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.

General Construction Worker/Project Manager

Company: Archetype Homes, Inc

Location: Chicago, IL

Posted Aug 17, 2025

Complete carpentry tasks as directed, including rough framing, finish carpentry (trim), door hanging, window installation, deck building, cabinet installation,…

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INSURANCE SALES AGENT-TEAM MEMBER

Company: STATE FARM INSURANCE

Location: Chicago, IL

Posted Aug 17, 2025

Answer calls from insurance customers promptly and provide a high level of service. Network in various ways to develop new prospects.

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dental insurance health insurance health savings account

Physician Assistant - PA - Palliative Care

Company: Endeavor Health

Location: Naperville, Elmhurst, Plainfield, IL

Posted Aug 17, 2025

View Details Apply on healthecareers.com

Data Scientist

Company: Deloitte

Location: Chicago, IL

Posted Aug 17, 2025

Undergraduate degree in a quantitative field (computer science, engineering, mathematics, physics, machine learning, statistics).

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Housekeeping / Janitor Supervisor – Part-Time Hourly

Company: Villa Dubois Guest House

Location: Chicago, IL

Posted Aug 16, 2025

Clean guest rooms and common areas to a high standard. *Must have housekeeping/janitorial experience in hotels, Airbnb, or vacation rentals within the last 5…

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Truck Driver CDL A Daily

Company: Ryder

Location: Chicago, IL

Posted Aug 16, 2025

Ensuring compliance with applicable federal and/or state laws, regulations, and/or agency rules, standards and guidelines. Minimum 21 years of age.

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UNARMED Security Officer

Company: Gamma Team Security Inc

Location: Cicero, IL

Posted Aug 17, 2025

Valid registration as a security officer. Ability to operate surveillance equipment. Report on daily activities and any security incidents.

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Executive Chef

Company: Catering by Michaels

Location: Morton Grove, IL

Posted Aug 16, 2025

Strong knowledge of financial management disciplines to include but not limited to P&L, budget design and management, and financial analysis.

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Janitor (Union) - Logan Square

Company: HHDC

Location: Chicago, IL

Posted Aug 16, 2025

Ability to work with lawn machinery and power tools. Keeps up the exterior cleanliness and presentation of the property, including lawn care, window washing (…

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CNC Production/Machine Operator

Company: Hyperion Materials & Technologies

Location: Elk Grove Village, IL

Posted Aug 16, 2025

Basic computer competency (email, data entry into Material Mgmt. Proven independent performer that needs minimal supervision. Systems, log notes in MSWord).

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Insurance Agent Customer Service Rep/Team Member

Company: State Farm Insurance Chicago,Illinois

Location: Chicago, IL

Posted Aug 17, 2025

Be able to discover gaps in insurance customers' plans during calls, address gaps in coverage - Use a customer-focused, needs-based review process to educate…

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Senior Tax Associate IN OFFICE

Company: River East Tax and Accounting Services Inc

Location: Chicago, IL

Posted Aug 17, 2025

Identify and implement tax planning strategies to minimize clients’ tax liabilities. Analyze financial data to determine the appropriate tax treatment of…

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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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