Flexible Schedule Jobs in Chicago, IL

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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.

Cat Digital/Cat Technology - Software Engineer

Company: Caterpillar

Location: Chicago, IL

Posted Sep 09, 2025

Software Product Technical Knowledge: knowledge of technical aspects of a software product; ability to design, configure and integrate technical aspects of…

Dispatch Solutions Representative

Company: ACCEL ENTERTAINMENT

Location: Burr Ridge, IL

Posted Sep 09, 2025

Dispatch service calls to Amusement Technicians to address and/or resolve technical customer issues in the field. $19-$22 plus night shift differential pay.

Registered Client Service Associate

Company: FourStar Wealth Advisors, LLC

Location: Chicago, IL

Posted Sep 10, 2025

Required licensing: FINRA 65 or 66; will consider other FINRA licensing. Excellent skills in Microsoft Office Suite and other technologies.

Cat Digital/Cat Technology – Data Scientist/Technical Analyst

Company: Caterpillar

Location: Chicago, IL

Posted Sep 09, 2025

Bachelor’s degree or higher in data science, computer engineering, electrical engineering or related degree (selected candidates must complete their degree by…

Project Manager

Company: Chanen Construction Co.

Location: Downers Grove, IL

Posted Sep 09, 2025

Minimum of five years’ experience in project management including but not limited to dealing with owners and engineers, clients, employees, agency personnel,…

Special Education Teacher

Company: Parkland Preparatory Academy

Location: Morton Grove, IL

Posted Sep 10, 2025

Parkland Preparatory Academy, one of Chicago's most innovative and dynamic therapeutic day schools, is seeking Special Education teachers with LBS-1…

Exhibitor Services Representative

Company: SourceOne Events

Location: Elmhurst, IL

Posted Sep 10, 2025

This individual with ensure exceptional customer satisfaction, possess strong organizational skills and play a crucial role in driving future business while and…

Digital Advertising Designer

Company: Accelerated Digital Media

Location: Chicago, IL

Posted Sep 11, 2025

This includes graphic design, animated gifs, and motion design for paid channels (such as Meta, TikTok, Pinterest, YouTube, LinkedIn, and Display).

Project Manager - JOC

Company: F.H. Paschen

Location: Chicago, IL

Posted Sep 10, 2025

Knowledge of construction, design, cost reporting and cash flow management. Develop field quality assurance and quality control plan with Superintendent.

Graphic Designer

Company: Ghafari

Location: Chicago, IL

Posted Sep 11, 2025

Education: Bachelor’s degree in graphic design, marketing, or related field. Generate content ideas and develop posts for social media.

Staff Accountant

Company: Third Road Management LLC

Location: Glen Ellyn, IL

Posted Sep 11, 2025

Prepare and review various multi-state sales tax filings. Perform filing or other duties as requested by client. Facilitate cash management as needed.

Dispatch/Customer Service

Company: Banner Personnel Service, Inc.

Location: Chicago, IL

Posted Sep 10, 2025

Perform high-volume data entry with a strong emphasis on accuracy, including logging completed paybox repairs across multiple systems.

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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