$100+ Cheap flights from Pensacola (PNS) 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Pensacola to Chicago 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 Pensacola to Chicago are usually found in February or November, booked 67 days in advance, depart on a Friday or Wednesday and return on a Wednesday
Cheap flight deals from Pensacola to Chicago
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Cheapest flights from Pensacola to ChicagoExplore the most affordable flight options available from Pensacola to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Pensacola to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop6h 10m
Tue 11/178:50 am -
1 stop6h 45m
Deal found 9/14![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/225:15 pm -
1 stop7h 55m
Mon 10/264:30 pm -
1 stop4h 05m
Deal found 9/15![Southwest logo]()
$252
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:15 pm -
1 stop11h 36m
Fri 10/236:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$254
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:15 pm -
1 stop11h 16m
Sun 10/186:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$259
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Thu 10/223:26 pm -
1 stop8h 58m
Sun 10/256:30 am -
1 stop8h 01m
Deal found 9/15![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/308:06 pm -
1 stop12h 40m
Fri 11/66:30 am -
1 stop8h 03m
Deal found 9/15![Frontier logo]()
$261
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 10/207:55 am -
1 stop5h 30m
Fri 10/239:20 pm -
2 stops13h 20m
Deal found 9/13![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/306:05 pm -
1 stop5h 50m
Mon 11/24:00 pm -
1 stop4h 30m
Deal found 9/15![Southwest logo]()
$267
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:28 pm -
1 stop8h 53m
Sun 11/156:30 am -
1 stop8h 03m
Deal found 9/12![Frontier logo]()
$269
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:26 pm -
1 stop8h 57m
Tue 10/67:11 am -
1 stop11h 19m
Deal found 9/14![Multiple Airlines logo]()
$270
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:26 pm -
1 stop8h 58m
Sun 10/256:30 am -
1 stop8h 01m
Deal found 9/15![Frontier logo]()
$271
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:15 pm -
1 stop11h 16m
Fri 10/236:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$272
Best flights from Pensacola to ChicagoDiscover carefully curated flight deals from Pensacola to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Pensacola to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/226:05 pm -
2 stops7h 05m
Mon 10/264:30 pm -
1 stop4h 05m
Deal found 9/15![Southwest logo]()
$258
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 10/14:18 pm -
Nonstop2h 42m
Mon 10/510:45 am -
Nonstop2h 29m
Deal found 9/10![United Airlines logo]()
$299
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.
Thu 10/298:06 pm -
1 stop11h 48m
Sun 11/11:12 pm -
2 stops29h 59m
Deal found 9/10![Multiple Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/39:26 am -
1 stop5h 58m
Tue 10/65:09 pm -
1 stop6h 21m
Deal found 9/15![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/154:18 pm -
Nonstop2h 42m
Mon 10/1910:45 am -
Nonstop2h 29m
Deal found 9/15![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/226:05 pm -
2 stops7h 05m
Sun 10/253:00 pm -
2 stops6h 20m
Deal found 9/15![Southwest logo]()
$326
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:45 pm -
1 stop13h 33m
Wed 10/79:34 am -
1 stop26h 31m
Deal found 9/11![Multiple Airlines logo]()
$352
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.
Fri 10/25:36 pm -
1 stop6h 23m
Wed 10/76:30 am -
1 stop6h 04m
Deal found 9/12![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/2310:30 am -
1 stop4h 35m
Sun 10/255:00 am -
1 stop5h 25m
Deal found 9/15![Southwest logo]()
$330
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.
Thu 10/224:18 pm -
Nonstop2h 42m
Sun 10/2510:47 am -
Nonstop2h 28m
Deal found 9/12![United Airlines logo]()
$361
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:45 pm -
1 stop13h 33m
Thu 10/89:40 am -
2 stops46h 38m
Deal found 9/14![Multiple Airlines logo]()
$364
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/107:55 am -
1 stop5h 35m
Wed 4/147:30 am -
1 stop4h 55m
Deal found 9/12![Southwest logo]()
$339
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.
