Benefits Manager Jobs in Chicago, IL
Benefits Manager jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, where major employers across healthcare, financial services, and professional services maintain large HR teams. Companies actively hiring include Arup, Grainger, and Highwire. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 27+ Benefits Manager jobs
SALARY
$140,627.46 - $152,158.92
POSITION SUMMARY
Serves as a total health and benefits expert for the CTA employee population. Oversees the activities and staff relating to employee benefits and wellbeing at the Authority including wellness education, financial literacy, health insurance, and other employee welfare initiatives and acting as an employee ombudsman regarding benefit and wellness related matters. Manages and is responsible for employee-wide health and wellness initiatives and seeks improvements and support of existing wellness programs. Oversees and participates in Requests for Proposals (RFP’s) from outside vendors for employee health services and programs.
Qualifications
PRIMARY RESPONSIBILITIES
- Outlines and oversees all aspects of the Employee Wellness program including both program design and administration.
o Leads the planning and delivery of the Wellness Program promoting employee healthy lifestyles, mental wellbeing and increased participation in the various Wellness Program initiatives.
o Manages the activities of the wellness program, its vendors, departmental managers, healthcare providers, and/or consultants as they pertain to delivering the Wellness programs.
o Focuses on strategic and targeted use of CTA’s Employee Assistance resources including all on-site EAP, post incident EAP, wellness coaches, and related trainings to ensure the wellbeing of employees is being met.
o Researches, designs, and creates new wellness initiatives tailored to meet Authority needs and encourages employees and their families to adopt healthy lifestyles.
o Uses relevant data to inform strategic wellness initiatives and partners with our vendors for a continuously evolving and impactful wellness program.
- Plans, implements, communicates, and oversees Authority’s benefit plans.
o Manages relationships with key health & welfare plan vendors ensuring cost effective and high-performance results.
o Oversees RFP's to ensure programs are competitive in the market, cost effective, and in compliance with Federal and State regulations.
o Prepares and communicates information to current and former employees about benefit programs, procedures, and changes.
o Sets short- and long-term goals for health benefit programs.
o Leads annual enrollment process including decisions related to plan offerings, design changes, and rates.
- Reviews and provides approval for the design, development, and implementation of communication strategies and marketing plans to provide Authority employees with a clear understanding of all CTA benefits and wellness programs and motivates increased participation in health initiatives.
- Ensures health plan designs meet needs of Authority and comply with the directions of management and negotiated labor contracts. Reviews initiatives to ensure all health & welfare benefits comply with appropriate legal requirements and reporting (Employee Retirement Income Security Act (ERISA); Health Insurance Portability and Accountability Act (HIPAA); Internal Revenue Service (IRS); Department of Labor (DOL); Affordable Care Act, etc.).
- Remains current with best practices to drive continuous improvement of employee health and decrease related employer costs on a year over year basis.
o Performs detailed analysis of Authority wellness information and data. Reports to senior management on metrics and trends on health and wellness related topics.
o Consults with other leadership/departments/functions within the Authority to align efforts and reinforce total population health goals.
o Gathers and analyzes data to measure success on internal and external wellness programs and initiatives.
o Compiles an annual comprehensive report that outlines the financial impact of benefit and wellness programs.
- Hires, trains, develops, monitors, and evaluates staff. Reviews and recommends personnel actions for approval.
- Performs related duties as assigned.
MANAGEMENT RESPONSIBILITIES
Reporting to this position are the following jobs:
Job Title
- Manager, Wellness
- Wellness Contractors
- Senior Benefits Administrators
- Senior Coordinator, Benefits
- Coordinator, Benefits
- Benefits Services Specialists
CHALLENGES
- Keeping abreast of federal, state, and local laws and regulations related to health and wellness programs to ensure Authority compliance.
- Designing and recommending enhancements to new and existing Wellness programs that remain cost effective and consistent with industry trends and corporate goals and objectives.
EDUCATION/EXPERIENCE REQUIREMENTS
- Bachelor’s degree in Human Resources, Business Administration, Marketing, Communications, Health Education (Clinical or Health Related Field such as Exercise, Nutrition, Nursing, or Public Health, Health Promotion, Exercise Science, Nutrition, Nursing, Corporate Wellness, or a related field, plus five (5) years of administration experience designing and implementing benefits and wellness programs, or an equivalent combination of education and experience relating to this position.
- Certified Benefits Professional, Certified Wellness Practitioner, and/or any additional related professional certification(s) preferred.
