Comprehensive Benefits Package Jobs in Chicago, Illinois

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Looking for Comprehensive Benefits Package jobs in Chicago, Illinois? Browse our curated listings with transparent salary information to find the perfect Comprehensive Benefits Package position in the Chicago, Illinois area.

Teacher (Kindergarten)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 04, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

General Manager

Company: Machine Hospitality Group

Location: Chicago, IL

Posted Aug 04, 2025

Ensure that the bars comply with relevant state and federal guidelines. Handle all guest service issues in an immediate and professional manner.

Doorman

Company: Edgewater Beach Apartments

Location: Chicago, IL

Posted Aug 04, 2025

The Doorman is the first point of contact for residents, guests, visitors, and plays a crucial role in creating a welcoming and secure environment.

Low-Level C++ Software Engineer

Company: Wolverine Trading

Location: Chicago, IL

Posted Aug 04, 2025

Effective communication skills, with the ability to effectively engage both technical and non-technical stakeholders. Retirement Plans: 401K and Roth 401K.

Co-Teacher (Grade 3)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 04, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

Carpenter

Company: Yung Atelier

Location: Chicago, IL

Posted Aug 04, 2025

Reading and interpreting technical drawings and work orders. The ideal candidate has experience building frames for upholstered furniture, is detail-oriented,…

Accountant

Company: Cushman & Wakefield

Location: Chicago, IL

Posted Aug 04, 2025

May be assigned to either accounts payable or receivable and may handle billing/invoicing, cash receipts, data entry, budgets and budgeting, expenses, sales…

Maintenance Employee

Company: De LaSalle Institute

Location: Chicago, IL

Posted Aug 04, 2025

Resource room and faculty dining room.  Responsible for the cleanliness of offices, classrooms, executive office washrooms, faculty.

Teacher (Kindergarten)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 04, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

Frequently Asked Questions

What are the typical salary ranges by seniority for Comprehensive Benefits Package roles?
Entry‑level Benefits Analyst: $55,000–$70,000; Mid‑level Analyst/Manager: $70,000–$95,000; Senior Manager/Director: $95,000–$130,000; VP of Compensation & Benefits: $130,000–$170,000. Salaries shift 10–15% higher in major metros like San Francisco or New York and can dip 5–10% in smaller markets.
Which skills and certifications are most valuable for a career in Comprehensive Benefits Package?
Hands‑on expertise in Workday, SAP SuccessFactors, Gusto, or Zenefits; proficiency in Excel, SQL, and data‑visualization tools (Tableau, Power BI); deep knowledge of ACA, HIPAA, and ERISA regulations; and certifications such as CEBS (Certified Employee Benefits Specialist), CBP (Certified Benefits Professional), or SHRM‑CP/SCP. Demonstrating success in vendor negotiation and benefits analytics projects boosts employability.
Is remote work commonly available in Comprehensive Benefits Package positions?
Yes. 70–80% of Benefits Analyst and Manager roles offer fully remote or hybrid options, supported by cloud portals (e.g., Gusto Benefits Portal), video conferencing (Zoom, Teams), and collaboration platforms (Slack, SharePoint). Companies often set clear remote‑policy guidelines and require 2–3 in‑office days per month for onboarding or vendor meetings.
What does a typical career progression look like in this field?
Benefits Analyst → Senior Analyst → Benefits Manager → Senior Manager → Director of Compensation & Benefits → VP of Compensation & Benefits. Each step adds responsibilities for strategic planning, cross‑functional leadership, and executive reporting. Gaining a CEBS certification and leading a major benefits redesign project accelerates promotion.
What are the current industry trends shaping Comprehensive Benefits Package roles?
1) AI‑driven benefits analytics for predictive cost modeling; 2) Expansion of mental‑health and wellness programs (e.g., Calm, Headspace, Virgin Pulse); 3) Shift to flexible benefit baskets allowing employees to choose coverage; 4) Heightened focus on data privacy and GDPR/CCPA compliance; 5) Seamless integration of benefits modules within HRIS and payroll systems to reduce manual work.

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