Mon 9/215:18 pm -
Nonstop2h 42m
Sun 9/2710:45 am -
Nonstop2h 29m
Deal found 9/10![United Airlines logo]()
$374
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:05 pm -
2 stops7h 05m
Mon 11/24:00 pm -
1 stop4h 30m
Deal found 9/12![Southwest logo]()
$344
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.
Sat 10/101:25 pm -
2 stops20h 15m
Mon 10/126:13 pm -
1 stop13h 55m
Deal found 9/13![Multiple Airlines logo]()
$403
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 11/132:15 pm -
2 stops8h 45m
Mon 11/167:05 am -
1 stop8h 30m
Deal found 9/11![Southwest logo]()
$350
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 10/24:18 pm -
Nonstop2h 42m
Mon 10/510:45 am -
Nonstop2h 29m
Deal found 9/13![United Airlines logo]()
$419
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.
Wed 12/97:55 am -
1 stop5h 00m
Sun 12/135:05 am -
2 stops8h 35m
Deal found 9/11![Southwest logo]()
$364
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.
Sat 10/32:16 pm -
1 stop7h 02m
Mon 10/510:45 am -
Nonstop2h 29m
Deal found 9/14![United Airlines logo]()
$434
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.
Thu 10/19:00 am -
1 stop7h 41m
Sat 10/310:45 am -
Nonstop2h 29m
Deal found 9/14![United Airlines logo]()
$454
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.
Mon 12/2812:23 pm -
1 stop20h 02m
Wed 12/3010:44 am -
1 stop20h 54m
Deal found 9/12![Multiple Airlines logo]()
$595
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.
Wed 9/235:10 pm -
1 stop7h 49m
Wed 9/3010:45 am -
Nonstop2h 29m
Deal found 9/13![United Airlines logo]()
$472
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.
Fri 10/94:54 pm -
1 stop7h 29m
Tue 10/1311:05 am -
Nonstop2h 29m
Deal found 9/10![United Airlines logo]()
$488
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.
Thu 10/159:00 am -
1 stop7h 41m
Sun 10/1810:45 am -
Nonstop2h 29m
Deal found 9/14![United Airlines logo]()
$495
Last-minute flights from Pensacola to ChicagoDiscover last-minute flight deals from Pensacola to Chicago. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Chicago. Data last updated September 16, 2026 and is based on user searches.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:11 pm -
1 stop8h 48m
Sun 9/276:30 am -
1 stop8h 01m
Deal found 9/10![Frontier logo]()
$260
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:26 pm -
1 stop8h 57m
Mon 10/56:30 am -
1 stop8h 01m
Deal found 9/10![Frontier logo]()
$242
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:11 pm -
1 stop8h 48m
Mon 10/56:30 am -
1 stop8h 01m
Deal found 9/12![Frontier logo]()
$280
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:26 pm -
1 stop8h 57m
Tue 10/67:11 am -
1 stop11h 19m
Deal found 9/14![Multiple Airlines logo]()
$270
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:26 pm -
1 stop8h 58m
Sat 10/176:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$279
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:15 pm -
1 stop11h 16m
Sun 10/186:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$259
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:15 pm -
1 stop11h 16m
Fri 10/236:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$272
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:15 pm -
1 stop11h 36m
Fri 10/236:30 am -
1 stop8h 01m
Deal found 9/11![Frontier logo]()
$254
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 10/207:55 am -
1 stop5h 30m
Fri 10/239:20 pm -
2 stops13h 20m
Deal found 9/13![Southwest logo]()
$263
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.
Thu 10/223:26 pm -
1 stop8h 58m
Sun 10/256:30 am -
1 stop8h 01m
Deal found 9/12![Frontier logo]()
$269
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 10/298:06 pm -
1 stop12h 40m
Sun 11/16:30 am -
1 stop8h 03m
Deal found 9/10![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/306:05 pm -
1 stop5h 50m
Mon 11/24:00 pm -
1 stop4h 30m
Deal found 9/15![Southwest logo]()
$267
One-way flights from Pensacola to ChicagoSearch for one-way flight options from Pensacola to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Pensacola to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/137:10 pm -
1 stop20h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/117:45 pm -
1 stop19h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$110
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:10 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$112
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 12/91:25 pm -
1 stop20h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$120
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:26 pm -
1 stop8h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$121
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.
