Generous Paid Time Off Jobs in Chicago, IL

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Looking for Generous Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Generous Paid Time Off position in the Chicago, IL area.

Armed Driver Guard

Company: Loomis Armored US, LLC

Location: Chicago, IL

Posted Jul 30, 2025

With a network of nearly 200 branches, Loomis armored transportation, cash management centers, and cash inventory vaults keep cash flowing throughout financial…

Powder Coat Painter

Company: PROMAN

Location: Chicago, IL

Posted Jul 30, 2025

Proficient in using various power tools related to the painting trade. Operate power tools and machinery safely and effectively during the painting process.

Fine Jewelry Sales and Project Management

Company: Christopher Duquet Fine Jewelry Design

Location: Evanston, IL

Posted Jul 30, 2025

Knowledge of social media platforms and digital marketing strategies. Work in a boutique environment where you can make a real impact on client relationships…

Registered Nurse / Educational Assistant

Company: LaGrange Area Department of Special Education

Location: Brookfield, IL

Posted Jul 30, 2025

A valid Illinois driver’s license and access to a reliable, insured vehicle *. All duties are performed in accordance with district/cooperative/state board of…

Now Hiring Grill Chefs

Company: Hawksmoor - Chicago

Location: Chicago, IL

Posted Jul 30, 2025

In this role, you’ll be responsible for working with and managing the charcoal grill to prepare high-quality, perfectly grilled meats, seafood, and vegetables…

Security Officers - Full Time - $22.15/hr

Company: Sunstates Security

Location: Northlake, IL

Posted Jul 30, 2025

The Security officer must read and become extremely knowledgeable of Post Orders and SOP and will be able to act quickly and efficiently according to such…

Service Technician Trainee Roofing

Company: Complete Bldg Maint Co

Location: Lombard, IL

Posted Jul 30, 2025

This entry-level position is ideal for individuals looking to develop their skills in the commercial roofing repair, and maintenance field.

Assistant Director, Event and Program Marketing

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

This position demands a blend of creativity, analytical skills, and project management expertise, with strong writing abilities to effectively promote topics…

Travel General Laborer Nights $18

Company: SPAR Inc.

Location: Chicago, IL

Posted Jul 30, 2025

Reliable transportation, valid driver’s license,. This role is made for road warriors — expect to be continuously on assignment outside your home state.

Assistant Director, Content

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

Minimum requirements include a college or university degree in related field. Bachelor’s degree in a writing-related field such as journalism, English, or…

UN Swing Driver

Company: Lakeshore Recycling Systems LLC

Location: Chicago, IL

Posted Jul 30, 2025

Must not have any license suspensions within the last 2 years. The Swing driver collects and hauls waste, recycling materials or containers to a disposal site…

Artificial Intelligence/Machine Learning (AI/ML) Engineer

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

Minimum requirements include a college or university degree in related field. Acts as a technical consultant and resource for faculty research, teaching, and/or…

Frequently Asked Questions

What are the typical salary ranges for Generous PTO roles by seniority?
Entry‑Level PTO Analyst: $55k–$70k; Mid‑Level PTO Manager: $80k–$110k; Senior PTO Director: $130k–$170k. These ranges vary by region and company size.
Which skills and certifications are required for Generous PTO positions?
Core skills: PTO policy design, HRIS configuration (Workday, SAP SuccessFactors), data analytics (SQL, Excel, Power BI), compliance knowledge (FERPA, GDPR). Certifications: SHRM‑CP/SHRM‑SCP, HRIS Certified Professional, Workday HCM Certification, SAP SuccessFactors HCM Certification.
Is remote work available for Generous PTO roles?
Approximately 70% of PTO analyst and benefits coordinator positions allow full‑time remote or hybrid work, especially in SaaS and tech firms. On‑site roles exist for compliance audit positions that require physical access to employee records.
What are the career progression paths in Generous PTO roles?
PTO Analyst → PTO Manager → PTO Director → HR Director / VP of People Experience → Chief People Officer. Each step expands strategic influence from policy design to workforce planning.
What are the current industry trends for Generous PTO?
AI‑driven leave analytics, continuous PTO policies, integration of mental‑health metrics, global time‑zone‑aware accrual systems, emphasis on employee well‑being dashboards. Companies are adopting flexible PTO models to attract and retain talent.

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