Earn point on your loyalty program!arrow arc left

Cheap flights from Pittsburgh (PIT) 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 Pittsburgh (PIT) to Chicago (CHI)

How to find the cheapest flight from Pittsburgh (PIT) 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 Pittsburgh (PIT) 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 Pittsburgh (PIT) 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 Pittsburgh to Chicago in September , October 2026

29 Sep - 10 Oct $ 534.00
PIT
Pittsburgh
JetBlue Airways
1 STOPS
CHI
Chicago
CHI
Chicago
JetBlue Airways
1 STOPS
PIT
Pittsburgh
Pick dates
30 Sep - 10 Oct $ 534.00
PIT
Pittsburgh
JetBlue Airways
1 STOPS
CHI
Chicago
CHI
Chicago
JetBlue Airways
1 STOPS
PIT
Pittsburgh
Pick dates
29 Sep - 06 Oct $ 553.00
PIT
Pittsburgh
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PIT
Pittsburgh
Pick dates

Last minute flights from Pittsburgh to Chicago

30 Sep - 30 Sep $ 547.00
PIT
Pittsburgh
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PIT
Pittsburgh
Pick dates
30 Sep - 30 Sep $ 547.00
PIT
Pittsburgh
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PIT
Pittsburgh
Pick dates
29 Sep - 30 Sep $ 553.00
PIT
Pittsburgh
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
PIT
Pittsburgh
Pick dates

One-way flights to Chicago from Pittsburgh

2:42 PM - 8:51 PM
Frontier Airlines
1 Stops
9h 17m
PIT - CHI
$ 211
Kiwi
Pick dates
8:56 AM - 8:56 AM
United Airlines
0 Stops
1h 49m
PIT - CHI
$ 270
Kiwi
Pick dates
7:00 AM - 7:00 AM
United Airlines
0 Stops
1h 43m
PIT - CHI
$ 274
Kiwi
Pick dates

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