PHYSICAL REQUIREMENTS
- Requires remaining stationary for extended periods of time and constantly operating a computer and other office productivity machinery.
- Service Area Requirement: Exempt (Non-Union) employees must live within the boundaries of the CTA Statutory Service Area either at the time of employment or within 6 months of beginning employment at CTA.
KNOWLEDGE, SKILLS, AND ABILITIES
- Detailed knowledge of project management practices and techniques.
- Detailed knowledge of practices and methods in designing communication strategies and marketing plans, specifically related to benefits and wellness programs.
- Detailed knowledge of laws and regulations relating to health and wellness benefits.
- Detailed knowledge in the methods and practices in benefits design and administration.
- Working knowledge and understanding of human resources management to include current trends and human resources metrics.
- Working knowledge of Human Resources theories and principles.
- Working knowledge of the practices and methods of event planning and coordinating.
- General knowledge of various trade contracts and unions.
- Strong skills in data management, analysis and reporting.
- Strong analytical and problem-solving skills.
- Strong verbal, written communication and presentation skills.
- Strong organizational and prioritization skills.
- Intermediate software skills, including Word, Excel, PowerPoint, Internet and Oracle database.
- Ability to manage and motivate staff members to be successful.
- Ability to drive results by identifying and resolving significant problems within scope of responsibility.
WORKING CONDITIONS
- General office environment.
- This position is considered a "C-List" position under the “Revolving Door” prohibition within the State Officials and Employees Act (5 ILCS 430/5-45), which contains a number of post-employment restrictions CTA employees in C-list designated positions must follow. Among other requirements listed in this statute, CTA employees in C-list designated positions are required to follow State notification procedures to the Office of the Executive Inspector General prior to acceptance of any applicable non-State employment or may be fined significant penalties.
- Required to travel to various CTA remote locations throughout the Chicagoland area.
- Subject to normal garage and shop working conditions such as noise, dust, grease, moving vehicles, etc. when visiting field locations.
- Travels to various locations and exposed to prevailing weather conditions.
EQUIPMENT, TOOLS, AND MATERIALS UTILIZED
- Standard office equipment.
- Personal computer and related software (Microsoft Office Suite, Oracle, etc.).
Final salary will be determined in part by the qualifications of the selected candidate and may be higher or lower than target.
Applicants, if hired,must comply with CTA's residency ordinance.
CTA IS AN EQUAL OPPORTUNITY EMPLOYER
No employee or applicant for employment will be discriminated against because of race, color, creed, religion, sex, marital status, national origin, sexual orientation, ancestry, age, unfavorable military discharge, disability or any other status protected by federal, state, or local laws; except where a bona fide occupational qualification exists We are committed to providing an inclusive environment for our workforce and supporting the communities we serve. CTA will make reasonable accommodations for the known disabilities of otherwise qualified applicants for employment as well as its employees, unless undue hardship would result. If you require an accommodation in the application or hiring process, please contact arc@transitchicago.com prior to the submission of your application or upon notification of your actual test date. CTA will work with you to determine if an accommodation can be provided.
During the hiring process, CTA's Human Resources department will contact candidates with next steps . Failure to respond to these correspondences in a timely fashion may result in your application being closed out for non-responsiveness.
Please click link below to review the benefits offered at the CTA.
https://www.transitchicago.com/hrbenefits/
Primary Location
: USA-Illinois-ChicagoJob
: Human ResourcesJob Posting
: Oct 23, 2026, 3:07:22 PMSALARY
$140,627.46 - $152,158.92
POSITION SUMMARY
Serves as a total health and benefits expert for the CTA employee population. Oversees the activities and staff relating to employee benefits and wellbeing at the Authority including wellness education, financial literacy, health insurance, and other employee welfare initiatives and acting as an employee ombudsman regarding benefit and wellness related matters. Manages and is responsible for employee-wide health and wellness initiatives and seeks improvements and support of existing wellness programs. Oversees and participates in Requests for Proposals (RFP’s) from outside vendors for employee health services and programs.
Qualifications
PRIMARY RESPONSIBILITIES
- Outlines and oversees all aspects of the Employee Wellness program including both program design and administration.
o Leads the planning and delivery of the Wellness Program promoting employee healthy lifestyles, mental wellbeing and increased participation in the various Wellness Program initiatives.
o Manages the activities of the wellness program, its vendors, departmental managers, healthcare providers, and/or consultants as they pertain to delivering the Wellness programs.
o Focuses on strategic and targeted use of CTA’s Employee Assistance resources including all on-site EAP, post incident EAP, wellness coaches, and related trainings to ensure the wellbeing of employees is being met.
o Researches, designs, and creates new wellness initiatives tailored to meet Authority needs and encourages employees and their families to adopt healthy lifestyles.
o Uses relevant data to inform strategic wellness initiatives and partners with our vendors for a continuously evolving and impactful wellness program.
