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.

Shift Supervisor Trainee

Company: CVS Health

Location: Godfrey, IL

Posted Jan 23, 2025

GYNECOLOGY-ONLY

Company: Progressive Care for Women

Location: Chicago, Illinois

Posted Jan 23, 2025

A gynecology-only private practice in downtown Chicago, affiliated with an academic medical center, is seeking a full-time physician. The role offers a great work-life balance with office-based gynecology and in-office procedures with mobile anesthesia. The practice is centrally located, allowing easy access to the lakefront, shopping, restaurants, and cultural attractions. The ideal candidate should be board-eligible or board-certified. The position offers a competitive salary, health insurance, and a profit-sharing plan.

(USA) Personal Shopper - Sam's

Company: Walmart

Location: Addison, IL

Posted Jan 23, 2025

The job involves developing and supporting membership by providing information on benefits, promoting products, processing memberships, and meeting sales goals. Safety of the facility is maintained by following safety standards and procedures. Member orders are fulfilled by reviewing, pulling items, scanning, wrapping, and palletizing them. Work assignments are completed by collaborating with team members and adapting to change. Member service is provided by acknowledging needs, assisting with purchasing decisions, and promoting company products. Competitive pay, bonuses, and various benefits are offered, including health, financial, and time-off benefits. The hourly wage range is $18.00 to $25.00, with potential premiums based on specific circumstances.

Store Associate

Company: CVS Health

Location: Villa Park, IL

Posted Jan 23, 2025

CVS Health is seeking Retail Store Associates to join their team, emphasizing a human-centric approach to healthcare. The role involves providing excellent customer service, handling cashier duties, maintaining the sales floor, supporting store activities, and assisting in the pharmacy. The company offers competitive pay, comprehensive benefits, and opportunities for career growth. No prior retail experience is required, but a high school diploma is preferred.

Principal Data Science

Company: Discover

Location: Riverwoods, IL

Posted Jan 23, 2025

Pharmacy Technician

Company: CVS Health

Location: Rockton, IL

Posted Jan 23, 2025

Maintenance Utility Technician - Entry Level

Company: Kohl's

Location: Ottawa, IL

Posted Jan 23, 2025

The job posting is for a Utility Technician role at Kohl's, working Monday through Friday from 4p to 2a. The role involves maintaining and repairing equipment and machinery, monitoring and stocking as needed, completing daily cleaning checklists, performing diagnostics, troubleshooting, and operating power equipment. Additional responsibilities include assisting with repairs, preventative maintenance, and minor projects, as well as handling tasks like painting, changing light bulbs, and removing trash. The required skills include basic mechanical aptitude. Kohl's offers a range of benefits including work-life balance, health & wellness programs, savings & retirement benefits, insurance programs, and assistance for life events. The pay range is $18.05 - $23.45.

Staff Pharmacist

Company: CVS Health

Location: Marion, IL

Posted Jan 23, 2025

Principal Manufacturing Engineer

Company: Eaton

Location: Rock Island, 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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