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.

HVAC Technician (2 local locations)

Company: Lakeshore Sport & Fitness

Location: Chicago, IL

Posted Jul 10, 2025

Willing to use personal basic tools (specialty tools will be provided). Specific knowledge of mechanical, electrical and plumbing systems is also required.

Residential HVAC Installer

Company: Sanchez HVAC Services Inc.

Location: Stickney, IL

Posted Jul 10, 2025

Valid driver’s license and clean driving record. Communicate clearly with customers and answer basic questions about system use and care.

Project Manager

Company: Sidley Austin LLP

Location: Chicago, IL

Posted Jul 11, 2025

Demonstrated knowledge and execution of project management practices, tools and methodologies, including an appropriate project management tool (Smartsheet,…

Senior Accountant

Company: Alzheimer's Association

Location: Chicago, IL

Posted Jul 10, 2025

Assist with the entry of annual Budgets. Thorough understanding of developing and working with Excel spreadsheets. Full time or Part time: Full Time.

Maintenance Employee 2nd shift

Company: Fenwick High School

Location: Oak Park, IL

Posted Jul 10, 2025

Kitchen inspections and pest control. Dusting of furniture, equipment, partitions, classroom desks and offices. Cleaning and disinfecting bus fleet.

Manager of Grants Accounting

Company: BEDS Plus, Inc.

Location: La Grange, IL

Posted Jul 10, 2025

Build in system of double checks and internal audits for grant billing and submissions. Update accounting system and all relevant trackers for grant billing and…

IBP Project Manager

Company: The LaSalle Network

Location: Chicago, IL

Posted Jul 10, 2025

Translate business needs into functional specifications and oversee technical configuration. Be the driver of integrated planning excellence-apply today to help…

RETAIL SALES ASSOCIATE

Company: Ashley

Location: Niles, IL

Posted Jul 10, 2025

Maintain a welcoming, professional, visible presence at the front desk; engage with guests, ensuring they are always treated in a cordial, respectful manner…

Customer Service Agent - Full Time

Company: MedSpeed

Location: Elmhurst, IL

Posted Jul 11, 2025

Handle a large number of calls daily without losing enthusiastic voice and attitude, answering all calls promptly and efficiently.

Security Officer (unarmed)

Company: 900 Services, LLC-The Shops at 900

Location: Chicago, IL

Posted Jul 10, 2025

Provide exceptional customer service—greeting guests, assisting with directions, and offering general support as needed.

EDI Project Manager

Company: The LaSalle Network

Location: Chicago, IL

Posted Jul 10, 2025

Manage project timelines, budgets, and resource plans using PM tools. Collaborate with IT, Supply Chain, Finance, and Customer Service teams to define…

Regional Manager

Company: Highlands Vista Group

Location: Chicago, IL

Posted Jul 10, 2025

Organize monthly documentation for credit card payments and reimbursement invoices. Assist onsite teams with policy interpretation, compliance, and…

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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