$94+ Cheap flights from Pensacola (PNS) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Apr 14 — Apr 211
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 November or February, booked 37 days in advance, depart on a Thursday or Friday 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 March 15, 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 March 15, 2026.
This Frontier deal was found by Cheapflights users on 3/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:25 pm
PNS
- MDW
1 stop16h 34m
Frontier
Sun 4/199:04 am
MDW
- PNS
1 stop24h 13m
Frontier
Deal found 3/11![Frontier logo]()
$183
This Priceline deal was found by Cheapflights users on 3/13. 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.
Wed 4/82:15 pm
PNS
- ORD
1 stop5h 36m
Spirit Airlines
Sat 4/1112:45 pm
ORD
- PNS
1 stop8h 29m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Thu 5/71:42 pm
PNS
- ORD
1 stop9h 31m
Multiple Airlines
Tue 5/123:55 pm
ORD
- PNS
1 stop6h 34m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:31 pm
PNS
- ORD
1 stop6h 36m
Spirit Airlines
Mon 5/1810:50 am
ORD
- PNS
1 stop11h 39m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$203
This Frontier deal was found by Cheapflights users on 3/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:24 pm
PNS
- ORD
1 stop14h 26m
Frontier
Sun 4/194:57 pm
ORD
- PNS
1 stop16h 20m
Frontier
Deal found 3/11![Frontier logo]()
$204
This Cheapflightsfares deal was found by Cheapflights users on 3/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:15 pm
PNS
- ORD
1 stop5h 36m
Spirit Airlines
Sun 4/125:05 am
ORD
- PNS
1 stop8h 11m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 5/71:42 pm
PNS
- ORD
1 stop9h 31m
Multiple Airlines
Sun 5/105:05 am
ORD
- PNS
1 stop13h 53m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/186:36 am
PNS
- MDW
2 stops12h 01m
Multiple Airlines
Mon 4/279:14 am
MDW
- PNS
1 stop12h 24m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 5/26:36 am
PNS
- ORD
1 stop16h 31m
Multiple Airlines
Tue 5/53:55 pm
ORD
- PNS
1 stop6h 34m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Wed 4/87:00 am
PNS
- ORD
1 stop16h 36m
Multiple Airlines
Wed 4/156:08 pm
ORD
- PNS
2 stops21h 28m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:18 pm
PNS
- ORD
1 stop12h 18m
Spirit Airlines
Tue 4/2810:31 am
ORD
- PNS
1 stop11h 07m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 3/10. 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.
Sat 5/22:50 pm
PNS
- MDW
Nonstop2h 20m
Southwest
Sun 5/108:25 am
MDW
- PNS
Nonstop2h 15m
Southwest
Deal found 3/10![Southwest logo]()
$227
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 March 15, 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 March 15, 2026.
This Southwest deal was found by Cheapflights users on 3/10. 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.
Sat 5/22:50 pm
PNS
- MDW
Nonstop2h 20m
Southwest
Sun 5/108:25 am
MDW
- PNS
Nonstop2h 15m
Southwest
Deal found 3/10![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 3/12. 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 6/42:04 pm
PNS
- ORD
Nonstop2h 43m
United Airlines
Mon 6/810:33 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Deal found 3/12![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 3/10. 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 7/111:59 pm
PNS
- ORD
1 stop6h 19m
Delta
Fri 7/173:35 pm
ORD
- PNS
1 stop6h 27m
Delta
Deal found 3/10![Delta logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Fri 5/226:36 am
PNS
- RFD
1 stop12h 37m
Multiple Airlines
Sun 5/2411:27 am
RFD
- PNS
1 stop7h 31m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 3/10. 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 5/13:00 pm
PNS
- MDW
1 stop5h 30m
Southwest
Sun 5/38:25 am
MDW
- PNS
Nonstop2h 15m
Southwest
Deal found 3/10![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 5/53:00 pm
PNS
- ORD
1 stop5h 16m
Delta
Sat 5/166:05 pm
ORD
- PNS
1 stop5h 11m
Delta
Deal found 3/10![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 3/10. 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.
