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 - $5k sign-on bonus

Company: P&S

Location: Chicago, IL

Posted Aug 20, 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.

Business Analyst

Company: Crowe LLP

Location: Chicago, IL

Posted Aug 20, 2025

Ability to effectively communicate technical concepts to non-technical stakeholders. Currently pursuing a bachelor’s or master’s degree in one of the following…

Manager of Sales

Company: ODM Tool & Mfg. Co., Inc.

Location: McCook, IL

Posted Aug 20, 2025

Manage all aspects of the sales and marketing departments, and develop and execute the sales / marketing plans in conjunction with the President and CEO.

Construction Carpenter

Company: PM Construction

Location: Elk Grove Village, IL

Posted Aug 20, 2025

Operate hand tools, power tools, and heavy equipment safely. OSHA 10 or 30 certification preferred. Read and interpret blueprints, sketches, and construction…

Maintenance Worker (Plumber)

Company: St. Bernard's Hospital and Health Care Center

Location: Chicago, IL

Posted Aug 20, 2025

Perform plumbing preventative maintenance work and provide corrective plumbing repair work for hospital departments including off-site clinics and medical…

Truck Driver Class A

Company: Dominguez Transportation

Location: Chicago, IL

Posted Aug 20, 2025

Proven experience in truck driving with a valid commercial driver’s license (CDL). This role requires a strong commitment to safety, excellent driving skills,…

Unarmed Security Officer

Company: Per Mar Security Services

Location: Hinsdale, IL

Posted Aug 20, 2025

Must have personal own vehicle! . The selected individual will patrol and secure assigned premises as well as identify risks to staff and patrons.

Resource Coordinator Environmental Science Supervisor Manager Level EVS Support Services Environmental Full time Evenings

Company: Northwestern Medicine

Location: Chicago, IL

Posted Aug 20, 2025

Three to five years of experience in relevant field and Supervisory experience. We offer a wide range of benefits that provide employees with tools and…

Maintenance Class A/ Helper A

Company: Community Specialists

Location: Chicago, IL

Posted Aug 20, 2025

Obtain any require city or state certification necessary for maintenance of the property. Safe operation of cleaning equipment, power tools, and hand tools.

Software Development Engineer

Company: Expedia Group

Location: Chicago, IL

Posted Aug 20, 2025

Education: Bachelor’s degree in Computer Science, Software Engineering, or a related field or equivalent related professional experience.

Senior Concrete Finisher / Framer / Layout

Company: Ari Walsh

Location: Berwyn, IL

Posted Aug 20, 2025

Valid DL with a good driving record. Ability to lift up to 50lbs and be comfortable working in outdoor environments/various weather conditions.

Manager Oncology Pharmacy Operations - Outpatient

Company: Rush University Medical Center

Location: Chicago, IL

Posted Aug 20, 2025

Board certification in oncology (BCOP) preferred. 8.Participates in development, implementation, evaluation, and quality improvement of oncology services.

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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