$111+ Cheap flights from Chicago (CHI) to Pensacola (PNS)
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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Jul 17 — Jul 241
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 70 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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Best
Last-minute
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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 June 17, 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 June 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/178:05 am
ORD
- PNS
1 stop29h 22m
Multiple Airlines
Mon 8/317:32 pm
PNS
- ORD
1 stop16h 53m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$248
This Travelocity deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 9/264:49 pm
ORD
- PNS
1 stop21h 29m
Frontier
Mon 10/56:59 pm
PNS
- ORD
1 stop15h 02m
Frontier
Deal found 6/16![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/1711:06 am
ORD
- PNS
1 stop6h 58m
Frontier
Mon 9/215:30 pm
PNS
- ORD
1 stop6h 25m
Frontier
Deal found 6/16![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/136:05 am
ORD
- PNS
1 stop6h 35m
Multiple Airlines
Tue 10/203:15 pm
PNS
- ORD
1 stop22h 01m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$263
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 9/264:49 pm
ORD
- PNS
1 stop21h 29m
Frontier
Sat 10/36:59 pm
PNS
- ORD
1 stop15h 02m
Frontier
Deal found 6/16![Frontier logo]()
$266
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/179:57 pm
ORD
- PNS
1 stop20h 51m
Frontier
Mon 8/315:30 pm
PNS
- ORD
1 stop5h 44m
Frontier
Deal found 6/16![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:05 am
ORD
- PNS
1 stop10h 47m
Multiple Airlines
Tue 8/49:15 am
PNS
- ORD
1 stop27h 00m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$272
This Orbitz deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:26 am
ORD
- PNS
1 stop7h 07m
Frontier
Mon 10/56:59 pm
PNS
- ORD
1 stop15h 02m
Frontier
Deal found 6/16![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/65:13 pm
ORD
- PNS
1 stop22h 17m
Multiple Airlines
Mon 8/107:32 pm
PNS
- ORD
1 stop16h 43m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$280
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/105:13 pm
ORD
- PNS
1 stop22h 33m
Frontier
Sat 8/157:26 pm
PNS
- ORD
1 stop27h 44m
Frontier
Deal found 6/16![Frontier logo]()
$281
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/315:13 pm
ORD
- PNS
1 stop25h 28m
Frontier
Tue 8/44:41 pm
PNS
- ORD
1 stop6h 29m
Frontier
Deal found 6/16![Frontier logo]()
$287
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/145:13 pm
ORD
- PNS
1 stop22h 21m
Frontier
Fri 7/174:11 pm
PNS
- ORD
1 stop6h 59m
Frontier
Deal found 6/16![Frontier logo]()
$288
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 June 17, 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 June 17, 2026.
This Delta deal was found by Cheapflights users on 6/12. 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 8/224:39 pm
MDW
- PNS
1 stop4h 58m
Delta
Wed 8/2611:51 am
PNS
- MDW
1 stop4h 24m
Delta
Deal found 6/12![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 6/12. 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.
Sat 9/196:50 am
MDW
- PNS
1 stop8h 05m
Southwest
Tue 9/224:20 pm
PNS
- MDW
1 stop6h 00m
Southwest
Deal found 6/12![Southwest logo]()
$365
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 10/1311:05 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Sat 10/174:18 pm
PNS
- ORD
Nonstop2h 42m
United Airlines
Deal found 6/12![United Airlines logo]()
$376
This KAYAK deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2011:59 am
ORD
- PNS
Nonstop2h 27m
American Airlines
Fri 7/243:15 pm
PNS
- ORD
Nonstop2h 47m
American Airlines
Deal found 6/16![American Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 6/12. 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 8/226:05 am
MDW
- PNS
1 stop4h 35m
Delta
Tue 8/256:00 am
PNS
- MDW
1 stop3h 59m
Delta
Deal found 6/12![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 10/222:45 pm
MDW
- PNS
1 stop7h 20m
Southwest
Tue 10/276:05 pm
PNS
- MDW
1 stop3h 45m
Southwest
Deal found 6/12![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/106:00 am
MDW
- PNS
1 stop6h 51m
Delta
Tue 10/137:00 am
PNS
- MDW
1 stop4h 56m
Delta
Deal found 6/16![Delta logo]()
$365
This United Airlines deal was found by Cheapflights users on 6/13. 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 9/110:40 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Wed 9/22:20 pm
PNS
- ORD
Nonstop2h 40m
United Airlines
Deal found 6/13![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sat 7/117:45 am
MDW
- PNS
2 stops7h 55m
Southwest
Tue 7/143:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 6/13![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 6/12. 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 8/1810:54 am
