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.

Spray Foam & Drywall/Plaster Installer

Company: Eclipsyum

Location: Schiller Park, IL

Posted Sep 29, 2025

Previous experience in spray foam insulation, drywall installation, plastering, or painting. Install, maintain, and repair drywall and plaster surfaces.

General Labor/Construction

Company: International Leak Detection

Location: Chicago, IL

Posted Sep 30, 2025

Must possess a valid driver’s license with a clean driving record. International Leak Detection is currently seeking mature, responsible field technician…

Welder

Company: Tradesmen International, Inc.

Location: Franklin Park, IL

Posted Sep 30, 2025

Ability to read and interpret blueprints and technical drawings. Perform TIG welding on various custom fabrication projects. 401(k) profit-sharing savings plan.

Client Support Representative

Company: RoofingSource

Location: Niles, IL

Posted Sep 29, 2025

Hungry, resourceful, and looking to develop their skillset within the sales and operations field and learn more about commercial roofing, construction, and HVAC…

Facilities Maintenance Technician(WELDER)

Company: Central Transport

Location: Hillside, IL

Posted Sep 30, 2025

*Carpentry *– install floor tiles including ceramic and VCT, repair and hang metal/wood doors, masonry repairs, concrete repairs, drywall, and other trades.

Heating, Ventilation, and Air Conditioning Technician

Company: Air Blue Heating & Cooling

Location: Wheeling, IL

Posted Sep 30, 2025

Occasional miscellaneous HVAC and mechanical equipment. Honest, dependable, and knowledgeable technician. EPA Certified (other licenses a plus).

Machinist II ( 1,000 Sign On Bonus)

Company: American Roller Company

Location: Riverdale, IL

Posted Sep 29, 2025

*Technical Skills:* Ability to read technical drawings and use micrometers, gauges, and other precision measuring tools. Keep the working area clean and safe.

Fabricator / Welder

Company: JX Truck Center

Location: Elmhurst, IL

Posted Sep 30, 2025

A valid driver's license with a 3 year history required. Ability to read and interpret blueprints or technical drawings. Medical - PPO and HDHP options.

Full Stack Software Engineer

Company: Unison Consulting, Inc.

Location: Chicago, IL

Posted Sep 30, 2025

This is a permanent fulltime onsite position (hybrid work environment). Net applications. Our ideal candidate is a highly motivated individual who is looking to…

Machine Operator I - 2nd Shift

Company: Ferrara Candy Company, Inc.

Location: Forest Park, IL

Posted Sep 30, 2025

Loads trays / boards on truck to be sent to the polishing room. Ability to operate and troubleshoot problems with all necessary process equipment.

Entry Level Business Analyst

Company: Simpalm

Location: Chicago, IL

Posted Sep 29, 2025

Applicants from non-IT and non-computer science background, having good communication and analytical skills can also apply. Excellent verbal and written skills.

Pre-Sales Engineer III

Company: Proven Business Systems LLC

Location: Tinley Park, IL

Posted Sep 30, 2025

Valid driver’s license and reliable form. Partner with sales and leadership teams to design, refine, and continuously improve assessment methodologies, driving…

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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