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: Peoria, IL

Posted Jan 24, 2025

Community Management Intern

Company: Walgreens

Location: Oak Park, IL

Posted Jan 24, 2025

Account Development Representative

Company: Billtrust

Location: Chicago, IL

Posted Jan 24, 2025

The job posting is for a Sales Development Representative position at Billtrust, located in Chicago. The role involves engaging new midmarket and enterprise accounts, cultivating opportunities, and supporting the sales team in achieving booking targets. The position offers structured onboarding, coaching, and guidance from sales executives. Key responsibilities include learning and conveying Billtrust's value proposition, executing program strategies, and collaborating with sales executives on prospecting plans. The ideal candidate should have a Bachelor's degree, at least one year of related experience, strong communication skills, and a desire to learn and grow. The base salary is $58,000 with an OTE of $80,000-$82,000. Billtrust offers a flexible work environment, professional development opportunities, and comprehensive benefits.

Emerging Store Manager

Company: Walgreens

Location: Woodstock, IL

Posted Jan 24, 2025

Pharmacy Technician / Pharm Tech Apprenticeship

Company: Walgreens

Location: Elgin, IL

Posted Jan 24, 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. The role offers training, personal development opportunities, and potential for eight college credit hours through the Walgreens pharmacy technician apprenticeship program.

Medical Device Warehouse Associate - 1st Shift - Starting rate $24.85/hr

Company: Stryker

Location: Itasca, IL

Posted Jan 24, 2025

Stryker is seeking a Supply Chain team member with 2+ years of experience. The role involves inspecting products, maintaining inventory records, and ensuring compliance with safety regulations. The company offers a fast-paced, autonomous work environment with opportunities for overtime and on-call duties. Stryker is recognized as a World's Best Workplace and a Best Workplace for Diversity. Benefits include comprehensive health insurance, financial benefits, and a wellbeing program. The ideal candidate is a self-starter, customer-oriented, and able to work flexible hours.

Pharmacy Customer Service Associate

Company: Walgreens

Location: Rockford, IL

Posted Jan 24, 2025

The role involves delivering a distinctive and delightful customer experience by engaging with customers, resolving issues, and providing efficient service. This includes registering sales, processing prescriptions under pharmacist supervision, maintaining store cleanliness, and assisting with inventory management. The position also requires knowledge of store systems, equipment, and adherence to company policies. PTCB certification is preferred but not mandatory. The role is open to applicants with diverse backgrounds, including those with arrest and conviction records, in compliance with the San Francisco Fair Chance Ordinance.

Associate Optometrist - Walmart

Company: Walmart

Location: Belleville, IL

Posted Jan 24, 2025

Community Management Intern

Company: Walgreens

Location: Hickory Hills, IL

Posted Jan 24, 2025

Principal, Compensation

Company: Walgreens

Location: Deerfield, IL

Posted Jan 24, 2025

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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