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.

Custodian

Company: Chicago Children's Advocacy Center

Location: Chicago, IL

Posted Jul 30, 2025

To maintain the ChicagoCAC as a clean and safe environment for all clients, employees, partners and guests. The Custodian has a low-level range of discretion…

Janitorial Crew Member (Part-Time)

Company: Sertoma Star Services

Location: Chicago, IL

Posted Jul 30, 2025

To comply with state regulations ensuring the safety and well-being of the individuals we support, we require all potential employees to undergo a thorough…

Product Marketing Manager

Company: Expedia Group

Location: Chicago, IL

Posted Jul 30, 2025

With a deep knowledge of the Transport product space, you will champion customer-centric products and communicate the product vision, craft insights to help…

Marketing Specialist

Company: Northwestern Medicine

Location: Chicago, IL

Posted Jul 30, 2025

We consider this on a case-by-case basis and follow all state and federal guidelines. Undergraduate degree in Marketing or related field.

Local Truck Driver

Company: Wylie Transit LLC

Location: Chicago, IL

Posted Jul 30, 2025

Valid commercial driver's license (CDL) with appropriate endorsements (Tanker endorsement preferred). Proven experience in truck driving or as a delivery driver…

Solutions Architect, Retail, Google Cloud

Company: Google

Location: Chicago, IL

Posted Jul 30, 2025

Bachelor's degree in Computer Science, a related engineering field, or equivalent practical experience. A key task is to work with customers, field teams,…

Marketing Specialist - University Relations

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jul 30, 2025

Bachelor's degree in communications, Marketing, or related field. The person in this role is expert in all facets of successful marketing communications…

Class A Truck Driver

Company: 10 Roads Express

Location: Bedford Park, IL

Posted Jul 30, 2025

12+ months of verifiable tractor trailer driving experience. 10 Roads Express is hiring Class A CDL truck drivers to run various routes and cover openings in…

Senior Income Tax Analyst

Company: Amrize Building Materials US

Location: Chicago, IL

Posted Jul 30, 2025

Working knowledge of federal and state corporate income tax compliance. The Senior Income Tax Analyst, Tax Reporting will play a key role in the preparation and…

Ambulatory RN 2 - Adult and Pediatrics Population

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jul 30, 2025

Current license and credentials by the state they are assigned. 6.Utilizes evidence-based ambulatory care nursing interventions during clinical visits,…

Senior Marketing Specialist

Company: Northwestern Medicine

Location: Chicago, IL

Posted Jul 30, 2025

Minimum 3 years of experience in related field. Undergraduate degree in Marketing or related field. We offer a wide range of benefits that provide employees…

Janitor

Company: Newly Weds Foods- Broadview, IL

Location: Broadview, IL

Posted Jul 30, 2025

Maintain work area in a clean and orderly manner so that it can receive incoming baskets of trash. It is this worker’s professional responsibility to clean 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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