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.

CDL-A Dedicated Truck Driver

Company: Marten Transport

Location: Chicago, IL

Posted Aug 19, 2025

Must have a minimum of 6 months recent qualified CDL-A driving experience to apply. Hazmat and tanker endorsement (or scheduled to obtain within 30 day window).

Project Manager - Multifamily Projects

Company: Michael Page

Location: Chicago, IL

Posted Aug 19, 2025

Ability to hire, train, develop and manage a team of Project Managers by providing intentional and proactive leadership. Travel to job site 1-2 days a week.

Product Analyst

Company: CI Financial Corp.

Location: Chicago, IL

Posted Aug 19, 2025

Demonstrated expertise and certifications in Salesforce or willingness to obtain administrator/consultative certification within 90 days.

Registered Nurse

Company: Oak Street Health

Location: Oak Park, IL

Posted Aug 19, 2025

Active Registered Nurse (RN) Licensure in good standing with the applicable state. Qualified applicants with arrest or conviction records will be considered for…

CDL-A Dedicated Truck Driver

Company: Marten Transport

Location: Stickney, IL

Posted Aug 19, 2025

Must have a minimum of 6 months recent qualified CDL-A driving experience to apply. Hazmat and tanker endorsement (or scheduled to obtain within 30 day window).

Remote Teacher

Company: Tutor Me Education

Location: Chicago, IL

Posted Aug 19, 2025

Previous tutoring/teaching experience highly preferred. Ability to make learning fun and interactive, with the focus of the tutoring often determined by student…

Mid-Market Solutions Engineer

Company: Flock Safety

Location: Chicago, IL

Posted Aug 19, 2025

Engineers may find themselves in coding interviews or architecture discussions, sales roles may present mock discovery calls, and leadership roles may craft 90…

CDL-A Dedicated Truck Driver

Company: Marten Transport

Location: Berwyn, IL

Posted Aug 19, 2025

Must have a minimum of 6 months recent qualified CDL-A driving experience to apply. Hazmat and tanker endorsement (or scheduled to obtain within 30 day window).

Extrusion Process Technician-Nights

Company: Pactiv Evergreen

Location: Bedford Park, IL

Posted Aug 19, 2025

Two or four year technical degree or certification. Good understanding of mechanical and electrical principles and applications. 3-day weekend every other week.

Truck Driver

Company: Atlas Toyota Material Handling, LLC

Location: Bedford Park, IL

Posted Aug 19, 2025

Hold a valid CDL-A license with a clean driving record. Experience and certification in the operation of forklifts and aerial lift equipment.

Retail Media Strategy Lead

Company: Kimberly-Clark

Location: Chicago, IL

Posted Aug 19, 2025

Responsible for paid search (and associated optimizations) across retailers by brand, leveraging analytic tools to maximize Retail Search performance across…

Special Education Teacher- Therapeutic Day School Autism

Company: Soaring Eagle Academy

Location: Lombard, IL

Posted Aug 19, 2025

Supervision/mentoring by a DIR® Trainer with extensive experience in autism, curriculum development/implementation, developmental language model and DIR®…

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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