Thu 10/13:26 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$122
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.
Thu 11/194:10 pm -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/47:45 pm -
1 stop19h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$127
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:26 pm -
1 stop8h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$128
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:55 am -
2 stops6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$129
This Super.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Fri 10/303:28 pm -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$129
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Fri 11/133:28 pm -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$130
Find flight deals from Pensacola to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to Chicago (CHI). 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 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $224 (Southwest) |
One-way from | $100 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $368 |
Good round-trip deal | $359 or less |
Good one-way deal | $234 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pensacola 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 7,457,451 searches. Data last updated September 16, 2026.
Use the filters below to find and compare flights from Pensacola to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 12/14
4:10 pm-10:40 pm
1 stop6h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$126
PensacolaChicago
PNS Pensacola - RFD Chicago Greater Rockford
PNSRFD
Pensacola
Sat 10/3
7:45 pm-9:18 am
1 stop13h 33m
Chicago Greater Rockford
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$151
PensacolaChicago
PNS Pensacola - ORD Chicago O'Hare Intl
PNSORD
Pensacola
Sun 9/20
3:26 pm-12:23 am
1 stop8h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 10/1
6:00 am-9:49 am
1 stop3h 49m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 12/12
5:50 pm-10:55 pm
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 12/17
8:00 am-12:05 pm
1 stop4h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 10/10
5:40 pm-10:33 pm
1 stop4h 53m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 3/10
6:00 am-11:56 am
1 stop5h 56m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 12/15
8:00 am-12:05 pm
1 stop4h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sun 12/13
6:00 am-10:29 am
1 stop4h 29m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
Showing 1-10 of 50 resultsSorted by cheapest first
Compare providers for flights from Pensacola to Chicago
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 Pensacola to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Pensacola-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pensacola-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pensacola-Chicago 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 Pensacola-Chicago 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 Pensacola to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pensacola with our price prediction graph.
PNS-CHI
PNS-MDW
PNS-RFD
PNS-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 Pensacola to Chicago
PNS-CHI
PNS-MDW
PNS-RFD
PNS-ORD
What is the cheapest month to book a flight from Pensacola to Chicago?
Currently, February is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $279). Flying from Pensacola to Chicago in July is currently the most expensive (average of $415). 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 PNS to CHI?
Find hourly flight availability from Pensacola 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 September 16, 2026.
When flying from Pensacola to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Pensacola to Chicago?
Airfare is below average for this route at the moment.
Pensacola to Chicago flights typically cost between $332 and $378 in November.The cheapest round-trip price found within the last 5 days was $224 on Southwest (Nov 14-Nov 17).
What’s the top layover airport for flights from Pensacola to Chicago?
Share of 1-stop round-trip flights from Pensacola to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Orlando (MCO) – chosen by Cheapflights users on 83% of 1-stop itineraries from Pensacola to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Pensacola to Chicago?
Average round-trip fare for 1-stop flights from Pensacola to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Nashville (BNA) is the most affordable 1-stop option, with an average round-trip price of $303.
What’s the fastest layover option from Pensacola to Chicago?
Shortest average travel time for 1-stop one-way flights from Pensacola to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Nashville (BNA) have the shortest average one-way travel time for 1-stop routes: 5h 10m.
Which airport typically offers the quickest layover for flights from Pensacola to Chicago?
Average layover duration for 1-stop one-way flights from Pensacola to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Nashville (BNA) offer the fastest connection on this route, with an average layover time of 1h 43m.
How far ahead should I book a flight from Pensacola to Chicago?
The price you pay for your flight from Pensacola to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 September 16, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Pensacola to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Pensacola 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
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Hammond
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Pensacola and Chicago flights
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Top 4 airlines flying from Pensacola to Chicago
Discover the top 4 airlines that operate flights from Pensacola 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 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$188 | Average$388 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$358 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$219 | Average$360 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$237 | Average$397 | FlexibilityNo cancel fee | On-time63% |