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.

AI Platform Engineer (GCP) - Remote

Company: The Hartford

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor's degree in Computer Science, Computer Engineering, or a technical field. Manage engineering tasks, driving execution, and optimizing workflows with…

Trade Show Security Officer

Company: United Security Services

Location: Chicago, IL

Posted Jul 07, 2025

Act to enforce client & facility regulations and directives for the site pertaining to exhibitors, guests, organizers personnel, visitors, and premises.

Data Scientist (Hybrid)

Company: Enova International

Location: Chicago, IL

Posted Jul 07, 2025

At times, you may be asked to conduct ad hoc analysis using statistical and financial tools to recommend for risk management, marketing and operational…

2nd Shift CNC Machinist

Company: OPW

Location: Skokie, IL

Posted Jul 07, 2025

Benefits: Our total rewards package for eligible team members also includes: a 401(k) savings plan with employer contributions; medical, dental and vision…

Senior Brand Manager - Cottonelle® Flushable Wipes

Company: Kimberly-Clark

Location: Chicago, IL

Posted Jul 06, 2025

Diverse income protection insurance options to protect yourself and your family in case of illness, injury, or other unexpected events. In this role, you will:

HVAC Service Technician

Company: Aire Serv

Location: Bedford Park, IL

Posted Jul 05, 2025

Valid driver's license and clean driving record. We employ a front-line service system that, when followed, will consistently generate 5-star reviews.

Retail Sales Associate

Company: The Hireverse

Location: Rosemont, IL

Posted Jul 07, 2025

As a *Retail Sales Associate*, you will play a key role in driving sales and providing outstanding customer service.

HVAC Service Technician

Company: Guardian Heating & Cooling Services LLC

Location: Chicago, IL

Posted Jul 07, 2025

Valid driver's license and insurable driving record. Service / maintenance / repair on residential heating and air conditioning systems.

Permanent Substitute Teacher

Company: Oak Park Elementary School District 97

Location: Oak Park, IL

Posted Jul 06, 2025

They establish a positive rapport with students, motivating them to develop the skills, attitudes, and knowledge needed to pursue their full potential.

Controller/Accountant Automotive Dealership

Company: Confidential Car Dealership

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor's degree in Accounting, Finance, or related field; CPA or CMA preferred. Manage the financial planning and analysis process, including forecasting,…

Controller

Company: Housing Opportunity Development Corporation

Location: Skokie, IL

Posted Jul 07, 2025

Daily: Oversee invoice processing, check deposits, data entry, account reconciliation, and records filing. Education: Bachelor’s degree in finance, accounting,…

Project Manager

Company: Michael Page

Location: Chicago, IL

Posted Jul 06, 2025

The Project Manager is responsible for scheduling, oversight of construction and communication with project team. Bonus per project (up to 12%).

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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