Generous Paid Time Off Jobs in Chicago, IL

73,229 open positions · Updated daily

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.

Affiliate Marketing Director- Legal/Motor Vehicle Accident Leads

Company: The Driscoll Firm, LLC

Location: Chicago, IL

Posted Jul 31, 2025

This is a rare opportunity to *build and own a direct affiliate channel* from the ground up—no middlemen, no third-party networks—just performance, transparency…

Substitute Teacher

Company: Swing Education

Location: Evanston, IL

Posted Jul 31, 2025

No early morning phone calls. $180-$240 per day depending on school, location, and certification. We support substitute teachers with helpful tools, optional…

Substitute Teacher

Company: Swing Education

Location: Chicago, IL

Posted Jul 31, 2025

No early morning phone calls. $180-$240 per day depending on school, location, and certification. We support substitute teachers with helpful tools, optional…

Customer Service Representative (CSR)

Company: Perillo Collision

Location: Chicago, IL

Posted Jul 31, 2025

Process repair orders, insurance claims, and payments, ensuring accuracy and compliance with procedures. Maintain accurate records of customer interactions and…

Streets & Utilities - Laborer

Company: Village of Lincolnwood

Location: Lincolnwood, IL

Posted Jul 31, 2025

Work involves performance of a variety of tasks which may include maintenance and repair of Village water and sewer lines.

Sous Chef

Company: Gibsons Italia

Location: Chicago, IL

Posted Jul 31, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

Part Time Custodian

Company: ServiceMaster Commercial Cleaning Solutions

Location: Chicago, IL

Posted Jul 31, 2025

Reliable Transportation and a valid Driver’s License. Clean all common space areas including kitchen, lobby and break rooms to ServiceMaster specifications.

Janitorial Support Team / Floater - Night

Company: Bee Line Support, Inc.

Location: Chicago, IL

Posted Jul 31, 2025

As Bee Line’s front-line cleaning defense, you will perform general cleaning duties, such as cleaning floors, vacuuming rugs, washing walls and glass, and…

Sous Chef

Company: Quartino Ristorante

Location: Chicago, IL

Posted Jul 31, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

Castline Operator - Machine Operator

Company: Intertape Polymer Group (IPG)

Location: Chicago, IL

Posted Jul 31, 2025

Maintains equipment through the completion of assigned preventative maintenance tasks and minor repair techniques as required. Ability to lift 50 pounds.

HVAC Technician

Company: Temperature Doctors Heating & Cooling, Inc

Location: Chicago, IL

Posted Jul 31, 2025

Valid driver’s license and clean driving record. Must have own hand tools (preferred). Perform diagnostics using schematics and technical documentation.

Custodian

Company: Facilities Performance Group, LLC

Location: Franklin Park, IL

Posted Jul 31, 2025

Adheres to established procedures to provide a safe working environment including complying with OSHA, state/local, federal, and company regulations.

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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