$112+ Cheap flights from Chicago (CHI) to Pensacola (PNS)
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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Oct 14 — Oct 211
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Pensacola with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Pensacola are usually found in November or February, booked 38 days in advance, depart on a Wednesday or Tuesday and return on a Friday
Cheap flight deals from Chicago to Pensacola
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Cheapest flights from Chicago to PensacolaExplore the most affordable flight options available from Chicago to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
Explore the most affordable flight options available from Chicago to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
1 stop8h 01m
Fri 10/233:26 pm -
1 stop8h 58m
Deal found 9/10![Frontier logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/77:11 am -
1 stop11h 54m
Wed 10/147:45 pm -
1 stop19h 45m
Deal found 9/9![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/186:30 am -
1 stop8h 01m
Wed 10/217:45 pm -
1 stop19h 45m
Deal found 9/12![Multiple Airlines logo]()
$294
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Wed 9/233:50 pm -
1 stop21h 24m
Mon 9/283:26 pm -
1 stop8h 57m
Deal found 9/10![Frontier logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/77:11 am -
1 stop11h 54m
Tue 10/131:20 pm -
2 stops22h 12m
Deal found 9/10![Multiple Airlines logo]()
$296
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:50 pm -
1 stop21h 24m
Thu 9/243:26 pm -
1 stop8h 57m
Deal found 9/10![Frontier logo]()
$298
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/57:30 am -
Nonstop2h 29m
Mon 11/92:34 pm -
Nonstop2h 55m
Deal found 9/10![American Airlines logo]()
$299
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:30 am -
1 stop8h 01m
Fri 10/23:26 pm -
1 stop8h 57m
Deal found 9/13![Frontier logo]()
$300
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:30 am -
1 stop8h 01m
Thu 10/13:26 pm -
1 stop8h 57m
Deal found 9/10![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/256:30 am -
1 stop8h 01m
Fri 10/301:25 pm -
2 stops26h 12m
Deal found 9/13![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/108:04 am -
1 stop11h 01m
Tue 10/137:10 pm -
1 stop20h 20m
Deal found 9/10![Multiple Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sun 10/116:04 am -
1 stop6h 30m
Sat 10/175:40 pm -
1 stop4h 53m
Deal found 9/10![Delta logo]()
$319
Best flights from Chicago to PensacolaDiscover carefully curated flight deals from Chicago to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
Discover carefully curated flight deals from Chicago to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/116:49 am -
1 stop5h 51m
Sun 11/156:14 pm -
1 stop5h 40m
Deal found 9/9![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:57 am -
Nonstop2h 29m
Mon 11/232:22 pm -
Nonstop2h 40m
Deal found 9/9![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/26:05 pm -
1 stop4h 45m
Mon 10/56:05 pm -
1 stop5h 50m
Deal found 9/10![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 12/311:35 am -
1 stop5h 35m
Tue 12/85:44 pm -
1 stop6h 08m
Deal found 9/10![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/138:05 am -
1 stop3h 55m
Tue 10/204:10 pm -
2 stops7h 40m
Deal found 9/9![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/56:05 am -
1 stop4h 34m
Sat 10/105:40 pm -
1 stop4h 53m
Deal found 9/13![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/2111:45 am -
1 stop3h 40m
Thu 10/226:05 pm -
1 stop5h 50m
Deal found 9/13![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/105:13 pm -
1 stop6h 28m
Sun 11/156:00 am -
1 stop4h 24m
Deal found 9/12![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:45 am -
Nonstop2h 29m
Sat 10/104:54 pm -
1 stop6h 33m
Deal found 9/13![United Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/78:00 am -
2 stops9h 20m
Sat 1/237:30 am -
2 stops9h 45m
Deal found 9/11![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/266:05 am -
1 stop4h 34m
Sat 10/39:26 am -
1 stop5h 58m
Deal found 9/12![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:05 am -
Nonstop2h 29m
Sat 10/34:18 pm -
Nonstop2h 42m
Deal found 9/13![United Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/166:05 pm -
1 stop4h 50m
Mon 10/196:05 pm -
1 stop5h 50m
Deal found 9/11![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/238:05 am -
1 stop6h 57m
Thu 10/16:00 am -
1 stop6h 41m
Deal found 9/10![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:22 pm -
1 stop7h 18m
Sat 12/55:45 pm -
Nonstop2h 47m
Deal found 9/12![United Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/266:05 am -
1 stop4h 34m
Mon 9/284:07 pm -
1 stop6h 37m
Deal found 9/12![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/304:11 pm -
1 stop5h 59m
Mon 10/54:18 pm -
Nonstop2h 42m
Deal found 9/14![United Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:00 am -
1 stop9h 14m
Tue 10/64:18 pm -
Nonstop2h 42m
Deal found 9/13![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/198:05 am -
1 stop6h 57m
Tue 9/225:30 pm -
1 stop6h 29m
Deal found 9/10![Delta logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:10 pm -
1 stop8h 00m
Wed 10/282:22 pm -
Nonstop2h 43m
Deal found 9/10![United Airlines logo]()
$499
Last-minute flights from Chicago to PensacolaDiscover last-minute flight deals from Chicago to Pensacola. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pensacola. Data last updated September 14, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:50 pm -
1 stop21h 24m
Thu 9/243:26 pm -
1 stop8h 57m
Deal found 9/10![Frontier logo]()
$298
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Wed 9/233:50 pm -
1 stop21h 24m
Mon 9/283:26 pm -
1 stop8h 57m
Deal found 9/10![Frontier logo]()
$295
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:30 am -
1 stop8h 01m
Thu 10/13:26 pm -
1 stop8h 57m
Deal found 9/10![Frontier logo]()
$301
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:30 am -
1 stop8h 01m
Fri 10/23:26 pm -
1 stop8h 57m
Deal found 9/13![Frontier logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/77:11 am -
1 stop11h 54m
Wed 10/147:45 pm -
1 stop19h 45m
Deal found 9/9![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/77:11 am -
1 stop11h 54m
Tue 10/131:20 pm -
2 stops22h 12m
Deal found 9/10![Multiple Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sun 10/116:04 am -
1 stop6h 30m
Sat 10/175:40 pm -
1 stop4h 53m
Deal found 9/10![Delta logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
1 stop10h 26m
Mon 10/198:15 pm -
2 stops15h 17m
Deal found 9/9![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
1 stop10h 26m
Wed 10/211:25 pm -
2 stops19h 56m
Deal found 9/9![Multiple Airlines logo]()
$303
