Flexible Work Schedule Jobs in Chicago, IL

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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.

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.

Construction Management, Project Manager -- Superintendent, Chicago

Company: Bushman Construction Management

Location: Chicago, IL

Posted Aug 10, 2025

0-5+years field experience in commercial construction. Chicago, IL 60630is a general contractor providing complete commercial construction and construction…

CDL-A Truck Driver - Temp-Controlled Freight - up to $1,650/week

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 $1,365/week. *Home weekly* – typically for 48 hours.

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.

Program Manager, Data Centers

Company: JLL

Location: Chicago, IL

Posted Aug 11, 2025

Working collaboratively with various stakeholders, you'll ensure successful program execution while proactively addressing risks and driving operational…

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,…

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…

Midmarket Software Sales - Founding Team Member for AI Startup

Company: Nestbox AI

Location: Chicago, IL

Posted Aug 10, 2025

*Founder-Level Impact:* You’ll be the first sales hire, working directly with our technical founders to shape GTM strategy, refine our offering for midmarket…

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.

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