Flexible Schedule Jobs in Chicago, IL

34,503 open positions · Updated daily

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

Project Manager, Locomotive

Company: Progress Rail

Location: La Grange, IL

Posted Aug 29, 2025

Develop and implement risk management strategies to minimize project risks. Measure project performance using established systems, tools, and techniques.

Technical Accounting Manager

Company: Creative Financial Staffing

Location: Des Plaines, IL

Posted Aug 30, 2025

Salary range based off experience level, 130k-145k plus bonus. Work cross-functionally with Division CFO's and operating companies’ management, as well as…

Senior Accountant

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Aug 30, 2025

Prepare reports to substantiate individual transactions prior to monthly close process. The Senior Accountant will compile and analyze financial information to…

Experienced Service Plumber

Company: FlowPro Plumbing

Location: Chicago, IL

Posted Aug 29, 2025

Valid driver's license and a clean driving record. Upon arrival, you greet clients with a smile, ready to inspect their plumbing systems, identify issues, and…

Flex Security Officer - Willis Tower - Chicago

Company: Titan Security

Location: Chicago, IL

Posted Aug 29, 2025

Able to acquire and maintain a valid Illinois Permanent Employee Registration Card (PERC), including state accredited training requirements.

Part-Time Janitor - South side of Chicago - Experience and transportation required

Company: TMP Janitorial

Location: Chicago, IL

Posted Aug 28, 2025

*Has their own transportation (non-negotiable)*. *Proven working experience as a cleaner, janitor, cleaner technician, or any other relevant experience related…

Part Time Sales Associate

Company: Lori's Shoes

Location: Chicago, IL

Posted Aug 28, 2025

Process transactions accurately and efficiently at the point of sale. Generous employee discount on shoes, clothing, and accessories.

SEC Reporting Manager

Company: Creative Financial Staffing

Location: Des Plaines, IL

Posted Aug 30, 2025

Salary range based off experience level, 130k-145k plus bonus. Work cross-functionally with Division CFO's and operating companies’ management, as well as…

Senior Accountant

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Aug 30, 2025

Prepare reports to substantiate individual transactions prior to monthly close process. The Senior Accountant will compile and analyze financial information to…

Growth Lead

Company: Snaplii

Location: Chicago, IL

Posted Aug 28, 2025

Proficiency with data analysis tools (e.g., Google Analytics, Mixpanel, Amplitude, Metabase), with experience in cohort analysis, retention modeling, and…

Sales Specialist

Company: Christofle Silver Inc.

Location: Chicago, IL

Posted Aug 29, 2025

Develop local and international client book with the ability to recruit and develop top clients, inclusive of interior designers, estate managers, corporations.

Cook/ Chef

Company: Clarendale of Addison

Location: Addison, IL

Posted Aug 29, 2025

Visit residents periodically to evaluate food service such as quality, quantity, temperature, and appearance; and conduct evaluations to make revisions in…

Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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