Generous Paid Time Off Jobs in Chicago, IL

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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.

CHICAGO SOUTH LOOP ELECTRICIAN

Company: State of Illinois

Location: Chicago, IL

Posted Jul 09, 2025

Requires a valid driver’s license and the ability to travel to various sites/facilities. Under general supervision, receiving day-to-day guidance from the Chief…

Sous Chef

Company: Ramen - San

Location: Chicago, IL

Posted Jul 09, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

PT Sales Associate - North Michigan Ave Bloomingdales

Company: REISS

Location: Chicago, IL

Posted Jul 09, 2025

As part of our Chicago team, you'll be joining our Bloomingdale's concession in Chicago on a part time basis as our Sales Associate, who is responsible for…

Flash-Butt Welder

Company: RailWorks Corporation

Location: Chicago, IL

Posted Jul 09, 2025

A valid class A driver’s license and satisfactory driving record. Must have a valid driver’s license and the ability to gain Class-A CDL with 90-day.

Founding Graphic Designer

Company: Bulqit

Location: Chicago, IL

Posted Jul 08, 2025

Have enough technical skill to collaborate with developers—or even build simple tools and automations yourself.

Business System Analyst, HRIS Data - National Office (Remote)

Company: YMCA of the USA

Location: Chicago, IL

Posted Jul 09, 2025

Excellent communication and interpersonal skills; ability to translate technical concepts for non-technical audiences. YMCA Team Leader certification preferred.

Area Canvassing Sales Manager ($150k - $300k OTE)

Company: Zeo Energy

Location: Chicago, IL

Posted Jul 09, 2025

Our territory managers are responsible for generating leads inside their territory and maintaining business relationships with customers.

Senior Customer Support Specialist - Chicago, IL

Company: Uber

Location: Chicago, IL

Posted Jul 09, 2025

Facilitate driver sign-ups and communicating value proposition of driving with Uber, which may include proactive outreach.

Marketing Manager JN -072025-162685

Company: Goodwin Recruiting

Location: Chicago, IL

Posted Jul 08, 2025

Lead social media strategy: content planning, copywriting, publishing, boosting posts, community engagement, and performance tracking.

Oncology Infusion RN 2 - RUSH Cancer Center (Chicago) - Per Diem

Company: Rush Oak Park

Location: Chicago, IL

Posted Jul 09, 2025

Demonstrates accountability for own professional practice, including progress toward achievement of annual goals. Work Type: Restricted Part-Time (0. 1 FTE).

Janitorial Working Supervisor - (ACH)

Company: GDI Services Inc US

Location: Alsip, IL

Posted Jul 08, 2025

Cleaning restrooms, break-rooms, common areas, dusting and trash removal. Respond quickly and appropriately to all customer concerns or complaints.

Union Carpenter Foreman - Data Center Hot Aisle Containment

Company: Turner Construction Company

Location: Chicago, IL

Posted Jul 09, 2025

Supervise and develop trade employees, as assigned, including providing input on or completing performance appraisals. Address staff needs and resolve problems.

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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