Flexible Work Arrangements Jobs in Chicago, IL

74,530 open positions · Updated daily

Looking for Flexible Work Arrangements jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Arrangements position in the Chicago, IL area.

Shift Supervisor Trainee

Company: CVS Health

Location: Godfrey, IL

Posted Jan 23, 2025

Client Implementations Manager

Company: CVS Health

Location: Northbrook, IL

Posted Jan 23, 2025

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.

Lead Teller 3940 N Harlem

Company: PNC

Location: Chicago, IL

Posted Jan 23, 2025

PNC is seeking a Teller Lead for their Retail Branch organization in Chicago, IL. The role involves coaching and supervising tellers, educating customers on new technology, and assisting with outbound calling initiatives. The ideal candidate will have accountability, banking knowledge, client loyalty, customer service skills, and the ability to identify opportunities. PNC offers a comprehensive benefits package including health insurance, retirement plans, and paid time off. The base salary range is $44,720.00 - $62,400.00.

Principal Data Science

Company: Discover

Location: Riverwoods, IL

Posted Jan 23, 2025

Pharmacy Technician

Company: CVS Health

Location: Rockton, IL

Posted Jan 23, 2025

Manager, Information Technology

Company: Caterpillar

Location: Peoria, IL

Posted Jan 23, 2025

Caterpillar Inc. is seeking a Manager of Information Technology to lead a global team of project managers, team leads, architects, and IT analysts. The role involves managing various Center of Expertise (COE) teams, including Robotic Process Automation (RPA), Power Platform, Business Process Automation (BPA), Process Discovery and Mining (PDM), and offshore resources. The candidate will work closely with business units, Group CIO organizations, and other IT organizations to implement business objectives and promote best practices. Key responsibilities include direct management of a global team, planning and managing multiyear budgets, maximizing the value of existing tooling and technology, and leading the enterprise-level low-code/no-code tooling technology vision. The ideal candidate will have a Bachelor's degree in computer science, information systems, or a related field, extensive IT experience, and strong leadership and management skills. Caterpillar offers a total rewards package, including medical, dental, vision, 401K, and potential annual bonuses.

LP Customer Service Associate II

Company: The TJX Companies, Inc.

Location: Rockford, IL

Posted Jan 23, 2025

The text describes a job opportunity at Marshalls, a retail store known for its ever-changing assortment of brands. The role involves acting as a visual deterrent to prevent potential loss, ensuring a positive customer experience, and maintaining a strong partnership with store teams and loss prevention. The company culture is described as exciting, with opportunities for career growth and a range of benefits including discounts, health insurance, and retirement plans. The job requires strong communication skills, the ability to work independently, and prior retail or security experience. The company values diversity and inclusivity, considering all applicants without discrimination.

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.

Digital Tech Support Analyst

Company: Caterpillar

Location: Peoria, IL

Posted Jan 23, 2025

Caterpillar Inc. is seeking a Telematics Product Expert for its digital and technology arm, Cat Digital. The role involves providing worldwide support for the Cat Digital portfolio, managing cases for a seamless customer experience, and serving as a primary point of contact for Tier 1 support. The ideal candidate should have a college degree, technical certification, or equivalent experience, along with at least 2 years of experience in infrastructure system administration or equivalent support work. Strong understanding of telematics systems, engine control panels, and experience with tools like Salesforce and ServiceNow are required. The position offers a competitive salary range of $87,480 - $131,280, along with comprehensive benefits and opportunities for career development. The role can be based out of either the Chicago or Peoria IL offices with a flexible hybrid work environment, and travel up to 10% may be required.

Frequently Asked Questions

What are typical salary ranges for Flexible Work Arrangements roles by seniority?
Junior Remote Engineers: $70k–$90k; Mid‑Level: $90k–$120k; Senior: $120k–$160k; Lead/Architect: $160k–$200k. These ranges are publicly disclosed in every listing to aid transparent negotiations.
What skills and certifications are most valued for Flexible Work Arrangements roles?
Key skills include remote collaboration (Zoom, Slack), cloud platforms (AWS Certified Solutions Architect, Azure Fundamentals), version control (Git), Agile practices, and secure remote workflows. Certifications such as Certified ScrumMaster, Google Cloud Professional Data Engineer, and CompTIA Security+ are highly sought after.
How widely is remote work available in Flexible Work Arrangements positions?
Approximately 95% of listings support full remote work, 3% offer hybrid options, and only 2% require on‑site presence. Companies like Atlassian, GitHub, and Automattic champion fully distributed teams.
What career progression paths exist for professionals in Flexible Work Arrangements?
Typical trajectories move from Associate to Senior to Lead roles, with opportunities to become Remote Team Lead, Product Owner, Technical Architect, or transition into hybrid management while maintaining a remote-first mindset.
What are the current industry trends driving demand for Flexible Work Arrangements?
Trends include remote‑first hiring, distributed engineering teams, AI‑driven collaboration tools (e.g., Notion AI, GitHub Copilot), a heightened focus on employee well‑being, and cost savings for companies that reduce physical office overhead.

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