- Plans, implements, communicates, and oversees Authority’s benefit plans.
o Manages relationships with key health & welfare plan vendors ensuring cost effective and high-performance results.
o Oversees RFP's to ensure programs are competitive in the market, cost effective, and in compliance with Federal and State regulations.
o Prepares and communicates information to current and former employees about benefit programs, procedures, and changes.
o Sets short- and long-term goals for health benefit programs.
o Leads annual enrollment process including decisions related to plan offerings, design changes, and rates.
- Reviews and provides approval for the design, development, and implementation of communication strategies and marketing plans to provide Authority employees with a clear understanding of all CTA benefits and wellness programs and motivates increased participation in health initiatives.
- Ensures health plan designs meet needs of Authority and comply with the directions of management and negotiated labor contracts. Reviews initiatives to ensure all health & welfare benefits comply with appropriate legal requirements and reporting (Employee Retirement Income Security Act (ERISA); Health Insurance Portability and Accountability Act (HIPAA); Internal Revenue Service (IRS); Department of Labor (DOL); Affordable Care Act, etc.).
- Remains current with best practices to drive continuous improvement of employee health and decrease related employer costs on a year over year basis.
o Performs detailed analysis of Authority wellness information and data. Reports to senior management on metrics and trends on health and wellness related topics.
o Consults with other leadership/departments/functions within the Authority to align efforts and reinforce total population health goals.
o Gathers and analyzes data to measure success on internal and external wellness programs and initiatives.
o Compiles an annual comprehensive report that outlines the financial impact of benefit and wellness programs.
- Hires, trains, develops, monitors, and evaluates staff. Reviews and recommends personnel actions for approval.
- Performs related duties as assigned.
MANAGEMENT RESPONSIBILITIES
Reporting to this position are the following jobs:
Job Title
- Manager, Wellness
- Wellness Contractors
- Senior Benefits Administrators
- Senior Coordinator, Benefits
- Coordinator, Benefits
- Benefits Services Specialists
CHALLENGES
- Keeping abreast of federal, state, and local laws and regulations related to health and wellness programs to ensure Authority compliance.
- Designing and recommending enhancements to new and existing Wellness programs that remain cost effective and consistent with industry trends and corporate goals and objectives.
EDUCATION/EXPERIENCE REQUIREMENTS
- Bachelor’s degree in Human Resources, Business Administration, Marketing, Communications, Health Education (Clinical or Health Related Field such as Exercise, Nutrition, Nursing, or Public Health, Health Promotion, Exercise Science, Nutrition, Nursing, Corporate Wellness, or a related field, plus five (5) years of administration experience designing and implementing benefits and wellness programs, or an equivalent combination of education and experience relating to this position.
- Certified Benefits Professional, Certified Wellness Practitioner, and/or any additional related professional certification(s) preferred.
PHYSICAL REQUIREMENTS
- Requires remaining stationary for extended periods of time and constantly operating a computer and other office productivity machinery.
- Service Area Requirement: Exempt (Non-Union) employees must live within the boundaries of the CTA Statutory Service Area either at the time of employment or within 6 months of beginning employment at CTA.
KNOWLEDGE, SKILLS, AND ABILITIES
- Detailed knowledge of project management practices and techniques.
- Detailed knowledge of practices and methods in designing communication strategies and marketing plans, specifically related to benefits and wellness programs.
- Detailed knowledge of laws and regulations relating to health and wellness benefits.
- Detailed knowledge in the methods and practices in benefits design and administration.
- Working knowledge and understanding of human resources management to include current trends and human resources metrics.
- Working knowledge of Human Resources theories and principles.
- Working knowledge of the practices and methods of event planning and coordinating.
- General knowledge of various trade contracts and unions.
- Strong skills in data management, analysis and reporting.
- Strong analytical and problem-solving skills.
- Strong verbal, written communication and presentation skills.
- Strong organizational and prioritization skills.
- Intermediate software skills, including Word, Excel, PowerPoint, Internet and Oracle database.
- Ability to manage and motivate staff members to be successful.
- Ability to drive results by identifying and resolving significant problems within scope of responsibility.
WORKING CONDITIONS
- General office environment.
