Paid Time Off Jobs in Chicago, IL

72,501 open positions · Updated daily

Looking for Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect 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…

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.

Overnight Security Guard

Company: KH Security Inc.

Location: Chicago, IL

Posted Jul 08, 2025

*Must have your own vehicle. *Must have a valid Perc Card and 20 hours training certificate*. KH Security Inc. provides best in class security services for…

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 typical salary ranges for PTO roles by seniority?
Entry‑level PTO Analyst salaries range from $55,000 to $70,000 annually, mid‑level analysts earn $70,000 to $90,000, and senior PTO Program Managers or HRIS specialists command $90,000 to $120,000 plus bonus potential.
What skills and certifications are required for PTO positions?
Core skills include proficiency with HRIS platforms (Workday, SAP SuccessFactors, BambooHR), data analysis in Excel or Power BI, and regulatory knowledge of FMLA, ADA, and state leave laws. Certifications such as Certified Compensation Professional (CCP), HR Certification Institute (HRCI) HR-CP, or Workday HCM Associate enhance credibility.
Can PTO roles work remotely?
Yes, many PTO analysts and program managers operate fully remote, especially in tech firms. Remote work is supported by cloud‑based HRIS, secure VPNs, and collaboration tools like Slack and Microsoft Teams. Some roles still require occasional on‑site visits for policy rollout.
What are common career progression paths in PTO?
A PTO analyst can advance to Senior PTO Analyst, then to PTO Program Manager, followed by Director of Employee Benefits or HR Director roles. Lateral moves into broader HR analytics or compensation strategy are also common.
What industry trends are shaping PTO work?
Trends include the adoption of unlimited PTO policies, AI‑driven leave prediction models, integration of PTO data with wellness initiatives, and increased regulatory scrutiny on equitable leave practices. Companies also use data analytics to demonstrate ROI on PTO policies.

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