Flexible Work Schedule Jobs in Chicago, IL

75,597 open positions · Updated daily

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

C# Engineer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

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.

Global Practice Architect, Infrastructure III, Google Cloud

Company: Google

Location: Chicago, IL

Posted Aug 06, 2025

You will orchestrate across numerous contributing teams including solutions, services, partners, product engineering, marketing, and GTM stakeholder…

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.

Senior Consultant 1, Analytics, Insights, Report, A&T - DA Analytics

Company: Deloitte

Location: Chicago, IL

Posted Aug 06, 2025

Supervise day to day operations, set up processes for delivery including technical/functional documentation, scope of work, resource planning, design,…

Python Developer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

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…

Project Manager II

Company: Gilbane Building Company

Location: Chicago, IL

Posted Aug 06, 2025

Participates in enrollment for insurance and bonds; tracks and obtains trade contractors’ compliance. Strong technical and communication skills are critical.

Dump Truck Driver

Company: Hana Transport Inc.

Location: Chicago, IL

Posted Aug 06, 2025

Valid commercial driver's license (CDL A) with, 3+ years experience in dump/must have a clean CDL License with no more than 2 tickets in the past 3-years.

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 typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

Related Pages