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.

Housekeeping Attendant

Company: East Bank Club

Location: Chicago, IL

Posted Aug 14, 2025

The Locker Room Housekeeping Attendant will help foster the culture of East Bank Club by maintaining a clean, organized, and fully stocked locker room while…

Project Manager

Company: Ryan Specialty

Location: Chicago, IL

Posted Aug 14, 2025

Identifies potential risks and develops mitigation strategies monitoring and managing risks throughout the project lifecycle.

Assistant Designer/ Sales Assistant

Company: Stone City Kitchen & Bath

Location: Chicago, IL

Posted Aug 14, 2025

We are looking for an Assistant to our Sales Associates to manage transactions, from design, budgeting and project managing. Must have strong follow-up skills.

Lamination Machine Operator - 2nd Shift w/ Shift Differential $$$

Company: PAXXUS

Location: Addison, IL

Posted Aug 14, 2025

Experience operating lamination equipment in a manufacturing facility. Ability to read user manuals and complete documentation in English.

Registered Nurse (RN)

Company: Northwestern Women's Health Associates

Location: Chicago, IL

Posted Aug 14, 2025

Current and valid RN license. Managing and triaging patient calls and electronic messages to prioritize care. This position is full-time, in-person.

Registered Nurse (RN)

Company: ALIYA on 87th

Location: Chicago, IL

Posted Aug 14, 2025

Active Registered Nurse (RN) license in the state of Illinois. Collaborate with allied health team members to develop and implement individualized care plans.

HVAC Master Technician/Technical Trainer

Company: Leslie Heating & Cooling

Location: Lombard, IL

Posted Aug 14, 2025

Provide field support and advanced troubleshooting for complex service or turnover calls. Run service calls (on demand). $85,000 – $125,000 per year*.

EXECUTIVE SOUS CHEF

Company: Culinaire

Location: Chicago, IL

Posted Aug 14, 2025

Recognized as the technical expert, teacher and trainer for this operation and the culinary team. Current and cutting edge on new products, presentations, and…

CDL A Flatbed Truck Driver - Home Weekly

Company: AWL Transport Inc. dba TLX

Location: Chicago, IL

Posted Aug 14, 2025

2 Years Verifiable Driving Experience w/ Steel coil & heavy haul experience. Must be 22 Years of Age. OUR FLATBED TRUCK DRIVERS EARN UP TO $80,000 PER YEAR –…

Office Administrator and Data Analyst

Company: E. J. Basler Company

Location: Schiller Park, IL

Posted Aug 14, 2025

Bachelor's degree in business, data analytics, or a related field. Perform regular data entry and data maintenance to ensure accuracy and consistency across…

Treatment Coordinator/Sale Consultant- Transform Lives with Smile

Company: Lakeshore Dental Studio

Location: Chicago, IL

Posted Aug 14, 2025

Celebrate wins—because helping someone say yes to a new smile feels amazing. Walk them through treatment options and payment plans. This is a *sales role*.

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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