Flexible Schedules Jobs in Chicago, IL

27,633 open positions · Updated daily

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.

Operations Manager

Company: CVS Health

Location: South Elgin, IL

Posted Jan 22, 2025

CVS Health is seeking an Operations Manager to lead a store team, driving execution and performance while enhancing customer service. The role involves overall store management, sales and inventory management, employee staffing and development, and financial management. The ideal candidate will have strong leadership, communication, and analytical skills, and be able to work flexible hours. CVS Health offers competitive pay, comprehensive benefits, and opportunities for professional growth.

Sr Customer Success Consultant

Company: TransUnion

Location: Chicago, IL

Posted Jan 22, 2025

TransUnion is seeking a Senior Customer Success Consultant with a Bachelor's degree in business, finance, or computer science, and 5+ years of experience in consultancy, project management, implementation management, and/or fraud management. The role involves working with great people, pioneering products, and cutting-edge technology. The consultant will lead customer engagements across various industries, providing best-in-class insights and deliverables. They will own the operational relationship with high-level clients, positioning themselves as trusted advisors. The role is hybrid, involving regular virtual and in-person work at an assigned TransUnion office location. Benefits include flexible time off, health benefits, parental leave, tuition reimbursement, and more. The U.S. base salary range for this position is $82,700.00 - $120,000.00 annually.

Financial Advisor - Career Change Opportunity

Company: Edward Jones

Location: Peoria, IL

Posted Jan 22, 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 overseeing branch processes. 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.

Pharmacy Technician

Company: CVS Health

Location: Aurora, IL

Posted Jan 22, 2025

Financial Advisor - Career Change Opportunity

Company: Edward Jones

Location: Peoria, IL

Posted Jan 22, 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 overseeing branch processes. 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.

Director Security Solutions Sales

Company: Mastercard

Location: Chicago, IL

Posted Jan 22, 2025

Mastercard is seeking a Director of Sales for the North American Services Team. The role involves leading a portfolio of key accounts, developing sales strategies, and driving revenue growth. The ideal candidate should have extensive experience in sales, particularly in the banking industry, and a deep understanding of cybersecurity trends. They must possess excellent relationship management skills, sales performance analysis capabilities, and a track record of quota achievement. The position offers a competitive salary range of $139,000 - $222,000 along with comprehensive benefits.

Retail Sales Associate

Company: Staples

Location: Rock Island, IL

Posted Jan 22, 2025

Operations Supervisor - Overnight

Company: Kohl's

Location: Ottawa, IL

Posted Jan 22, 2025

The role of a Supervisor in a Distribution Center involves managing day-to-day operations, ensuring inventory integrity, aligning with business partners, and maintaining a safe work environment. Key responsibilities include managing workflow, developing accuracy standards, ensuring dynamic staffing, and leading direct reports to achieve unit goals. The ideal candidate should have prior experience managing teams in a distribution warehouse, strong interpersonal communication skills, and a flexible work schedule. Preferred skills include experience with Operations and Operational Support Systems, automated MHE, and SQL.

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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