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.

[USA]coach/ops mgr trainee

Company: Walmart

Location: Paris, IL

Posted Jan 23, 2025

The role involves leading and developing teams effectively through teaching, training, and active listening. This includes touring stores, providing feedback, and communicating with associates at all levels regarding store operations and business initiatives. The individual will model exceptional customer service standards, resolve customer issues, and drive financial performance and sales. They will also provide supervision and development opportunities for hourly associates, ensure compliance with company policies, and uphold Walmart's values and standards of ethics and integrity.

Global Security Operations Center Operator

Company: Discover

Location: Riverwoods, IL

Posted Jan 23, 2025

Discover is offering a job opportunity in the Global Security Operations Center (GSOC) Operator role. The position involves evaluating and reporting on hazards and threats, dispatching security officers, and monitoring access control, alarm, and surveillance systems. The ideal candidate should have excellent communication skills, 2+ years of experience in law enforcement, military, corporate security, intelligence, business, or emergency management, and an associates degree in relevant fields. The role requires working from 6:00 a.m. to 2:00 p.m. CDT, Wednesday to Sunday. Discover values diversity and offers competitive compensation, benefits, and a collaborative culture.

Financial Advisor - Career Change Opportunity

Company: Edward Jones

Location: Bloomington, IL

Posted Jan 23, 2025

Edward Jones is offering a career as a financial advisor, a role that involves partnering with clients to achieve their long-term financial goals. As a financial advisor, you'll develop and grow your own practice, supported by a robust network. The company values an inclusive environment and unique professional backgrounds. The role involves building relationships, understanding clients' needs, and creating personalized strategies. The compensation package includes paid training, salary for the first five years, and opportunities for commissions, profit sharing, and incentive travel. The company also offers comprehensive benefits and a culture of continuous improvement and professional development.

Entrepreneurial Agent Development Specialist - IL / IN

Company: The Auto Club Group

Location: Aurora, IL

Posted Jan 23, 2025

The Auto Club Group is currently hiring for a full-time Entrepreneurial Agent (EA) Development Specialist position. The role involves serving as a business consultant and partner to Entrepreneurial Agents, providing tactical and strategic support. Key responsibilities include assisting in the development and implementation of agency business goals, supporting the acquisition of new business, and ensuring agent productivity and growth. The successful candidate will also be responsible for building trust with assigned EAs and maintaining strong relationships with internal and external partners. The company offers a competitive salary, comprehensive benefits, and opportunities for professional development. Required qualifications include a valid driver's license, appropriate state licenses, and relevant work experience in insurance sales leadership and agent development.

Rail Track Maintainer

Company: CN

Location: Champaign, IL

Posted Jan 23, 2025

CN is offering a Rail Track Maintainer position with a starting hourly rate of $32.28. The role involves inspecting, repairing, and replacing rails, ties, switches, and ballasts, working outdoors in various weather conditions. CN emphasizes safety, integrity, and teamwork. Benefits include an ESIP, Pension, Benefits, RRB, and other perks. The job requires relevant experience, a valid driver's license, and ability to lift up to 70 pounds. Successful candidates will undergo a 5-week paid training program at CN's campus in Homewood, IL.

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.

Manager Solution Consulting e-invoicing

Company: Thomson Reuters

Location: Chicago, IL

Posted Jan 23, 2025

Thomson Reuters is seeking a Solution Consultant for the global solutions team, based in the West region. The role involves managing a regional solutions team, acting as a go-to point for solutions staff, and having a 30/50% management and 50/70% hands-on/projects workload split. Responsibilities include managing training plans, workload, and ensuring staff have necessary tools and knowledge. The role also involves regular interaction with regional team members, first-line management tasks, and maintaining relevant data in commercial toolkits. Required qualifications include a minimum of 2 years of relevant experience, relationship-building skills, experience with large complex organizations, fluency in English and French, and professional services experience. The compensation package includes a base salary of $155,000 and a variable bonus of $25,000. Thomson Reuters offers comprehensive benefits, including wellbeing, culture, learning & development, social impact, and purpose-driven work.

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.

Related Pages