Flexible Work Schedules Jobs in Chicago, IL

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Looking for Flexible Work Schedules jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Schedules position in the Chicago, IL area.

CDL-A Truck Driver - 1099 - Up to $5,000 / week

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. No credit check, $0 down. Balloon payment at end of term. Earn 70% of line haul.

Marketing Director - Personal Injury experience

Company: Zentech Consulting

Location: Chicago, IL

Posted Aug 06, 2025

Identify and develop new business opportunities within the legal industry. Your ability to understand what drives consumer decisions and translate that into…

Associate Graphic Design

Company: AmTab Manufacturing

Location: Bensenville, IL

Posted Aug 06, 2025

As a minority-owned, 100% made-in-the-USA company, AmTab is proud to own our design, manufacturing, and installation process from start to finish.*.

Senior Manager, Software Engineering, Back End (Java, Node, AWS)

Company: Capital One

Location: Chicago, IL

Posted Aug 06, 2025

That includes everything from credit assessment and terms decisioning, to invoicing and payment processing, to servicing, collections and cash application.

Senior Industrial Hygiene Project Manager

Company: Specialty Consulting Inc.

Location: Chicago, IL

Posted Aug 06, 2025

This is a hands-on position with 50% of time spent in the field, where you will be conducting field inspections for hazardous materials and provide oversight…

CDL-A Truck Driver: Company or 1099

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. *Top drivers earn up to $90,000 per year*. No credit check, $0 down. Balloon payment at end of term.

HVAC Technician

Company: JLL

Location: Chicago, IL

Posted Aug 06, 2025

A stationary engineer license is a must. When assigned to install new/used equipment, must be able to operate appropriate construction tools and equipment.

IT Product Manager

Company: Charles Schwab

Location: Chicago, IL

Posted Aug 06, 2025

Familiarity with social media, web design, and advanced trading applications; proficient in Excel and PowerPoint. User acceptance testing prior to releases.

Senior Security Governance, Risk & Compliance (GRC) Analyst

Company: Boeing

Location: Chicago, IL

Posted Aug 06, 2025

This role focuses on configuration, administration, and ongoing support to ensure effective cybersecurity risk visibility and reporting striving for highest…

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted Aug 06, 2025

Collaborate with and across Agile teams to design, develop, test, implement, and support technical solutions in full-stack development tools and technologies.

Tool Room Machinist 1st shift)

Company: Klein Tools

Location: Elk Grove Village, IL

Posted Aug 06, 2025

Fits and assembles parts into complete assembly, using jigs, fixtures, surface plates, surface table, hand tools and power tools. Ability to weld is a plus.

Frequently Asked Questions

What are the typical salary ranges for Flexible Work Schedules roles at different seniority levels?
Entry‑level remote software engineers earn between $70,000 and $90,000 annually. Mid‑level roles (2‑5 years) range from $90,000 to $120,000. Senior engineers with 5‑10 years of experience command $120,000 to $160,000. Lead or management positions typically fetch $160,000 to $200,000, with an additional 5‑10% remote work premium.
Which skills and certifications are most valuable for professionals seeking Flexible Work Schedules roles?
Candidates should master Agile/Scrum methodology, hold certifications such as Certified ScrumMaster (CSM) or Project Management Professional (PMP), and be proficient with collaboration tools like Slack, Microsoft Teams, and Jira. Knowledge of cloud platforms (AWS, Azure, GCP) and remote security practices adds significant value.
How common is remote work availability in Flexible Work Schedules positions?
Over 90% of listings in this category specify full‑remote or hybrid options. Typical arrangements include 3‑5 remote days per week, with optional in‑office hubs for collaboration or onboarding.
What career progression paths exist for professionals in Flexible Work Schedules roles?
A typical path starts as a Remote Junior Engineer or Coordinator, advances to Senior Engineer or Product Owner, then to Lead or Manager roles, and eventually to Director or VP positions overseeing distributed teams.
What industry trends are shaping Flexible Work Schedules?
The shift to flexible schedules is driven by a 25% increase in remote hiring post‑pandemic, adoption of AI‑powered scheduling tools, and a growing emphasis on pay transparency to attract diverse talent.

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