Actuary Jobs in Chicago, IL
Actuary jobs in Chicago are concentrated in the Loop, River North, and the Magnificent Mile corridor, across insurance, consulting, and pension sectors. Demand is active year-round, with Milliman, AIG, and PwC among those currently posting roles. Scan the live roles below and apply to whichever ones fit.
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Description
As a Medical stop loss pricing actuarial lead, you will be a key member of the Financial Actuarial & Analytics (FAA) Community of Expertise. You will contribute to complex analytical work involving stop loss pricing and reserving as well as captive feasibility analysis. You will be responsible for translating that expertise into scalable intellectual capital used across FAA. You will partner with FAA practitioners, Client Service teams, Global Delivery Centers, and technology partners to develop, refine, and deploy reusable tools, models, and analytical frameworks. This role offers the opportunity to grow deep medical stop loss and captive expertise, financial acumen, and project management skills while working on high-impact, forward-looking initiatives alongside FAA leaders.
The Role:
- Lead the technical development of HealthMaps (Tillinghast), a cornerstone stop loss manual product used by many insurers and MGUs
- Work in close collaboration with product leader and customers to develop a common view of the business. Work in partnership with various stakeholders to identify emerging trends that should be incorporated into HealthMaps offerings.
- Lead projects across HealthMaps Team and in collaboration with our benefit teams
- Assist in captive feasibility analysis, captive business development activities, and captive annual pricing work
- Maintain stop loss benchmarking data, surveys, and provide proactive insights, identify the drivers and respond to clients’ inquiries
- Apply innovative approaches and leading-edge tools to analyze the business. Seek opportunities to leverage advanced analytics to provide greater insights. Ensure the quality of the data and its consistent application in the medical stop loss pricing and rate filings space.
- Assume an active leadership role and keep abreast of new medical stop loss trends and other external issues
Qualifications
- A minimum of 4+ years of experience in progressively complex actuarial roles. Knowledge and experience with medical stop loss pricing (preferred)
- Working towards or completed ASA, CAS or FSA credentials
- Leadership: Strength and experience as a teacher, manager, peer, leader and contributor to a positive culture
- Analytical and quantitative skills: theoretical foundation, work quality, productivity, creativity, ingenuity
- Software skills: Excel (expert), Word, PowerPoint; SQL (preferred), Power BI (preferred), database and programming skills, Snowflake knowledge (preferred), Python knowledge (preferred).
- Self-sufficient with competence to progress and build comprehensive pricing models and analytic solutions.
- Excellent verbal and written communication skills. Able to communicate complex technical concepts to a wide range of audiences including executive leadership and the board.
- Proven expertise leading and developing actuarial teams. This individual will have experience developing high performing teams with strong technical skills and business acumen.
- Experience presenting to executive management and external stakeholders.
- Demonstrated experience providing proactive guidance and sought-out insights to business leaders, executive management, and other stakeholders.
Compensation and Benefits
Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role and potential for revenue generation (Producer roles only).
Compensation
The base salary compensation range being offered for this role is $100,000.00 - $150, 000.00 USD annually.
This role is also eligible for an annual short-term incentive bonus.
Employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity.
This position will remain posted for a minimum of three business days from the date posted or until a sufficient/appropriate candidate slate has been identified
Company Benefits
WTW provides a competitive benefit package which includes the following (eligibility requirements apply):
- Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)
- Leave Benefits: Paid Holidays, Annual Paid Time Off (includes state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave), Paid Time Off (only included for Washington roles)
- Retirement Benefits: Qualified contributory pension plan (if eligible) and 401(k) plan with annual nonelective company contribution. Non-qualified retirement plans available to senior level colleagues who satisfy the plans’ eligibility requirements.
Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles County Fair Chance Ordinance for Employers, we will consider for employment qualified applicants with arrest and conviction records.
EOE, including disability/vets
See All 14 Actuary Jobs in Chicago
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Find Actuary JobsActuary Job Market in Chicago
Who's Hiring
- Milliman5

- AIG3

- PwC1

- WTW1

- Uber1

Top Industries Hiring
- Insurance11
- Consulting & Professional Services7
- Accounting & Auditing1
- Technology & Software1
- Investment & Asset Management1
Actuary Jobs in Chicago: Frequently Asked Questions
How do I get a actuary job in Chicago?
Focus your search on the Loop and River North, where the largest insurance carriers, benefits consulting firms, and pension fund managers are headquartered. Chicago's market rewards candidates who have passed at least two actuarial exams, with employers in health, property and casualty, and life insurance hiring most actively. Highlighting experience with predictive modeling or regulatory compliance work gives you a real edge with local firms.
Which companies hire actuarys in Chicago?
Chicago actuary roles are posted by Milliman, AIG, and PwC and others right now, based on current listings on Migrate Mate as of June 2026. Chicago's mix of global insurance carriers, regional mutual companies, and independent actuarial consulting boutiques keeps the employer base broad and consistently active.
Are there remote actuary jobs in Chicago?
Yes, though availability depends on the specialty. Actuarial analysis and modeling work is more remote-compatible than roles requiring regular client meetings or regulatory filings. About 30% of actuary openings tied to Chicago are remote or hybrid as of June 2026, with fully remote roles most common in health and life pricing work at larger carriers.
How can I get a actuary job in Chicago with little or no experience?
The most realistic entry path in Chicago is through internship programs at large insurance carriers headquartered in the Loop, where rotational programs actively recruit exam-sitting candidates. Entry-level actuarial analyst and junior pricing analyst roles at regional health plans and benefits consulting firms are also accessible. Passing even one or two Society of Actuaries or CAS exams before applying makes a significant difference in landing interviews with Chicago employers.
Which industries hire the most actuarys in Chicago?
The sectors hiring the most actuarys in Chicago are Insurance, Consulting & Professional Services, and Accounting & Auditing, based on current listings on Migrate Mate as of June 2026. Chicago's status as a national hub for insurance and financial services, combined with a strong concentration of corporate headquarters, keeps actuarial demand consistently high across those sectors.
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