Sat 7/112:09 pm
PNS
- ORD
Nonstop2h 43m
United Airlines
Fri 7/1710:38 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Deal found 3/10![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 3/10. 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.
Sat 5/22:50 pm
PNS
- MDW
Nonstop2h 20m
Southwest
Mon 5/115:30 am
MDW
- PNS
1 stop7h 10m
Southwest
Deal found 3/10![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 3/14. 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.
Thu 5/76:00 am
PNS
- MDW
1 stop4h 00m
Delta
Mon 5/116:23 am
MDW
- PNS
1 stop4h 16m
Delta
Deal found 3/14![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 5/295:20 pm
PNS
- MDW
1 stop6h 10m
Southwest
Sun 6/75:00 am
MDW
- PNS
1 stop5h 00m
Southwest
Deal found 3/13![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 3/13. 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.
Tue 7/71:59 pm
PNS
- ORD
1 stop6h 19m
Delta
Fri 7/101:15 pm
ORD
- PNS
1 stop4h 47m
Delta
Deal found 3/13![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 5/295:20 pm
PNS
- MDW
1 stop6h 10m
Southwest
Tue 6/211:35 am
MDW
- PNS
2 stops8h 45m
Southwest
Deal found 3/13![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 3/15. 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.
Mon 7/67:15 pm
PNS
- ORD
1 stop4h 40m
Delta
Sat 7/115:55 pm
ORD
- PNS
1 stop4h 54m
Delta
Deal found 3/15![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 3/12. 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 5/145:56 pm
PNS
- ORD
Nonstop2h 54m
United Airlines
Mon 5/1810:40 am
ORD
- PNS
Nonstop2h 29m
United Airlines
Deal found 3/12![United Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 3/10. 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.
Thu 6/410:50 am
PNS
- MDW
2 stops6h 00m
Southwest
Mon 6/85:05 pm
MDW
- PNS
1 stop3h 35m
Southwest
Deal found 3/10![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 3/10. 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 4/102:05 pm
PNS
- MDW
1 stop9h 50m
Southwest
Mon 4/137:20 am
MDW
- PNS
1 stop5h 20m
Southwest
Deal found 3/10![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 3/10. 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.
Sat 4/188:00 am
PNS
- MDW
2 stops6h 35m
Southwest
Mon 4/278:00 am
MDW
- PNS
2 stops7h 40m
Southwest
Deal found 3/10![Southwest logo]()
$278
This United Airlines deal was found by Cheapflights users on 3/10. 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 4/107:00 am
PNS
- ORD
Nonstop2h 42m
United Airlines
Mon 4/1310:50 am
ORD
- PNS
Nonstop2h 28m
United Airlines
Deal found 3/10![United Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 3/10. 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 4/166:15 am
PNS
- ORD
1 stop8h 30m
United Airlines
Sun 4/196:10 pm
ORD
- PNS
Nonstop2h 28m
United Airlines
Deal found 3/10![United Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 3/10. 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.
Thu 6/47:50 am
PNS
- ORD
1 stop5h 40m
Southwest
Mon 6/87:20 pm
ORD
- PNS
2 stops14h 15m
Southwest
Deal found 3/10![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 3/11. 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.
Thu 5/285:35 am
PNS
- ORD
2 stops9h 55m
Southwest
Sun 5/316:00 am
ORD
- PNS
2 stops14h 30m
Southwest
Deal found 3/11![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 3/12. 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.
