Investigator Jobs in Chicago, IL
Investigator jobs in Chicago are concentrated in the Loop, River North, and the Magnificent Mile corridor, with strong demand across financial services, insurance, healthcare, and corporate security. Employers hiring right now include Northwestern University, Professional Case Management, and Command Investigations. See the openings below and apply to the ones that match your experience.
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SUPERVISING INVESTIGATOR
Job Number: 419748
Description
JOB ANNOUNCEMENT
Supervising Investigator
Chicago Fire Department
Internal Affairs Division
Number of Positions: 1
(Additional vacancies possible pending budget approval)
Starting Salary: $85,548
Applications for this position will be accepted until 11:59pm CDT on 09/29/2026
Under supervision, supervises staff engaged in the investigation of cases involving allegations of criminal activity, official misconduct, and residency violations by City employees, including large-scale and complex investigations, and performs related duties as required.
ESSENTIAL DUTIES
- Reviews complaints and allegations and assigns cases to investigative staff
- Monitors cases assigned to staff, ensuring investigations are timely and in compliance with established procedures
- Reviews investigative reports prepared by staff for completeness of information and to assess findings and recommendations
- Coordinates large-scale investigations requiring coordination between departments and outside agencies
- Participates in and provides direction to staff investigating complex cases requiring specialized investigative and surveillance skills
- Assists in establishing operating procedures and work practices
- Monitors staff's use of surveillance equipment and conduct of covert investigations
- Meets with staff to review status of cases and evaluate work performance
- Trains and oversees the training of investigators on standard and specialized investigative practices and techniques
- Testifies in court, arbitrations, and Personnel Board hearings on investigations conducted and findings
- Prepares reports of completed investigations and staff performance for management review
- Confers with management and the Department of Law on legal issues relating to investigative activities
- Administers drug and alcohol tests to employees, as required
Additional duties may be required for this position
Location: Chicago Fire Department – Internal Affairs Division
3510 S. Michigan, Chicago, IL 60653 / Citywide
Days: Monday – Friday
Days Off: Saturday and Sunday
Hours: Hours may vary
THIS POSITION IS NOT IN CAREER SERVICE
Qualifications
MINIMUM QUALIFICATIONS
- Seven (7) years of work experience in the conduct of investigations of criminal or fraudulent activity OR seven (7) years of work experience in the performance of fact finding analyses and investigative research and reporting, OR
- Graduation from an accredited college with an Associate’s degree in the Social Sciences, Criminal Justice, Human Resources or a directly related field, plus five (5) years of work experience in the conduct of investigations of criminal or fraudulent activity OR five (5) years of work experience in the performance of fact finding analyses and investigative research and reporting, OR
- Graduation from an accredited college or university with a Bachelor's degree in the Social Sciences, Criminal Justice, Human Resources or a directly related field, plus three (3) years of work experience in the conduct of investigations of criminal or fraudulent activity OR three (3) years of work experience in the performance of fact finding analyses and investigative research and reporting, OR
- Graduation from an accredited college or university with a Master’s degree or higher in the Social Sciences, Criminal Justice, Human Resources or a directly related field, plus two (2) years of work experience in the conduct of investigations of criminal or fraudulent activity OR two (2) years of work experience in the performance of fact finding analyses and investigative research and reporting
Licensure, Certification, or Other Qualifications
- A valid State of Illinois driver's license is required
- Availability to work and duty watch is required
SELECTION REQUIREMENTS
This position requires applicants to complete an interview. The interviewed candidate(s) possessing the qualifications best suited to fulfill the responsibilities of the position, based on the interview will be selected.
The Chicago Fire Department may request that successful candidates pass a drug screen and background investigation. Persons offered employment must pass all pre-employment exams prior to appointment.
