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.

Customer Service Associate

Company: Walgreens

Location: Glendale Heights, 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.

Shift Lead

Company: Walgreens

Location: Tinley Park, IL

Posted Jan 23, 2025

The job involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Responsibilities also include coaching team members, maintaining store cleanliness, and complying with company policies. The role requires leadership experience, fluency in English, and knowledge of store systems. Preferred qualifications include experience with store inventory control.

Shift Lead

Company: Walgreens

Location: Skokie, 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 Skokie, IL, and the salary range is $17 - $19 hourly.

Product Support Advisor Supervisor

Company: Sysco

Location: Arlington Heights, IL

Posted Jan 23, 2025

Sysco, the global leader in foodservice distribution, is seeking a candidate for a supervisory role. The position involves overseeing Product Support Advisors, providing coaching, mentoring, and career development. Key responsibilities include creating and delivering presentations, driving specialty and sales initiatives, and resolving customer escalation issues. The ideal candidate should have 2-3 years of food sales or customer service experience, along with strong communication, organization, and problem-solving skills. Sysco offers opportunities for personal and professional growth, and is committed to equal opportunity employment.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Oak Lawn, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. The job pays $16.00 per hour, provides paid training, and offers benefits including medical, dental, and life insurance. Candidates must be 18+, have reliable transportation, and a valid driver's license, capable of physical work involving moving, bending, and lifting up to 25lbs.

Meat Trimmer

Company: Sysco

Location: West Dundee, IL

Posted Jan 23, 2025

QC/QA Supervisor

Company: Coca-Cola

Location: Crestwood, IL

Posted Jan 23, 2025

Reyes Coca-Cola Bottling is seeking a Quality Assurance Supervisor for a full-time position in a Manufacturing facility. The role involves directing QA employees, maintaining corporate and safety standards, establishing operational procedures, and focusing on cost reduction and efficiency. Benefits include medical, dental, vision, 401K match, PTO, and education reimbursement.

Certified Pharmacy Technician

Company: Walgreens

Location: Ottawa, 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 certification is preferred but not required. The role requires flexibility, good math and computer skills, and knowledge of store inventory control. The salary range is $17.5 - $21 hourly.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Sycamore, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. Benefits include $15.00 per hour, no weekends, early access to earned wages, and comprehensive benefits. The ideal candidate is detail-oriented, physically capable, and has reliable transportation.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Hoffman Estates, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. The job pays $16.00 per hour, provides paid training, and offers benefits including medical, dental, and life insurance. Candidates must be 18+, have reliable transportation, and a valid driver's license, capable of physical work involving moving, bending, and lifting up to 25lbs.

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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