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.

Overnight Security Guard: Full-Time

Company: PalAmerican Security

Location: Chicago, IL

Posted Jul 08, 2025

As an Unarmed Security Guard, you will play a crucial role in maintaining the safety and security of multiple sites, ensuring a positive atmosphere for…

Class A Truck Driver

Company: K&B Transportation

Location: Chicago, IL

Posted Jul 08, 2025

We offer our OTR truck drivers one of the best health insurance policies in the industry. Road Warrior drivers earn $.70 CPM. 4 Weeks Out / 5 Days Off.

Staff Software Engineer

Company: GE HEALTHCARE

Location: Chicago, IL

Posted Jul 08, 2025

5 years of experience in design and development of software architecture using established design patterns. 5 years of experience in object oriented design and…

HVAC Service Technician

Company: Aire Serv

Location: Brookfield, IL

Posted Jul 08, 2025

Valid driver's license and clean driving record. We employ a front-line service system that, when followed, will consistently generate 5-star reviews.

Project Manager - Multifamily Developer

Company: Michael Page

Location: Chicago, IL

Posted Jul 08, 2025

The Project Manager is responsible for scheduling, oversight of construction and communication with project team. Bonus per project (up to 12%).

Spot Welder

Company: Thunder Metal Works

Location: Broadview, IL

Posted Jul 08, 2025

Competent in operating power tools safely and effectively in a construction environment. The ideal candidate will have experience in welding processes and the…

Director of Annual Giving & Alumni Engagement

Company: Sigma Alpha Epsilon Foundation

Location: Evanston, IL

Posted Jul 08, 2025

This positions lead the strategy, design, execution, and analysis of annual giving campaigns and initiatives through direct mail, email, phone, social media,…

HVAC Refrigeration Service Technician

Company: Nextech

Location: Downers Grove, IL

Posted Jul 08, 2025

EPA certification and a valid driver’s license. Diagnose and repair HVAC/R systems, including electrical, mechanical, and electronic components.

HVAC Technician

Company: Goodberlet Home Services

Location: Oakbrook Terrace, IL

Posted Jul 08, 2025

Valid driver's license with a clean driving record. Operate company vehicles safely as a van driver to transport tools and equipment to job sites.

Welder Mig/Tig

Company: Thunder Metal Works

Location: Broadview, IL

Posted Jul 08, 2025

Tig/Mig welder is responsible for being able to read blueprints, make basic fixtures, and weld parts together to a certain standard.

HVAC Service Technician

Company: Aire Serv

Location: Berkeley, IL

Posted Jul 08, 2025

Valid driver's license and clean driving record. We employ a front-line service system that, when followed, will consistently generate 5-star reviews.

Brand Ambassador - Sales Associate

Company: Jonathon Wesley

Location: Itasca, IL

Posted Jul 08, 2025

Safe driving record, valid driver’s license, and dependable transportation with valid insurance. Minimum requirement of a high school diploma, bachelor’s degree…

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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