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.

CDL-A Truck Driver - 1099 - Up to $5,000 / week

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. No credit check, $0 down. Balloon payment at end of term. Earn 70% of line haul.

Marketing Director - Personal Injury experience

Company: Zentech Consulting

Location: Chicago, IL

Posted Aug 06, 2025

Identify and develop new business opportunities within the legal industry. Your ability to understand what drives consumer decisions and translate that into…

Associate Graphic Design

Company: AmTab Manufacturing

Location: Bensenville, IL

Posted Aug 06, 2025

As a minority-owned, 100% made-in-the-USA company, AmTab is proud to own our design, manufacturing, and installation process from start to finish.*.

Senior Manager, Software Engineering, Back End (Java, Node, AWS)

Company: Capital One

Location: Chicago, IL

Posted Aug 06, 2025

That includes everything from credit assessment and terms decisioning, to invoicing and payment processing, to servicing, collections and cash application.

Senior Industrial Hygiene Project Manager

Company: Specialty Consulting Inc.

Location: Chicago, IL

Posted Aug 06, 2025

This is a hands-on position with 50% of time spent in the field, where you will be conducting field inspections for hazardous materials and provide oversight…

CDL-A Truck Driver: Company or 1099

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. *Top drivers earn up to $90,000 per year*. No credit check, $0 down. Balloon payment at end of term.

HVAC Technician

Company: JLL

Location: Chicago, IL

Posted Aug 06, 2025

A stationary engineer license is a must. When assigned to install new/used equipment, must be able to operate appropriate construction tools and equipment.

IT Product Manager

Company: Charles Schwab

Location: Chicago, IL

Posted Aug 06, 2025

Familiarity with social media, web design, and advanced trading applications; proficient in Excel and PowerPoint. User acceptance testing prior to releases.

Senior Security Governance, Risk & Compliance (GRC) Analyst

Company: Boeing

Location: Chicago, IL

Posted Aug 06, 2025

This role focuses on configuration, administration, and ongoing support to ensure effective cybersecurity risk visibility and reporting striving for highest…

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted Aug 06, 2025

Collaborate with and across Agile teams to design, develop, test, implement, and support technical solutions in full-stack development tools and technologies.

Tool Room Machinist 1st shift)

Company: Klein Tools

Location: Elk Grove Village, IL

Posted Aug 06, 2025

Fits and assembles parts into complete assembly, using jigs, fixtures, surface plates, surface table, hand tools and power tools. Ability to weld is a plus.

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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