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
1 stop8h 01m
Fri 10/233:26 pm -
1 stop8h 58m
Deal found 9/10![Frontier logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/256:30 am -
1 stop8h 01m
Fri 10/301:25 pm -
2 stops26h 12m
Deal found 9/13![Multiple Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:57 am -
Nonstop2h 29m
Tue 11/102:22 pm -
Nonstop2h 40m
Deal found 9/10![United Airlines logo]()
$299
One-way flights from Chicago to PensacolaSearch for one-way flight options from Chicago to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
Search for one-way flight options from Chicago to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/138:05 am -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$112
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:50 pm -
1 stop21h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$116
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/207:45 am -
2 stops7h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$117
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:30 am -
1 stop8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$119
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:30 am -
1 stop8h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 am -
1 stop8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$121
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:30 am -
1 stop8h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$125
This Travelocity deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:40 am -
1 stop11h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:30 am -
1 stop8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:07 pm -
1 stop15h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
1 stop10h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:11 am -
1 stop11h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$138
Find flight deals from Chicago to Pensacola
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pensacola (PNS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Frontier) |
One-way from | $112 (Southwest) |
Popular in | June |
Cheapest in | November |
Average price | $367 |
Good round-trip deal | $299 or less |
Good one-way deal | $206 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Pensacola 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 7,457,451 searches. Data last updated September 14, 2026.
Use the filters below to find and compare flights from Chicago to Pensacola that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 10/13
8:05 am-12:00 pm
1 stop3h 55m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$112
Quickest round-trip
ChicagoPensacola
ORD Chicago O'Hare Intl - PNS Pensacola
ORDPNS
Chicago O'Hare Intl
Tue 10/20
11:05 am-1:34 pm
Nonstop2h 29m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$150
ChicagoPensacola
ORD Chicago O'Hare Intl - PNS Pensacola
ORDPNS
Chicago O'Hare Intl
Thu 12/10
6:15 pm-11:39 pm
1 stop5h 24m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Sat 3/6
6:00 am-12:51 pm
1 stop6h 51m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 9/30
2:45 pm-6:40 pm
1 stop3h 55m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Sun 12/6
6:00 am-12:44 pm
1 stop6h 44m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 10/13
6:04 am-12:34 pm
1 stop6h 30m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
ChicagoPensacola
ORD Chicago O'Hare Intl - PNS Pensacola
ORDPNS
Chicago O'Hare Intl
Wed 12/9
8:04 am-12:44 pm
1 stop4h 40m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoPensacola
ORD Chicago O'Hare Intl - PNS Pensacola
ORDPNS
Chicago O'Hare Intl
Wed 12/2
10:32 am-5:57 pm
1 stop7h 25m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoPensacola
ORD Chicago O'Hare Intl - PNS Pensacola
ORDPNS
Chicago O'Hare Intl
Tue 10/13
6:30 am-12:34 pm
1 stop6h 04m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Chicago to Pensacola
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Pensacola in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Pensacola flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Pensacola flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Pensacola flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Pensacola
Have a flexible travel schedule? Discover the best time to fly to Pensacola from Chicago with our price prediction graph.
CHI-PNS
ORD-PNS
MDW-PNS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Pensacola
CHI-PNS
ORD-PNS
MDW-PNS
What is the cheapest month to book a flight from Chicago to Pensacola?
Currently, February is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $305). Flying from Chicago to Pensacola in July is currently the most expensive (average of $428). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to PNS?
Find hourly flight availability from Chicago to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2026.
One of the essential ways to save on airfare from Chicago to Pensacola is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 15% on airfare.
Weekly flight availability from Chicago to Pensacola
Explore weekly flight availability from Chicago to Pensacola. 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 September 14, 2026.
The most flights from CHI to PNS are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chicago to Pensacola?
Airfare is below average for this route at the moment.
Chicago to Pensacola flights typically cost between $301 and $441 in October.The cheapest round-trip price found within the last 5 days was $291 on Frontier (Oct 22-Oct 23).
How far ahead should I book a flight from Chicago to Pensacola?
The price you pay for your flight from Chicago to Pensacola may vary depending on when you book. For the best chance of a lower fare, look to book 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Pensacola
Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated September 14, 2026.
Read through reviews of airlines operating flights from Chicago to Pensacola, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Pensacola. 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 Pensacola?
Book flights to Pensacola if you plan to visit one of these locationsNavarre
Gulf Breeze
Foley
Atmore
Navarre Beach
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Chicago and Pensacola flights
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Top 4 airlines flying from Chicago to Pensacola
Discover the top 4 airlines that operate flights from Chicago to Pensacola. 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 7,457,451 searches. Data last updated September 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$295 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$228 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$282 | Average$403 | FlexibilityNo cancel fee | On-time63% |