Flexible Schedules Jobs in Chicago, IL

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

Cook I

Company: Sodexo

Location: Freeport, IL

Posted Jan 23, 2025

Shift Supervisor Trainee

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health is offering a Shift Supervisor Trainee position, an entry-level role designed to prepare employees for higher-level supervisory roles. The role involves working effectively with store management and crews, supervising activities, and ensuring smooth store operations. The company emphasizes a human-centric approach to healthcare, focusing on personal, convenient, and affordable solutions. Upon successful completion of the training, trainees can be considered for Operations Supervisor or Shift Supervisor positions. The role requires deductive reasoning, analytical skills, and computer skills, with a flexible schedule including early mornings, overnight, and weekend shifts. The company offers a comprehensive benefits package, including medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and a CVS store discount.

Shift Supervisor Trainee

Company: CVS Health

Location: Springfield, IL

Posted Jan 23, 2025

CVS Health is offering a Shift Supervisor Trainee position, an entry-level role designed to prepare employees for higher-level supervisory roles. The role involves working effectively with store management and crews, supervising activities, and ensuring smooth store operations. The company emphasizes a human-centric approach to healthcare, focusing on personal, convenient, and affordable solutions. Successful trainees can be considered for Operations Supervisor or Shift Supervisor positions, which involve leading store staff, maintaining customer loyalty through excellent service, and handling all customer relations issues. The role requires deductive reasoning, analytical skills, computer skills, and advanced communication abilities. The pay range is $16.00 - $24.00, and the company offers comprehensive benefits including medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and PTO.

Target Security Specialist

Company: Target

Location: Oak Lawn, IL

Posted Jan 23, 2025

Senior Sustainability Associate - ESG

Company: ZS

Location: Chicago, IL

Posted Jan 23, 2025

Cook

Company: Sodexo

Location: Chicago, IL

Posted Jan 23, 2025

Sodexo is seeking a full-time Cook for their Gateway Alcohol & Drug Rehabilitation facility in West Chicago. The role involves preparing and serving nutritious dishes, reducing food waste, and providing excellent customer service. The job offers a pay range of $17.00 per hour, a flexible work environment, and comprehensive benefits including training, advancement opportunities, and a full array of health, wellness, and retirement benefits. Sodexo values diversity and inclusion, fostering an environment where all employees are respected and valued.

Auction Services Associate - Part Time

Company: CarMax

Location: Aurora, IL

Posted Jan 23, 2025

The Auction Services Associate at CarMax's Chicago Auction Center in Montgomery, Illinois, is responsible for maintaining inventory, vehicle preparation, receiving, scanning, reconciliation, and quality control. They ensure zone maintenance, security, and a clean work environment. The role involves multitasking in a fast-paced setting, participating in auction support, and delivering vehicles from off-site vendors. The associate also assists in training new staff, adheres to standardized work processes, and provides exceptional customer service. The job requires lifting up to 50 lbs, flexible work hours, and the ability to work in various conditions. CarMax offers competitive pay and benefits, including training, and is an Equal Opportunity Employer.

Frequently Asked Questions

What are typical salary ranges for flexible‑schedule tech roles by seniority?
Junior developers in flexible settings earn $60k–$90k, mid‑level engineers $90k–$140k, senior engineers $140k–$200k, and tech leads or product managers $160k–$250k, with variations based on location, stack, and remote cost adjustments.
Which skills and certifications are most valuable for flexible‑schedule positions?
Proficiency in Git, CI/CD pipelines, and cloud platforms (AWS, Azure, GCP) is essential. Remote collaboration tools like Slack, Zoom, and Jira are standard. Certifications such as AWS Certified Solutions Architect, Certified Scrum Master, or Google Cloud Professional Data Engineer boost credibility.
How common is remote work availability in flexible‑schedule roles?
Over 80% of the 1501 listings allow full remote work, with 15% offering hybrid models that require 1–2 on‑site days per month. Companies set core hours (e.g., 10 am–3 pm UTC+2) to synchronize cross‑time‑zone teams.
What career progression paths exist within flexible‑schedule tech teams?
Typical paths move from Junior Engineer to Senior Engineer, then to Technical Lead or Engineering Manager, and ultimately to VP of Engineering or CTO. Roles such as Product Owner, UX Lead, or Data Engineering Lead also offer vertical growth while maintaining schedule flexibility.
What industry trends are shaping the future of flexible schedules?
The industry is moving toward AI‑driven scheduling tools that auto‑align meetings with optimal personal productivity windows. Companies are adopting outcome‑based performance metrics instead of fixed hours, and the demand for mental‑health‑friendly work hours is rising across all tech sectors.

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