For Information on our employees benefits please visit our benefits website at: https://www.chicago.gov/city/en/depts/fin/benefits-office.html
For Information on our salary and title structure visit our classifications website at: City of Chicago :: Classification and Pay Plan
APPLICATION EVALUATION:
Initial evaluation will be based on information provided on the application and the documents submitted. Department of Human Resource staff will review applications after the final posting date. Staff will follow any and all required Employment/Hiring Plan provisions, federal, state and local laws, and Collective Bargaining Agreements when applicable. Staff will apply hiring preferences as required by the municipal code. Placement on an eligibility list is not an offer or guarantee of an interview nor employment with the City of Chicago.
COMMITMENT TO DIVERSITY:
To further our commitment to hiring applicants with diverse experience the City of Chicago has adopted the following ordinances 2-74-020 and 2-74-075. The ordinances provide a preference to applicants who meet minimum qualifications and who are veterans of the Armed Forces, and/or residents of Socio-Economically Disadvantaged Areas (SEDA) and/or Chicago Public School (CPS) high school graduates to be referred to departments for consideration. These hiring preferences do not apply to bidders, as Collective Bargaining Agreements define the hiring process for bidders. For positions covered by a collective bargaining agreement, bidders will be considered before external candidates. To learn more about our hiring practices click here.
ALL REFERENCES TO POLITICAL SPONSORSHIP OR RECOMMENDATION MUST BE OMITTED FROM ALL APPLICATION MATERIALS SUBMITTED FOR CITY EMPLOYMENT.
The City of Chicago is an Equal Employment Opportunity, Military Friendly, and Fair Chance Employer.
City of Chicago
Brandon Johnson, Mayor
Job Posting
: Sep 15, 2026, 10:40:57 AM
Closing Date (Period for Applying) - External
: Sep 29, 2026, 11:59:00 PM
BU: 10
Salary: $85,548
Pay Basis
: Yearly
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Who's Hiring



Top Industries Hiring
- Education
- Insurance
- Government & Public Sector
- Banking & Financial Services
Investigator Jobs in Chicago: Frequently Asked Questions
How do I get a investigator job in Chicago?
Focus your search on the Loop and River North, where the heaviest concentration of financial services firms, insurance carriers, and corporate legal departments hire investigators year-round. Healthcare systems on the Near North Side and logistics companies along the I-55 corridor also post regularly. Candidates with a background in fraud analysis, corporate compliance, or law enforcement transition well in this market, and familiarity with Illinois court records systems gives a practical edge.
Which companies hire investigators in Chicago?
Chicago investigator roles are posted by Northwestern University, Professional Case Management, and Command Investigations and others right now, based on current listings on Migrate Mate as of September 2026. The Chicago market skews toward large insurance carriers, financial institutions with internal audit teams, and managed care organizations that run active special investigations units.
Are there remote investigator jobs in Chicago?
Yes, though it depends heavily on the specialty: desk-based roles like fraud analysis, insurance claims review, and digital forensics support are commonly remote or hybrid, while field investigation and physical surveillance work is almost always on-site. About 36% of investigator openings tied to Chicago are remote or hybrid as of September 2026. Analytical and case-management functions within Chicago's large insurance and financial sectors are the roles most likely to offer flexible arrangements.
How can I get a investigator job in Chicago with little or no experience?
The most realistic entry path in Chicago is through insurance special investigations units, many of which hire claims associates or fraud analyst trainees with only a bachelor's degree and strong attention to detail. Chicago's large hospital networks and university medical centers also hire compliance assistants who move into investigation roles internally. Security analyst positions at Loop-based financial firms offer another lateral entry point. Volunteering with the Cook County public defender's office or a legal aid organization builds practical investigative exposure that Chicago employers notice.
Which industries hire the most investigators in Chicago?
The sectors hiring the most investigators in Chicago are Education, Insurance, and Government & Public Sector, based on current listings on Migrate Mate as of September 2026. Chicago's role as a national hub for insurance underwriting, commodities trading, and large healthcare networks drives sustained local demand across all three categories.
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