Trainee Jobs in Chicago, IL
Trainee jobs in Chicago are concentrated across finance, healthcare, technology, and professional services, with openings spread through the Loop, River North, and the West Loop's growing corporate corridor. Employers actively hiring right now include CNA Insurance, State of Illinois, and Enterprise Mobility. Find a role that fits below and apply directly.
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You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.
JOB DESCRIPTION:
CNA’s Underwriting Trainee Program offers a rewarding career path for individuals interested in working for a company that provides hands-on experience and unique opportunities. As an Underwriting Trainee, you will have access to professional skills development, productivity courses and much more. Our curriculum provides:
- Instruction in insurance basics; underwriting, professional, sales and marketing skills.
- Technical training within discipline(s) and deeper knowledge of the broader industry.
- A combination of on-the-job and virtual training.
- Exposure to multiple lines of business and industry segments through a formal mentoring program.
- Instructor-led training, testing, self-study courses, Web-based training and practical application.
- A working relationship with critical enterprise-wide support functions.
We offer an opportunity for you to work with other underwriting, risk control and claim consultants to meet the evolving insurance needs of our clients. CNA’s underwriters are responsible for selecting and pricing risks that have profit potential. The process requires underwriters to evaluate a business by reviewing industry, business, and government data, then deciding whether to accept or decline the risk. The underwriter is also responsible for pricing, as well as maintaining a steady flow of new and renewal business. Our effective career pathing programs, including our leadership tracks, offer you the opportunity to grow your career at CNA. This position will work on a hybrid schedule from our offices in Chicago, IL.
Knowledge, Skills & Experience:
- Bachelor’s degree with a minimum 3.0 GPA strongly preferred; equivalent experience considered.
- Commitment to develop knowledge and understanding of underwriting.
- Strong sales aptitude.
- Effective analytical and problem-solving skills, good verbal and written communication skills, and the ability to learn rapidly.
- Excellent interpersonal skills, including the ability to influence, overcome obstacles, and develop positive business relationships.
#LI-MA1
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I n certain jurisdictions, CNA is legally required to include a reasonable estimate of the compensation for this role. In District of Columbia , California, Colorado, Connecticut, Illinois , Maryland , Massachusetts , New York and Washington, the national base pay range for this job level is $35,000 to $65,000 annually. Salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location. CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals. For a detailed look at CNA’s benefits, please visit cnabenefits.com .
CNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page .
CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact leaveadministration@cna.com
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Who's Hiring
- CNA Insurance26

- State of Illinois26

- Enterprise Mobility20

- ALDI7

- QUAD7

Trainee Jobs in Chicago: Frequently Asked Questions
How do I get a trainee job in Chicago?
The most direct path is targeting Chicago's dense concentration of financial services firms in the Loop, large health systems on the Near North Side, and technology companies anchored in the West Loop and River North. Employers there often prefer candidates with relevant coursework, a completed internship, or familiarity with industry-specific software. Applying directly through company career pages and following up promptly gives candidates a real edge in Chicago's competitive market.
Which companies hire trainees in Chicago?
Companies currently hiring trainees in Chicago include CNA Insurance, State of Illinois, and Enterprise Mobility, per current listings on Migrate Mate as of November 2026. Chicago's mix of global headquarters, regional bank branches, major hospital networks, and mid-size professional services firms means trainee openings appear across a wide range of employer sizes and sectors.
Are there remote trainee jobs in Chicago?
Yes, though availability depends heavily on the role: hands-on or clinical trainee positions are almost always on-site, while analytical, financial, and technology-focused trainee roles are more likely to offer flexibility. About 82% of trainee openings tied to Chicago are remote or hybrid as of November 2026, with the highest concentration of remote options in corporate training programs at the Loop's finance and consulting firms.
How can I get a trainee job in Chicago with little or no experience?
The most realistic entry path in Chicago is pursuing structured rotational trainee programs at the city's large employers in banking, insurance, and healthcare administration, many of which are designed specifically for candidates without prior professional experience. Chicago community colleges and universities also have established pipelines into local companies that prioritize recent graduates. Volunteering for Chicago-based nonprofit or civic organizations in a relevant function, then applying to those organizations' entry trainee openings, is another route that consistently produces results.
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