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.

SAS in Schnucks - Part Time Retail Merchandiser

Company:

Location: Upper Alton, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a detail-oriented Reset Merchandiser. The role involves handling product movement at retail, ensuring the latest products match the new plan. This job offers a competitive wage of $15.00 per hour, growth opportunities, and benefits that can be customized to meet family needs. The ideal candidate is 18 years or older, has reliable transportation, a valid driver's license, and is comfortable with physical work involving moving, bending, standing, and lifting up to 25lbs.

Sales and Service Rep - CLASS B ROUTE DRIVER

Company:

Location: Elgin, IL

Posted Jan 23, 2025

Safety-Kleen in Elgin, IL is recruiting a Sales and Service Route Driver Trainee. The role involves training to drive a Class B box truck for onsite service of parts washer machines, collection of hazardous waste, and product/service sales within a defined route. Safety-Kleen will cover the cost of obtaining a CDL. The company, a subsidiary of Clean Harbors, is a leading provider of environmental, energy, and industrial services. They prioritize health and safety, offer competitive pay, comprehensive benefits, and opportunities for growth. Key responsibilities include maintaining safety, visiting customer sites, servicing machines, upselling, and complying with regulations. Required qualifications include a Class B CDL, basic computer and math skills, strong communication, customer service skills, and passing a background check, drug test, and physical.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Lake Zurich, 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, standing, and lifting up to 25lbs.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Naperville, 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.

Retail Sales Merchandiser

Company:

Location: Rosemont, 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 $15.80 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 - Overnight

Company:

Location: Villa Park, 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 $15.80 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.

Retail Data Collector

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

Retail Data Collector

Company:

Location: Schaumburg, IL

Posted Jan 23, 2025

Outside Sales Reps Hiring Immediately

Company:

Location: Orland Park, 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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