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.

Independent Sales Associate

Company: United Roofing & General Contractors

Location: Chicago, IL

Posted Jul 15, 2025

Generate and manage leads through field prospecting, referrals, and company-provided sources. Are you ready to take control of your income, grow your career,…

Customer Experience Video Scout (Travel Required)

Company: Reality Based Group

Location: Chicago, IL

Posted Jul 16, 2025

Valid driver's license and a reliable form of transportation. Comfort and enjoyment with extended travel and independent work.

BAS Project Manager - Applied Controls

Company: Air Comfort

Location: Broadview, IL

Posted Jul 16, 2025

Proactively communicate with field personnel regarding status of work and expected costs. This position will work closely with all employees of Applied Controls…

Sales Assistant - Large Retail Customers

Company: MACVAD USA

Location: Lincolnwood, IL

Posted Jul 15, 2025

A full driver’s license is required. Data entry, file management and reporting as required. Full-time, permanent role with a global company.

HVAC Master Technician/Technical Trainer

Company: Leslie Heating & Cooling

Location: Lombard, IL

Posted Jul 16, 2025

Provide field support and advanced troubleshooting for complex service or turnover calls. Run service calls (on demand). $85,000 – $125,000 per year*.

Entry Level Customer Service Representative - Weekly Pay

Company: Tri-State Energy Group

Location: Forest Park, IL

Posted Jul 16, 2025

We offer incredible advancement and management training from entry-level to senior-level positions. Prior knowledge and experience in customer service account…

Graphic Designer – Wayfinding & Compliance

Company: Stratus

Location: Elmhurst, IL

Posted Jul 16, 2025

Our work transforms environments through strategic design, high-impact visuals, and precise production. Bachelor’s degree in Graphic Design, Environmental…

RN (Registered Nurse) Pediatric Private duty

Company: Kingsway Home Health

Location: Chicago, IL

Posted Jul 15, 2025

Requirements\*\*minimum of 1-year experience as LPN/RN\*\*\*\* must be licensed in the state of Illinois\*\*\*\*CPR card, Driver’s license, S.

Marketplace Digital Marketing Manager

Company: State of Illinois

Location: Chicago, IL

Posted Jul 15, 2025

The Department of Insurance (DOI) regulates the insurance market in the State of Illinois including, but not limited to, licensing and educating insurance…

Financial Systems Reporting and Data Senior Analyst

Company: Plante Moran

Location: Chicago, IL

Posted Jul 16, 2025

Compensation is commensurate with technical skills and experience is provided in accordance with applicable state requirement.

Customer Experience Representative - ICS

Company: J.B. Hunt

Location: Chicago, IL

Posted Jul 15, 2025

This position will exemplify a customer-centric spirit to develop and maintain excellent customer relationships as well as maximize business potential.

Sr Analyst, Incident Response

Company: PayPal

Location: Chicago, IL

Posted Jul 16, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

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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