Flexible Work Schedule Jobs in Chicago, IL

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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.

Sales Representative

Company: Sysco

Location: Oak Lawn, IL

Posted Jan 23, 2025

Sysco Chicago, Inc. is seeking a full-time Outside Sales professional for the Oak Lawn, Elmhurst, and LaGrange territories. The role involves promoting the company's products and services, building relationships with new and existing accounts, and achieving sales and profit goals. Key responsibilities include developing new business, penetrating existing accounts, and minimizing lost business. The position offers a competitive base salary, bonus, promotional incentives, car allowance, and a robust benefits package. Qualifications include a Bachelor's degree in Business, Sales, Marketing, Hospitality, Culinary Arts or related discipline, or equivalent experience. Preferred qualifications include bilingualism, restaurant management, foodservice outside sales, and chef experience. The role requires a valid driver's license, clean driving record, and current automobile insurance.

Shift Lead

Company: Walgreens

Location: Crestwood, IL

Posted Jan 23, 2025

Customer Service Associate

Company: Walgreens

Location: Peoria, IL

Posted Jan 23, 2025

The text describes a job role that involves delivering a distinctive and delightful customer experience. The responsibilities include engaging customers, resolving issues, and providing efficient checkout service. The role also involves maintaining store cleanliness, implementing asset protection procedures, and ensuring compliance with regulated product laws. The job requires fluency in English and a flexible schedule, including evenings and weekends. Preferred qualifications include prior retail experience and familiarity with Walgreens. The role offers a salary range of $15 - $17.5 per hour.

Pharmacy Intern

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

The job involves learning to provide excellent patient experience by assisting pharmacists and team members, adhering to regulations. Key responsibilities include engaging customers, resolving issues, and maintaining a positive customer experience. The role also involves assisting in pharmacy operations, such as prescription processing, inventory management, and maintaining a clean, orderly pharmacy. The ideal candidate is a current pharmacy student, fluent in English, and willing to work flexible hours. Prior retail experience and good math skills are preferred.

Pharmacy Technician / Pharm Tech Apprenticeship

Company: Walgreens

Location: Woodstock, IL

Posted Jan 23, 2025

Walgreens is transforming its pharmacy technician roles to a more patient-centric environment. As a 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 adhering to state and federal regulations. Walgreens provides training and opportunities for personal development, including PTCB certification and continuing education credits.

Customer Service Associate

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

Specialty Pharmacy Technician

Company: Walgreens

Location: Gurnee, IL

Posted Jan 23, 2025

The role involves assisting the pharmacist in the practice of pharmacy, adhering to state, federal, and company regulations. Duties include using pharmacy systems for patient and drug information, processing prescriptions, and maintaining pharmacy systems. The individual will also engage customers, resolve issues, and ensure a positive experience. They will report errors immediately, adhere to company policies, and assist in inventory management. PTCB or ExCPT certification is preferred, and the role requires a flexible schedule. The position involves maintaining a clean, neat, and orderly pharmacy department, and developing relationships with the local medical community.

Supply Chain Analyst, Transportation Optimization

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

The Supply Chain Analyst on the last mile transportation team is responsible for conducting moderately complex analysis of information, problems, and data. This role involves working under general supervision, making recommendations for senior staff review, tracking and measuring the impact of implemented solutions, and communicating risks with mitigation recommendations. The analyst also builds internal/external relationships, resolves moderately complex issues, and recommends process improvements. Walgreens, the employer, is a leading healthcare, pharmacy, and retail company with a focus on community care and omnichannel experiences.

Repack Associate

Company: Sysco

Location: South Elgin, IL

Posted Jan 23, 2025

Customer Service Associate

Company: Walgreens

Location: Aurora, IL

Posted Jan 23, 2025

Store Manager

Company: Walgreens

Location: Oakbrook, 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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