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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Overview

Open roles158+
Top employerCNA Insurance
Work type82% Hybrid
Top credentialBachelor's degree
Companies hiring16

Showing 5 of 158+ Trainee jobs

Underwriting Trainee - National Accounts Casualty, Wholesale Excess
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New 6h ago
Underwriting Trainee - National Accounts Casualty, Wholesale Excess
CNA Insurance
Chicago, Illinois
Account Management
Customer Service
Sales
$35k - $65k/yr
Hybrid
5,001-10,000

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Underwriting Trainee, Ocean Marine
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Added 3d ago
Underwriting Trainee, Ocean Marine
CNA Insurance
Chicago, Illinois
Customer Success
Sales
Solutions Engineering & Architecture
$35k - $65k/yr
Hybrid
5,001-10,000

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Underwriting Trainee, International
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Added 3d ago
Underwriting Trainee, International
CNA Insurance
Chicago, Illinois
Customer Success
Sales
Solutions Engineering & Architecture
$35k - $65k/yr
Hybrid
5,001-10,000

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Social Services Career Trainee
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Added 3d ago
Social Services Career Trainee
State of Illinois
Chicago, Illinois
Allied Health
Healthcare Administration
Mental & Behavioral Health
Social Work & Counseling
$4,747 - $6,446/yr
Hybrid
10,000+

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Financial Institutions Examiner Trainee - Ump
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Added 3d ago
Financial Institutions Examiner Trainee - Ump
State of Illinois
Chicago, Illinois
IT Support
Project Management
Technical Program Management
Hybrid
Master's degree in business administration
10,000+

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See All 158+ Trainee Jobs in Chicago

Find roles in Chicago that match your experience and apply in just a few clicks.

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Trainee Job Market in Chicago

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.

See All 158+ Trainee Jobs in Chicago

Find roles in Chicago that match your experience and apply in just a few clicks.

Find Trainee Jobs