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.

Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

All agents must be able to obtain licensing through the Illinois Department of Financial and Professional Regulation, are required to score a minimum of 95%…

Carwash Attendant/ Customer Service

Company: Graham Enterprise, Inc

Location: Oakbrook Terrace, IL

Posted Aug 09, 2025

Treat each customer as a guest. Perform visual inspections in the tunnel and back room to ensure all equipment and chemicals are functioning properly.

CDL-A Truck Driver - Temp-Controlled Freight - up to $1,650/week

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,365/week. *Home weekly* – typically for 48 hours.

Patient Care Contact Center Representative

Company: ACCESS Community Health Network

Location: Chicago, IL

Posted Aug 10, 2025

If personal vehicle is employed, a current driver’s license and proof of insurance is required. Return patient calls/messages and provide additional information…

School Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

Ensure the safety of staff and student. Ability to operate surveillance equipment. Report on daily activities and any security incidents.

CDL A Dry Van Truck Driver: Home Weekly

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

OFSAA Finance Data Analyst Sr

Company: Huntington Bank

Location: Chicago, IL

Posted Aug 09, 2025

The Senior Financial Analyst will examine data and variances, build out and enhance data management processes, develop KPI metrics and provide analysis that is…

Master Plumber

Company: Leaf Home

Location: Chicago, IL

Posted Aug 10, 2025

Train, coach and develop installation employees and contractors both in the office and in the field. Must hold a valid driver's license.

Manager, GenAI Engineer

Company: Deloitte

Location: Chicago, IL

Posted Aug 09, 2025

A bachelor's degree in computer science, software engineering, or a related discipline. The ideal candidate will be a dependable team player and mentor,…

Carpenter / Home Improvement Specialist

Company: Mr. Handyman

Location: Chicago Ridge, IL

Posted Aug 09, 2025

Own your own professional grade tools for a large variety of jobs. The pay range for this position is $32 to $36+/hr and is dependent on your experience as a…

Private Preschool Teacher

Company: TeacherCare

Location: Flossmoor, IL

Posted Aug 09, 2025

Clean driving record and comfortability driving children to and from actives. Background in early childhood education or related field is preferred; Montessori…

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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