- This position is considered a "C-List" position under the “Revolving Door” prohibition within the State Officials and Employees Act (5 ILCS 430/5-45), which contains a number of post-employment restrictions CTA employees in C-list designated positions must follow. Among other requirements listed in this statute, CTA employees in C-list designated positions are required to follow State notification procedures to the Office of the Executive Inspector General prior to acceptance of any applicable non-State employment or may be fined significant penalties.
- Required to travel to various CTA remote locations throughout the Chicagoland area.
- Subject to normal garage and shop working conditions such as noise, dust, grease, moving vehicles, etc. when visiting field locations.
- Travels to various locations and exposed to prevailing weather conditions.
EQUIPMENT, TOOLS, AND MATERIALS UTILIZED
- Standard office equipment.
- Personal computer and related software (Microsoft Office Suite, Oracle, etc.).
Final salary will be determined in part by the qualifications of the selected candidate and may be higher or lower than target.
Applicants, if hired,must comply with CTA's residency ordinance.
CTA IS AN EQUAL OPPORTUNITY EMPLOYER
No employee or applicant for employment will be discriminated against because of race, color, creed, religion, sex, marital status, national origin, sexual orientation, ancestry, age, unfavorable military discharge, disability or any other status protected by federal, state, or local laws; except where a bona fide occupational qualification exists We are committed to providing an inclusive environment for our workforce and supporting the communities we serve. CTA will make reasonable accommodations for the known disabilities of otherwise qualified applicants for employment as well as its employees, unless undue hardship would result. If you require an accommodation in the application or hiring process, please contact arc@transitchicago.com prior to the submission of your application or upon notification of your actual test date. CTA will work with you to determine if an accommodation can be provided.
During the hiring process, CTA's Human Resources department will contact candidates with next steps . Failure to respond to these correspondences in a timely fashion may result in your application being closed out for non-responsiveness.
Please click link below to review the benefits offered at the CTA.
https://www.transitchicago.com/hrbenefits/
Primary Location
: USA-Illinois-ChicagoJob
: Human ResourcesJob Posting
: Oct 23, 2026, 3:07:22 PMSee All 27 Benefits Manager Jobs in Chicago
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Find Benefits Manager JobsBenefits Manager Job Market in Chicago
Who's Hiring
Top Industries Hiring
- Accounting & Auditing
- Healthcare & Medical Services
- Investment & Asset Management
- Consulting & Professional Services
Benefits Manager Jobs in Chicago: Frequently Asked Questions
How do I get a benefits manager job in Chicago?
Focus your search on Chicago's largest employment sectors: healthcare systems anchored on the Near North Side, financial services firms in the Loop, and the growing professional services companies in Fulton Market. Candidates with experience administering self-funded health plans, 401(k) administration, or leave management under Illinois law stand out locally. Certifications like CEBS or CBP sharpen your competitiveness, and connecting with Chicago SHRM chapter events helps you surface openings before they post publicly.
Which companies hire benefits managers in Chicago?
Companies currently hiring benefits managers in Chicago include Arup, Grainger, and Highwire, per current listings on Migrate Mate as of November 2026. Chicago's hiring mix skews heavily toward large hospital networks, insurance carriers headquartered downtown, and multinational corporations with Midwest regional offices that manage benefits across multi-state workforces.
Are there remote benefits manager jobs in Chicago?
Yes, though benefits manager roles lean more hybrid than fully remote, since vendor meetings, open enrollment events, and employee consultations often require in-person presence. About 63% of benefits manager openings tied to Chicago are remote or hybrid as of November 2026. The most remote-friendly work in Chicago tends to involve benefits analytics, carrier negotiations, and plan documentation rather than day-to-day employee-facing support.
How can I get a benefits manager job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving laterally from an HR generalist or HR coordinator role at a mid-size Chicago employer, where you can take ownership of open enrollment or leave administration. Chicago's large hospital networks and insurance companies also hire benefits specialists or benefits analysts as stepping-stone roles. Completing an HRCI or SHRM credential while in a junior role signals intent, and volunteering with Chicago SHRM helps build local professional connections that lead to referrals.
Which industries hire the most benefits managers in Chicago?
Chicago benefits manager roles concentrate in Accounting & Auditing, Healthcare & Medical Services, and Investment & Asset Management, based on current listings on Migrate Mate as of November 2026. Chicago's role as a hub for large hospital systems, global insurance carriers, and major corporate headquarters creates consistent, high-volume demand for professionals who can manage complex, multi-site benefit programs.
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