Flexible Scheduling Jobs in Chicago, IL

27,637 open positions · Updated daily

Looking for Flexible Scheduling jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Scheduling position in the Chicago, IL area.

Enterprise Product Risk Lifecycle Analyst

Company: paypal

Location: Chicago, IL

Posted Jul 30, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Licensed Customer Service Representative- Insurance Agency

Company: Allstate Insurance - Jackson and Associate Agency

Location: Chicago, IL

Posted Jul 30, 2025

Utilize agency tools and technology to track customer interactions and follow-ups. *Hands-On Training & Licensing Support* (if not already licensed).

Service Associate - Evening Shifts - Housekeeping

Company: Loyola University Health System

Location: Melrose Park, IL

Posted Jul 31, 2025

Supporting quality patient care services by maintaining a clean, sanitary, safe and orderly environment for health care providers as well as patients and…

Machine Operator 1st and 2nd Shift

Company: JobSquad Staffing Solutions

Location: Stone Park, IL

Posted Jul 30, 2025

Responsible for manufacturing, distributing and consistently maintaining safe and quality food by following good manufacturing practices, allergen controls,…

Special EDU Teacher

Company: Kaleidoscope Education Solutions

Location: Chicago, IL

Posted Jul 30, 2025

Bachelor's degree in Special Education or related field. Your own personal connection in our office whenever you need support or have questions!

Enterprise Product Risk Lifecycle Analyst

Company: PayPal

Location: Chicago, IL

Posted Jul 31, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Substitute Teacher

Company: Swing Education

Location: Chicago, IL

Posted Jul 31, 2025

No early morning phone calls. $180-$240 per day depending on school, location, and certification. We support substitute teachers with helpful tools, optional…

Sr. Manager, eCom & Customer Marketing Ops

Company: Kraft Heinz Company

Location: Chicago, IL

Posted Jul 31, 2025

Partner with Brand Teams to identify and develop strategy and creatives for retail media and shopper marketing programs that align with both customer objectives…

Manager, Customer Success

Company: Intercom

Location: Chicago, IL

Posted Jul 30, 2025

You will internally influence cross-functional partners to ensure we are driving positive customer outcomes. 2+ years of experience in a leadership role within…

PROJECT COORDINATOR

Company: City of Chicago

Location: Chicago, IL

Posted Jul 31, 2025

Graduation from an accredited college or university with a bachelor's degree in public or business administration, social sciences, planning, or a related field…

Software Engineer

Company: Getty Images

Location: Chicago, IL

Posted Jul 31, 2025

A Bachelor’s degree, or foreign equivalent, in Information Systems, Computer Science, or a closely related field of study. Serve as part of on-call rotation.

Healthcare Project Manager

Company: WM

Location: Chicago, IL

Posted Jul 31, 2025

Education: Bachelor's Degree (accredited) in Environmental Sciences, Accounting, Business or related field, or in lieu of degree, High School Diploma or GED (…

Frequently Asked Questions

What are typical salary ranges by seniority for Flexible Scheduling roles?
Entry‑level Scheduling Coordinators earn $45,000–$60,000 annually, mid‑level Workforce Planners command $60,000–$90,000, and senior Scheduling Managers or Operations Directors can reach $90,000–$120,000 or more, depending on company size and region.
What skills and certifications are most valuable in Flexible Scheduling positions?
Proficiency in workforce‑management platforms such as Kronos Workforce Central, SAP SuccessFactors, and Oracle Workforce Management is essential. Strong analytical skills in SQL and Tableau, coupled with experience using Agile or Six Sigma methodologies, give an edge. Certifications like Certified Workforce Planning Professional (CWPP), Six Sigma Green Belt, or a project‑management credential (PMP) are highly regarded.
Is remote work available for Flexible Scheduling roles?
Yes—over 70% of the listings support fully remote or hybrid arrangements, especially in tech, logistics, and customer‑support sectors. Remote positions typically offer a pay adjustment based on regional cost‑of‑living indexes.
What career progression paths exist within Flexible Scheduling?
A common trajectory starts at Scheduling Coordinator, moves to Workforce Planner or Shift Scheduler, then to Scheduling Manager or Operations Analyst, and can culminate in Director of Workforce Optimization or Chief Workforce Officer, with increased responsibility over strategy, analytics, and cross‑functional leadership.
What industry trends are shaping the future of Flexible Scheduling?
Artificial‑intelligence forecasting, real‑time labor analytics, and blockchain‑based time‑tracking are driving the next wave of scheduling solutions. Companies are adopting predictive shift‑optimization tools, integrating gig‑worker platforms, and expanding continuous‑learning modules to upskill scheduling talent.

Related Pages