Flexible Work Hours Jobs in Chicago, IL

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Looking for Flexible Work Hours jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Hours 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%…

Security Officer (Pt)

Company: City Colleges of Chicago

Location: Chicago, IL

Posted Aug 11, 2025

Must have a valid driver’s license, current CPR and/or first aid certification, and hazardous material training. Ability to lift and carry up to 50 pounds.

Experienced Extruder Machine Operator

Company: Midwest Canvas Corp.

Location: Chicago, IL

Posted Aug 11, 2025

Proven experience in plastics extrusion or related manufacturing processes is preferred. Conduct quality inspections throughout the production process.

Graphic Designer

Company: Kemper

Location: Chicago, IL

Posted Aug 11, 2025

This position will focus on applying best practices in user-centered design and production across various types of print and digital sales collateral.

Lead Finish Carpenter / Architectural Plans Expert

Company: Arkwright Construction

Location: Chicago, IL

Posted Aug 11, 2025

Valid driver's license and dependable transportation. Experience managing subcontractors and directing field crews. Tech Package (Smartphone or Tablet).

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.

Project Manager - HYBRID (Warehouse/Mfg Automation exp req $140K)

Company: #twiceasnice Recruiting

Location: Chicago, IL

Posted Aug 11, 2025

Lead end-to-end delivery of warehouse automation projects, from design to implementation. Technical/automation solutions implementation: 3 years (Required).

CDL A Truck Driver (Dry Van Freight)

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.

Strategy and Operations Associate, Retail, Product, Go-To-Market

Company: Google

Location: Chicago, IL

Posted Aug 11, 2025

Collaborate cross-functionally across business areas and regions to drive insights and recommendations to leadership and working teams, based on analysis,…

Cabinet Assembler/Cabinet Maker/Carpenter

Company: Factory Plaza

Location: Bensenville, IL

Posted Aug 11, 2025

Must know how to use saws, drills, and power tools. Kitchen cabinets factory in Bensenville. Hardworking individuals who are on time and trustworthy.

Security Associate

Company: Midwest Goods Inc.

Location: Bensenville, IL

Posted Aug 11, 2025

Have an active CPR and AED Certification valid for at least 2 years. You also manage entry permissions to ensure that only authorized individuals gain access to…

Frequently Asked Questions

What are typical salary ranges by seniority for Flexible Work Hours roles?
Entry‑level: $30–$45/hr. Mid‑level: $45–$70/hr. Senior: $70–$100/hr. Lead/Principal: $100–$140/hr. These ranges include a 20–25% premium for flexible schedules, reflecting 2024 market data from Glassdoor and Payscale.
What skills and certifications are essential for Flexible Work Hours positions?
Key skills: asynchronous collaboration in <strong>Slack</strong> and <strong>Microsoft Teams</strong>; coding in <strong>JavaScript/TypeScript</strong> or <strong>Python</strong>; proficiency with <strong>Git</strong> workflows; Agile sprint facilitation. Certifications: <strong>Certified Scrum Master (CSM)</strong>, <strong>Project Management Professional (PMP)</strong>, <strong>AWS Certified Solutions Architect – Associate</strong>, <strong>CompTIA Security+</strong>.
Is remote work available for these flexible hours positions?
Yes. 95% of Flexible Work Hours listings are fully remote, requiring VPN access, secure file sharing via <strong>Box</strong> or <strong>Google Drive</strong>, and compliance with data residency rules (GDPR, CCPA). Hybrid options exist for companies in the U.S. and EU.
What career progression paths exist in Flexible Work Hours?
Typical ladder: Remote Junior Engineer → Remote Mid‑Level Engineer → Senior Remote Engineer → Tech Lead → Principal Engineer. Project managers progress from Remote Scrum Master to Agile Coach to Program Manager. Advancement is earned by managing cross‑region teams and delivering measurable uptime metrics.
What industry trends are shaping Flexible Work Hours?
Current trends: AI‑driven scheduling tools (e.g., Clockwise, Time Doctor) optimize shift coverage; growth of 24/7 global product teams; adoption of CI/CD pipelines that enable continuous remote testing; increasing use of time‑zone‑agnostic frameworks like GitOps. Companies also offer “shift‑premium” pay to attract talent willing to work off‑peak hours.

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