:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/237:58 pm
VPS
- MDW
1 stop17h 59m
Allegiant Air
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/238:24 pm
VPS
- MDW
2 stops25h 38m
Multiple Airlines
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Sun 5/3112:27 pm
MDW
- VPS
2 stops30h 34m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$296
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 6/16:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Mon 6/89:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/17:51 pm
VPS
- MDW
2 stops39h 18m
Multiple Airlines
Mon 6/89:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$289
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/158:23 pm
VPS
- MDW
2 stops25h 48m
Multiple Airlines
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Mon 6/158:23 pm
VPS
- MDW
2 stops38h 46m
Multiple Airlines
Mon 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/228:23 pm
VPS
- ORD
2 stops23h 27m
Multiple Airlines
Sat 7/46:19 pm
ORD
- VPS
1 stop22h 44m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$318
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$153
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 May 6, 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 May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$78
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 8/38:39 pm
VPS
- ORD
2 stops35h 14m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 5/144:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/158:23 pm
VPS
- ORD
2 stops35h 40m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/158:23 pm
VPS
- MDW
2 stops25h 48m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/296:15 am
VPS
- ORD
2 stops13h 26m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 5/308:24 pm
VPS
- ORD
2 stops35h 31m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/17:51 pm
VPS
- ORD
2 stops36h 04m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/207:12 pm
VPS
- MDW
1 stop18h 44m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/5. 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
Deal found 5/5![Allegiant Air logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/281:04 pm
VPS
- ORD
1 stop31h 39m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$161
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $107 (Cheapflightsfares) |
One-way from | $78 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $103 |
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 May 6, 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
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 5/29
6:21 pm-8:40 pm
Nonstop2h 19m
Chicago Midway
Sun 5/31
12:27 pm-7:01 pm
2 stops30h 34m
$296
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 5/28
7:20 am-12:10 pm
1 stop4h 50m
Chicago Midway
Tue 6/2
7:00 am-1:10 pm
1 stop6h 10m
$374
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 5/28
12:35 pm-5:00 pm
1 stop4h 25m
Chicago Midway
Thu 6/4
2:45 pm-7:15 pm
1 stop4h 30m
$389
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 5/27
7:06 am-1:47 pm
1 stop6h 41m
Chicago O'Hare Intl
Fri 5/29
11:26 am-4:40 pm
1 stop5h 14m
$393
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 5/28
2:55 pm-8:26 pm
1 stop5h 31m
Chicago O'Hare Intl
Thu 6/4
7:07 am-2:00 pm
1 stop6h 53m
$399
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 5/28
11:20 am-2:03 pm
Nonstop2h 43m
Chicago O'Hare Intl
Thu 6/4
7:10 am-12:19 pm
1 stop5h 09m
$405
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 8/26
10:30 am-3:20 pm
1 stop4h 50m
Chicago Midway
Thu 9/3
5:55 am-9:35 am
1 stop3h 40m
$407
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 6/22
12:30 pm-4:40 pm
1 stop4h 10m
Chicago Midway
Sat 7/4
11:55 am-5:10 pm
1 stop5h 15m
$408
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/1
7:00 am-12:36 pm
1 stop5h 36m
Chicago O'Hare Intl
Thu 7/9
1:44 pm-6:42 pm
1 stop4h 58m
$414
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 7/1
9:19 am-3:40 pm
1 stop6h 21m
Chicago Midway
Thu 7/9
11:05 am-4:21 pm
1 stop5h 16m
$414
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 May 6, 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 51% 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 May 6, 2026.
The most flights from FO9 to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 May 6, 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.
Overall
7.9
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
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 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 May 6, 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 May 6, 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 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$157 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$173 | Average$213 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$196 | Average$291 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$343 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$228 | Average$385 | FlexibilityNo cancel fee | On-time63% |