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.

Customer Service Associate

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

Enterprise Sales Manager

Company: Taboola

Location: Chicago, IL

Posted Jan 23, 2025

Taboola, the world's number 1 discovery platform, is seeking an Enterprise Advertising Sales Manager for its Chicago team. The role involves building and managing long-term strategic partnerships with Tier 1 Brands and agencies across the midwest. Key responsibilities include prospecting, networking, pipeline development, new client acquisition, client retention, and achieving revenue goals. The ideal candidate should have a Bachelor's degree, 4+ years of digital advertising sales experience, existing relationships in Financial Services, Health, Home and Garden, Auto, Retail, and Tier I Agencies, deep knowledge of advertising and technology, strong business acumen, and emotional intelligence. Taboola offers a collaborative, high-growth environment with competitive benefits.

Shift Lead

Company: Walgreens

Location: Chicago, 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 Chicago, IL, with a salary range of $17 - $19 per hour.

Shift Lead

Company: Walgreens

Location: Tinley Park, IL

Posted Jan 23, 2025

Customer Service Associate

Company: Walgreens

Location: Downers Grove, 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.

Shift Lead

Company: Walgreens

Location: Downers Grove, IL

Posted Jan 23, 2025

PRN Pharmacist - Community

Company: UnitedHealth Group

Location: Rock Island, IL

Posted Jan 23, 2025

Community Management Intern

Company: Walgreens

Location: Orland Park, IL

Posted Jan 23, 2025

The job involves providing an extraordinary customer experience in a retail store setting, engaging customers, resolving issues, and modeling customer service best practices. Responsibilities include operating cash registers, managing inventory, maintaining store cleanliness, and ensuring compliance with regulations. The role also involves learning from store managers, competitors, and customers, and participating in team challenges. Basic qualifications include being a student in the senior year towards a Bachelor's degree, fluency in English, and flexibility for various shifts.

Wealth Management-Chicago-Administrative Assistant- Support

Company: Goldman Sachs

Location: Chicago, IL

Posted Jan 23, 2025

The Goldman Sachs Group, Inc., a renowned global investment firm, is seeking an administrative professional for a senior role in Chicago. The position involves providing complex support to executives, coordinating meetings, managing travel, and handling sensitive information. The ideal candidate should possess excellent communication skills, high attention to detail, and strong organizational abilities. A minimum of 3-5 years of experience is preferred. The salary range is $70,000-$110,000, with potential for a discretionary bonus. Goldman Sachs offers competitive benefits and a positive work environment.

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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