Fri 5/225:35 am
PNS
- ORD
2 stops9h 55m
Southwest
Sun 5/246:00 am
ORD
- PNS
2 stops12h 10m
Southwest
Deal found 3/12![Southwest logo]()
$453
Last-minute flights from Pensacola to ChicagoDiscover last-minute flight deals from Pensacola to Chicago. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Chicago. Data last updated March 15, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/182:15 pm
PNS
- ORD
1 stop9h 02m
Spirit Airlines
Wed 3/259:30 am
ORD
- PNS
1 stop11h 44m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$198
This Priceline deal was found by Cheapflights users on 3/13. 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.
Wed 4/82:15 pm
PNS
- ORD
1 stop5h 36m
Spirit Airlines
Sat 4/1112:45 pm
ORD
- PNS
1 stop8h 29m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Wed 4/87:00 am
PNS
- ORD
1 stop16h 36m
Multiple Airlines
Wed 4/156:08 pm
ORD
- PNS
2 stops21h 28m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$222
This Expedia deal was found by Cheapflights users on 3/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:36 pm
PNS
- ORD
1 stop8h 00m
Multiple Airlines
Fri 4/176:40 am
ORD
- PNS
1 stop8h 56m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 3/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:15 pm
PNS
- ORD
1 stop5h 36m
Spirit Airlines
Sun 4/125:05 am
ORD
- PNS
1 stop8h 11m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$208
This Frontier deal was found by Cheapflights users on 3/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:25 pm
PNS
- MDW
1 stop16h 34m
Frontier
Sun 4/199:04 am
MDW
- PNS
1 stop24h 13m
Frontier
Deal found 3/11![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 3/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:24 pm
PNS
- ORD
1 stop14h 26m
Frontier
Sun 4/194:57 pm
ORD
- PNS
1 stop16h 20m
Frontier
Deal found 3/11![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Fri 4/173:20 pm
PNS
- MDW
2 stops27h 17m
Multiple Airlines
Sun 4/199:04 am
MDW
- PNS
1 stop6h 32m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$213
This Expedia deal was found by Cheapflights users on 3/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:18 pm
PNS
- ORD
1 stop12h 18m
Spirit Airlines
Sun 4/1910:31 am
ORD
- PNS
1 stop5h 05m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Fri 4/173:20 pm
PNS
- ORD
1 stop7h 47m
Multiple Airlines
Wed 4/2211:07 am
ORD
- PNS
2 stops21h 48m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/186:36 am
PNS
- MDW
2 stops12h 01m
Multiple Airlines
Mon 4/279:14 am
MDW
- PNS
1 stop12h 24m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$215
This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:18 pm
PNS
- ORD
1 stop12h 18m
Spirit Airlines
Tue 4/2810:31 am
ORD
- PNS
1 stop11h 07m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$223
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 March 15, 2026.
Search for one-way flight options from Pensacola to Chicago. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
This Trip.com deal was found by Cheapflights users on 3/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:36 am
PNS
- MDW
1 stop9h 37m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$94
This Priceline deal was found by Cheapflights users on 3/15. 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 5/141:42 pm
PNS
- ORD
1 stop9h 31m
Frontier
Deal found 3/15![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 3/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/171:42 pm
PNS
- ORD
1 stop9h 31m
Frontier
Deal found 3/12![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Sat 5/26:36 am
PNS
- MDW
1 stop9h 37m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Sat 5/166:36 am
PNS
- ORD
1 stop16h 37m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 5/136:36 am
PNS
- ORD
1 stop16h 37m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/156:36 am
PNS
- MDW
1 stop25h 28m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:18 pm
PNS
- ORD
1 stop12h 18m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 3/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:36 pm
PNS
- ORD
1 stop25h 01m
Frontier
Deal found 3/12![Frontier logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/252:15 pm
PNS
- ORD
1 stop9h 02m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$106
This Super.com deal was found by Cheapflights users on 3/11. 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.
