Commercial Pilot Careers in Illinois: Where Chicago Pilots Can Work

Marko S.
Nov 17, 2025
2 min read

If you’re training at a flight school in Chicago and planning to turn flying into a career, earning a Commercial Pilot License (CPL) is your biggest milestone. With a CPL, you can legally get paid to fly — and there are more opportunities in Illinois than you might think.

Here’s a complete look at commercial pilot career paths in the Chicago aviation market.

What Can You Do With a Commercial Pilot License in Chicago?

Once you hold a CPL, real aviation jobs become available:

✔ Charter Pilot — business & private flights

✔ Flight Instructor (CFI) — build hours while teaching

✔ Aerial Survey Pilot — mapping & utility inspections

✔ Cargo / Mail Pilot — regional freight & logistics

✔ Banner Towing — advertising over Chicago beaches

✔ Pipeline & Powerline Patrol

✔ Sightseeing & Tourism Flights

Many Chicago-based commercial pilots start with instruction + survey flying to build hours.

CPL Requirements in Illinois

You must already have your Private Pilot License. Then complete:

Requirement	CPL Minimums
Total Flight Time	250 hours
Ground & Flight Instruction	Required
Written Exam	Pass FAA knowledge test
Practical Test	Pass checkride

Most students progress faster with multi-engine and instrument training.

Commercial Pilot Salary in Chicago

Starting salaries vary by role:

Career Path	Typical Starting Pay
CFI (Chicago region)	$25,000–$55,000
Charter Pilot	$40,000–$80,000
Cargo Pilot	$60,000–$110,000
Regional Airline FO	$55,000–$100,000+
Major Airline	$180,000–$400,000+ with seniority