Flexible Work Schedule Jobs in Chicago, IL

75,610 open positions · Updated daily

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

Senior Systems Engineer – VDI and Virtualization

Company: Interactive Brokers

Location: Chicago, IL

Posted Jan 23, 2025

Interactive Brokers Group Inc, a global financial services company, is seeking a hybrid role for a Global Windows Platform and Services team member. The role involves planning, designing, automating, orchestrating, and implementing VMware and HPE solutions in data centers. The ideal candidate should have extensive experience in designing and implementing virtual desktop environments using industry-standard on-prem and cloud virtualization technologies. They should also have advanced knowledge of VMware Horizon View, vSphere, and high-availability environments, as well as expert understanding of networking concepts, data backup, recovery, and replication. Proficiency in PowerShell, PowerCLI, Python, Terraform, Ansible, and cloud platforms like Azure and AWS is required. The role offers a competitive salary, bonuses, stock grants, retirement plans, health benefits, paid time off, and learning opportunities.

Shift Lead

Company: Walgreens

Location: Arlington Heights, IL

Posted Jan 23, 2025

The role involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Key responsibilities include managing deliveries, processing returns and refunds, maintaining store cleanliness, and assisting with pharmacy tasks. The position requires leadership experience, fluency in English, and knowledge of store systems. The role is based in Arlington Heights, IL, with a salary range of $17 - $19 hourly.

Pharmacy Technician / Pharm Tech Apprenticeship

Company: Walgreens

Location: Alton, IL

Posted Jan 23, 2025

Walgreens is transforming its pharmacy technician roles to a more patient-centric environment. As a Walgreens Pharmacy Technician or Apprentice, you'll interact with customers, develop strong patient relationships, and have access to the latest technology to grow your career. Walgreens offers an 'earn while you learn' Pharmacy Technician Training Program, recognized by ASHP and the Department of Labor, which guides you towards becoming a PTCB Certified Pharmacy Technician. The role involves assisting pharmacists, using pharmacy systems, maintaining customer service, and participating in inventory management. Fluency in English, good math and computer skills, and preferably prior retail or Walgreens experience are required. PTCB certification is preferred but not mandatory.

Customer Service - Donor Support Technician

Company: CSL

Location: Gurnee, IL

Posted Jan 23, 2025

The job involves preparing the donor and equipment for the pheresis process, monitoring the donor and process, responding to alarms, recording incidents using a PDA, maintaining a clean work environment, and ensuring accurate data recording. The role requires a high school diploma, at least 3 months of relevant work experience, and the ability to perform basic math calculations. The work environment is fast-paced, with occasional lifting of up to 25 pounds. Benefits include health care options, life insurance, disability coverage, a 401(k) program, PTO, and paid holidays. CSL Plasma is a global organization committed to collecting human plasma for those with rare and serious diseases.

Certified Pharmacy Technician

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

Shift Lead

Company: Walgreens

Location: Villa Park, IL

Posted Jan 23, 2025

Senior Merchandiser - Procurement

Company: Sysco

Location: West Dundee, IL

Posted Jan 23, 2025

The job posting is for a procurement position at US1292 Buckhead Meat Midwest Inc.-Illinois Division. The role involves managing inventory needs, placing purchase orders, negotiating with suppliers, and ensuring timely product delivery. The ideal candidate should have a high school diploma or equivalent, 3 years of purchasing experience, and proficiency in Microsoft Office. They should also have excellent organizational skills and AS400 experience is preferred. The role offers opportunities for growth and professional development within Sysco, a global leader in foodservice distribution.

Paid Social Marketing Manager

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

The job involves managing a multimillion-dollar paid social marketing budget, developing strategies to support sales efforts, and driving customer acquisition and retention. The role requires a strong technical background, experience in digital marketing, and the ability to analyze data and A/B test. The individual will lead internal social teams, manage agency relationships, and stay updated on industry trends. They will also work cross-functionally to support key initiatives and product launches.

Pharmacy Customer Service Associate

Company: Walgreens

Location: Quincy, IL

Posted Jan 23, 2025

The job description involves delivering a distinctive and delightful customer experience, including greeting customers, offering assistance, resolving issues, and ensuring positive interactions. The role also includes operating a cash register, processing prescriptions under pharmacist supervision, maintaining store cleanliness, and handling inventory. The employee is expected to adhere to company policies, maintain knowledge of healthcare and pharmacy, and complete necessary training and certifications. Fluency in English, flexibility for various shifts, and good math and computer skills are preferred.

Shift Lead

Company: Walgreens

Location: McHenry, IL

Posted Jan 23, 2025

Frequently Asked Questions

What are typical salary ranges for flexible work schedule roles at different seniority levels?
Entry‑level (0‑2 years) $60k–$80k; Mid‑level (2‑5 years) $80k–$120k; Senior (5‑10 years) $120k–$180k; Lead/Principal (10+ years) $180k–$250k. International remote roles may have adjusted ranges such as $40k–$60k in emerging markets, reflecting local cost of living while maintaining equity.
What key skills and certifications are required for flexible work schedule positions?
Technical: Proficiency in Git, Docker, Kubernetes, and cloud platforms (AWS Certified Solutions Architect, Google Cloud Professional Data Engineer, or Azure Solutions Architect). Agile and project tools: Jira, Confluence, and automated testing frameworks. Soft skills: asynchronous communication, cultural competence, self‑management, and time‑zone coordination. Certifications like Certified Scrum Master (CSM), ITIL Foundation, and PMP are highly regarded for product and project roles.
Is remote work always an option for flexible schedule roles?
Most flexible schedule positions offer 100% remote or hybrid arrangements, with occasional on‑site requirements for quarterly collaboration or training. Companies often specify the percentage of remote work (e.g., 80% remote, 20% on‑site) and provide stipends for home‑office equipment. Applicants can verify the remote policy in the job description or during the interview.
What career progression paths exist within flexible work schedule roles?
Typical paths include: Junior Engineer → Senior Engineer → Tech Lead → Principal Engineer → Engineering Manager; or Product Manager → Senior Product Manager → Director of Product → VP of Product. Lateral moves into architecture, security, or data science are common for professionals seeking broader impact while maintaining flexible arrangements.
What are the current industry trends affecting flexible work schedule jobs?
Key trends: growth of asynchronous communication tools (e.g., Loom, Notion), AI‑driven workflow automation (e.g., GitHub Copilot, ChatGPT for code review), distributed version control at scale, micro‑tasking platforms, flexible sprint lengths, well‑being metrics integration, and digital nomad visas supporting cross‑border talent. Companies are also investing in continuous learning portals and remote‑first hiring practices.

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