Nonstop flights from Pensacola to Chicago
2 airlines fly this route, with up to 2 flights a day.
PNSPensacola International
795 mi · 12 flights a week
ORDChicago O'Hare International
When they leave
Pensacola time2:20p2:59pFirst departure 2:20 PM, last 2:59 PM
Two in the afternoon, 2:20 PM to 2:59 PM.
Every flight
Earliest first
Schedules last checked Sep 20, 2026. Times are local.
Flying from Pensacola to Chicago
American Airlines flies most often, daily on the Embraer 175. United Airlines flies 5 times a week on the Boeing 737-800.
There are 1 or 2 flights every day of the week. The first arrival in Chicago is at 5:00 PM and the last at 5:49 PM. The flight covers 795 miles.
American Airlines is back on Nov 1.
Flying back, Chicago to Pensacola has 14 nonstop flights a week.
Return flights
More from Pensacola
Find the cheapest day to fly from Pensacola to Chicago.
Schedules as of Oct 9, 2026.