Earn point on your loyalty program!arrow arc left

Cheap flights from Pensacola (PNS) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)

How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Pensacola to Chicago in November , December 2026

18 Nov - 08 Dec $ 369.00
PNS
Pensacola
BREEZE
1 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
1 STOPS
PNS
Pensacola
Pick dates
18 Nov - 15 Dec $ 369.00
PNS
Pensacola
BREEZE
1 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
1 STOPS
PNS
Pensacola
Pick dates
18 Nov - 09 Dec $ 369.00
PNS
Pensacola
BREEZE
1 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
1 STOPS
PNS
Pensacola
Pick dates

Last minute flights from Pensacola to Chicago

23 Nov - 01 Dec $ 479.00
PNS
Pensacola
BREEZE
1 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
1 STOPS
PNS
Pensacola
Pick dates
18 Nov - 01 Dec $ 496.00
PNS
Pensacola
BREEZE
1 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
1 STOPS
PNS
Pensacola
Pick dates
17 Nov - 01 Dec $ 508.00
PNS
Pensacola
BREEZE
1 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
1 STOPS
PNS
Pensacola
Pick dates

One-way flights to Chicago from Pensacola

8:58 AM - 2:52 PM
Frontier Airlines
1 Stops
8h 9m
PNS - CHI
$ 231
Kiwi
Pick dates
8:48 AM - 2:52 PM
Frontier Airlines
1 Stops
8h 19m
PNS - CHI
$ 243
Kiwi
Pick dates
8:18 AM - 1:41 PM
Frontier Airlines
1 Stops
7h 34m
PNS - CHI
$ 261
Kiwi
Pick dates

How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.