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.

Equity Accountant

Company: Google

Location: Chicago, IL

Posted Jul 28, 2025

Bachelor's degree in Accounting, Finance, Business, a related field, or equivalent practical experience. From developing forward-thinking analysis to generating…

Financial Controller

Company: The Mitchell Group

Location: Niles, IL

Posted Jul 28, 2025

Lead the accounting team in maintaining double-entry bookkeeping practices. Supervise accounts payable and accounts receivable functions to maintain efficient…

Precision CNC Machinist

Company: Janler

Location: Chicago, IL

Posted Jul 28, 2025

Mastercam programming or 5-axis experience, a plus - we will train! Clean, air-conditioned work environment in a modern 20,000 sq. ft. facility.

Staff Accountant

Company: Hogsalt Headquarters

Location: Chicago, IL

Posted Jul 28, 2025

Prepare and file city and state monthly and annual sales tax returns. Compile and analyze financial information to prepare entries to accounts, such as general…

Senior Presentation Associate

Company: Sealed Air

Location: Chicago, IL

Posted Jul 28, 2025

Able to troubleshoot more complex or advanced tasks, equipment or software concerns on own; understands when to escalate a problem to a supervisory level.

PROJECT MANAGER

Company: City of Chicago

Location: Chicago, IL

Posted Jul 28, 2025

The position involves the application and integration of comprehensive project controls to the design and construction process beginning in the project planning…

Customer Service Representative - Durable Medical Equipment

Company: Advance Medical Equipment, Inc

Location: Chicago, IL

Posted Jul 27, 2025

Complies with all current government/state regulations and professional standards involving patient care and information intake, as well as all applicable…

Registered Nurse (RN) Licensed Practical Nurse (LPN) ALL SHIFTS AVAILABLE

Company: Elevate Care Chicago North

Location: Chicago, IL

Posted Jul 26, 2025

Comprehensive Patient Care – Assess, plan, implement, and evaluate care plans for residents based on their health needs.

Pharmacist Per Diem - Overnight Shift

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jul 26, 2025

Licensed or license-eligible in the State of Illinois. Key responsibilities also include coordinating timely medication delivery to nursing units, providing…

Sales Associate - Car Wash

Company: Jet Brite

Location: Northlake, IL

Posted Jul 28, 2025

Use and develop critical thinking, listening, and technical skills while supporting and collaborating with team members. At least 16 years of age.

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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