MDW
- PNS
1 stop4h 00m
Delta
Thu 8/276:08 pm
PNS
- MDW
1 stop4h 28m
Delta
Deal found 6/12![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 8/1810:40 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Wed 8/192:20 pm
PNS
- ORD
Nonstop2h 40m
United Airlines
Deal found 6/15![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 6/15. 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 8/16:00 am
MDW
- PNS
1 stop4h 46m
Delta
Sat 8/89:22 am
PNS
- MDW
1 stop6h 16m
Delta
Deal found 6/15![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 9/2610:45 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Mon 10/54:18 pm
PNS
- ORD
Nonstop2h 42m
United Airlines
Deal found 6/15![United Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 7/1710:38 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Sun 7/192:09 pm
PNS
- ORD
Nonstop2h 43m
United Airlines
Deal found 6/12![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:00 pm
MDW
- PNS
1 stop5h 51m
Delta
Tue 10/67:00 am
PNS
- MDW
1 stop4h 56m
Delta
Deal found 6/14![Delta logo]()
$406
This United Airlines deal was found by Cheapflights users on 6/13. 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 9/2510:45 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Sun 9/274:18 pm
PNS
- ORD
Nonstop2h 42m
United Airlines
Deal found 6/13![United Airlines logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/3010:38 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Sun 8/22:09 pm
PNS
- ORD
Nonstop2h 43m
United Airlines
Deal found 6/16![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 6/15. 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 8/15:30 am
ORD
- PNS
1 stop5h 16m
Delta
Sat 8/89:22 am
PNS
- ORD
1 stop5h 26m
Delta
Deal found 6/15![Delta logo]()
$456
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 7/184:05 pm
ORD
- PNS
1 stop5h 56m
United Airlines
Sun 7/192:09 pm
PNS
- ORD
Nonstop2h 43m
United Airlines
Deal found 6/12![United Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 9/2410:45 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Sun 9/277:00 am
PNS
- ORD
1 stop5h 25m
United Airlines
Deal found 6/13![United Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 6/13. 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 7/2210:38 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Wed 7/292:09 pm
PNS
- ORD
Nonstop2h 43m
United Airlines
Deal found 6/13![United Airlines logo]()
$475
Last-minute flights from Chicago to PensacolaDiscover last-minute flight deals from Chicago to Pensacola. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pensacola. Data last updated June 17, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:13 pm
ORD
- PNS
1 stop22h 21m
Frontier
Thu 7/94:11 pm
PNS
- ORD
1 stop6h 59m
Frontier
Deal found 6/17![Frontier logo]()
$283
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/75:13 pm
ORD
- PNS
1 stop22h 21m
Frontier
Sat 7/117:26 pm
PNS
- ORD
1 stop27h 44m
Frontier
Deal found 6/16![Frontier logo]()
$310
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:57 pm
ORD
- PNS
1 stop17h 39m
Frontier
Tue 7/144:41 pm
PNS
- ORD
1 stop6h 29m
Frontier
Deal found 6/17![Frontier logo]()
$300
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/145:13 pm
ORD
- PNS
1 stop22h 21m
Frontier
Fri 7/174:11 pm
PNS
- ORD
1 stop6h 59m
Frontier
Deal found 6/16![Frontier logo]()
$288
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:13 pm
ORD
- PNS
1 stop22h 01m
Frontier
Sun 7/194:11 pm
PNS
- ORD
1 stop6h 59m
Frontier
Deal found 6/17![Frontier logo]()
$306
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/179:57 pm
ORD
- PNS
1 stop17h 39m
Frontier
Fri 7/244:11 pm
PNS
- ORD
1 stop6h 59m
Frontier
Deal found 6/16![Frontier logo]()
$308
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 7/215:05 am
MDW
- PNS
1 stop6h 15m
Southwest
Sat 7/256:30 pm
PNS
- MDW
1 stop4h 50m
Southwest
Deal found 6/15![Southwest logo]()
$365
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/235:13 pm
ORD
- PNS
1 stop22h 01m
Frontier
Sun 7/264:11 pm
PNS
- ORD
1 stop17h 00m
Frontier
Deal found 6/16![Frontier logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:05 am
ORD
- PNS
1 stop29h 22m
Multiple Airlines
Sat 8/18:26 am
PNS
- ORD
1 stop14h 44m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$316
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/305:13 pm
ORD
- PNS
1 stop22h 01m
Frontier
Sun 8/24:11 pm
PNS
- ORD
1 stop6h 59m
Frontier
Deal found 6/16![Frontier logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:05 am
ORD
- PNS
1 stop10h 47m
Multiple Airlines
Tue 8/49:15 am
PNS
- ORD
1 stop27h 00m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$272
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/315:13 pm
ORD
- PNS
1 stop25h 28m
Frontier
Tue 8/44:41 pm
PNS
- ORD
1 stop6h 29m
Frontier
Deal found 6/16![Frontier logo]()
$287
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 June 17, 2026.