Sun 3/227:00 am
PNS
- ORD
1 stop9h 56m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:18 pm
PNS
- ORD
1 stop12h 18m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$111
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 March 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $183 (Frontier) |
One-way from | $94 (Trip.com) |
Popular in | March |
Cheapest in | November |
Average price | $352 |
Good round-trip deal | $282 or less |
Good one-way deal | $158 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 2,558,603 searches. Data last updated March 15, 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
Quickest round-trip
PensacolaChicago
PNS - MDW
PNSMDW
Pensacola
Sat 5/2
2:50 pm-5:10 pm
Nonstop2h 20m
Chicago Midway
Sun 5/10
8:25 am-10:40 am
Nonstop2h 15m
$227
PensacolaChicago
PNS - ORD
PNSORD
Pensacola
Thu 6/4
2:04 pm-4:47 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 6/8
10:33 am-1:02 pm
Nonstop2h 29m
$247
PensacolaChicago
PNS - MDW
PNSMDW
Pensacola
Fri 5/1
3:00 pm-8:30 pm
1 stop5h 30m
Chicago Midway
Sun 5/3
8:25 am-10:40 am
Nonstop2h 15m
$257
PensacolaChicago
PNS - MDW
PNSMDW
Pensacola
Sat 5/2
2:50 pm-5:10 pm
Nonstop2h 20m
Chicago Midway
Mon 5/11
5:30 am-12:40 pm
1 stop7h 10m
$257
PensacolaChicago
PNS - ORD
PNSORD
Pensacola
Sat 7/11
1:59 pm-8:18 pm
1 stop6h 19m
Chicago O'Hare Intl
Fri 7/17
3:35 pm-10:02 pm
1 stop6h 27m
$267
PensacolaChicago
PNS - ORD
PNSORD
Pensacola
Tue 5/5
3:00 pm-8:16 pm
1 stop5h 16m
Chicago O'Hare Intl
Sat 5/16
6:05 pm-11:16 pm
1 stop5h 11m
$267
PensacolaChicago
PNS - ORD
PNSORD
Pensacola
Sat 7/11
2:09 pm-4:52 pm
Nonstop2h 43m
Chicago O'Hare Intl
Fri 7/17
10:38 am-1:07 pm
Nonstop2h 29m
$267
PensacolaChicago
PNS - MDW
PNSMDW
Pensacola
Fri 5/29
5:20 pm-11:30 pm
1 stop6h 10m
Chicago Midway
Sun 6/7
5:00 am-10:00 am
1 stop5h 00m
$267
PensacolaChicago
PNS - MDW
PNSMDW
Pensacola
Fri 5/29
5:20 pm-11:30 pm
1 stop6h 10m
Chicago Midway
Tue 6/2
11:35 am-8:20 pm
2 stops8h 45m
$272
PensacolaChicago
PNS - MDW
PNSMDW
Pensacola
Thu 6/4
10:50 am-4:50 pm
2 stops6h 00m
Chicago Midway
Mon 6/8
5:05 pm-8:40 pm
1 stop3h 35m
$272
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 March.
| 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*2 stars |
- 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-ORD
PNS-RFD
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-ORD
PNS-RFD
How far ahead should I book a flight from Pensacola to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Pensacola to Chicago. Price data was last updated on March 13, 2026.
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 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Pensacola to Chicago?
Currently, June is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $118). Flying from Pensacola to Chicago in December is currently the most expensive (average of $229). 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 March 15, 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.
Weekly flight availability from Pensacola to Chicago
Explore weekly flight availability from Pensacola to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 15, 2026.
The most flights from PNS to CHI are scheduled on a Friday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Pensacola to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated March 15, 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.
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
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 locationsLansing
Merrillville
Hammond
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Benton Harbor
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Other flights to Chicago
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Pensacola and Chicago flights
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Other flights from Pensacola
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Top 5 airlines flying from Pensacola to Chicago
Discover the top 5 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 2,558,603 searches. Data last updated March 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$161 | Average$213 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$196 | Average$296 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$298 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$322 | FlexibilityNo cancel fee | On-time63% |