Search for one-way flight options from Chicago to Pensacola. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Mon 9/149:26 am
ORD
- PNS
1 stop27h 14m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Tue 9/85:30 pm
ORD
- PNS
1 stop19h 15m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Tue 8/115:13 pm
ORD
- PNS
1 stop18h 56m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/148:05 am
ORD
- PNS
1 stop23h 41m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$124
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:06 am
ORD
- PNS
1 stop6h 58m
Frontier
Deal found 6/17![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 6/15. 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.
Sat 7/189:57 pm
ORD
- PNS
1 stop20h 34m
Frontier
Deal found 6/15![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/117:45 am
ORD
- PNS
1 stop11h 00m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$135
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/159:57 pm
ORD
- PNS
1 stop20h 34m
Frontier
Deal found 6/16![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:05 am
ORD
- PNS
1 stop11h 41m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/205:30 pm
ORD
- PNS
1 stop23h 03m
Frontier
Deal found 6/16![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 9/1512:03 pm
MDW
- PNS
2 stops24h 42m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Mon 9/1412:03 pm
MDW
- PNS
2 stops24h 37m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$150
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $248 (Kiwi.com) |
One-way from | $111 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $437 |
Good round-trip deal | $396 or less |
Good one-way deal | $178 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 2,558,603 searches. Data last updated June 17, 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 - PNS
MDWPNS
Chicago Midway
Sat 8/22
4:39 pm-9:37 pm
1 stop4h 58m
Pensacola
Wed 8/26
11:51 am-4:15 pm
1 stop4h 24m
$365
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sat 9/19
6:50 am-2:55 pm
1 stop8h 05m
Pensacola
Tue 9/22
4:20 pm-10:20 pm
1 stop6h 00m
$365
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sat 8/22
6:05 am-10:40 am
1 stop4h 35m
Pensacola
Tue 8/25
6:00 am-9:59 am
1 stop3h 59m
$365
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sat 10/10
6:00 am-12:51 pm
1 stop6h 51m
Pensacola
Tue 10/13
7:00 am-11:56 am
1 stop4h 56m
$365
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 10/22
2:45 pm-10:05 pm
1 stop7h 20m
Pensacola
Tue 10/27
6:05 pm-9:50 pm
1 stop3h 45m
$366
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Tue 8/18
10:54 am-2:54 pm
1 stop4h 00m
Pensacola
Thu 8/27
6:08 pm-10:36 pm
1 stop4h 28m
$366
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sat 8/1
6:00 am-10:46 am
1 stop4h 46m
Pensacola
Sat 8/8
9:22 am-3:38 pm
1 stop6h 16m
$375
ChicagoPensacola
ORD - PNS
ORDPNS
Chicago O'Hare Intl
Tue 10/13
11:05 am-1:34 pm
Nonstop2h 29m
Pensacola
Sat 10/17
4:18 pm-7:00 pm
Nonstop2h 42m
$376
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sat 7/11
7:45 am-3:40 pm
2 stops7h 55m
Pensacola
Tue 7/14
3:45 pm-6:00 pm
Nonstop2h 15m
$391
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Fri 10/2
1:00 pm-6:51 pm
1 stop5h 51m
Pensacola
Tue 10/6
7:00 am-11:56 am
1 stop4h 56m
$406
Showing 1-10 of 42 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 June.
| 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
MDW-PNS
ORD-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
MDW-PNS
ORD-PNS
What is the cheapest month to book a flight from Chicago to Pensacola?
Currently, October is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $76). Flying from Chicago to Pensacola in March is currently the most expensive (average of $584). 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 June 17, 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 at noon could potentially save you up to 20% 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 June 17, 2026.
The most flights from CHI to PNS are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago to Pensacola?
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 68 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 June 17, 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
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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 locationsGulf Breeze
Foley
Navarre Beach
Navarre
Perdido Key
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Chicago and Pensacola flights
Browse other Chicago and Pensacola flight options. Last updated on June 17, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 17, 2026.
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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 2,558,603 searches. Data last updated June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$293 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$376 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$209 | Average$373 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$228 | Average$363 | FlexibilityNo cancel fee | On-time71% |