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.

Painter/Taper

Company: Pepper Construction

Location: Chicago, IL

Posted Jun 30, 2025

Finishing corners and angles, measuring, cutting and installing metal corner beads, filling joints, nail indentations, holes and cracks.

View Details Apply on SimplyHired

LBS1 Teacher (year round option, $1500 sign on bonus)

Company: LearnWell

Location: Forest Park, IL

Posted Jun 30, 2025

Additionally, you will monitor and adjust teaching strategies to ensure student success and maintain accurate attendance and session reports.

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full time

Nurse Practitioner

Company: Vascular & Interventional Specialists

Location: Chicago, Illinois

Posted Jun 29, 2025

View Details Apply on healthecareers.com

Registered Nurse (RN) / Licensed Practical Nurse (LPN)

Company: Elite Care Management

Location: Countryside, IL

Posted Jun 30, 2025

RN or LPN state license. TB Test Results - 2 step or chest x-ray within the last 12 months OR QuantiFERON gold blood work within the last 5 years.

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Service Plumber - NO ON CALL

Company: TR MILLER HEATING AND COOLING

Location: Tinley Park, IL

Posted Jun 30, 2025

Maintain a valid driver’s license and a clean driving record. Run on average 4-5 residential service calls daily. Short-Term and Long-Term Disability.

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Early Career Assistant Planning Project Manager

Company: WSP

Location: Chicago, IL

Posted Jun 29, 2025

Capable interpersonal and communication skills when interacting with others, expressing ideas effectively and professionally to a technical and non-technical…

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Customer Support Associate

Company: Drive Sally

Location: Chicago, IL

Posted Jun 30, 2025

Complete driver onboarding (pricing, contract execution, vehicle matching). In this role, you will meet with and handle service requests for our prospective and…

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Service Coordinator

Company: National Lift Truck

Location: Franklin Park, IL

Posted Jun 30, 2025

Answer phones – transfer calls and take messages accordingly. Open work orders for service calls according to procedure. Issue purchase orders for sublet labor.

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Grant Accounting Manager

Company: Jane Addams Resource Corporation

Location: Chicago, IL

Posted Jun 30, 2025

Bachelor’s degree in Accounting, Finance, or a related field preferred. Monitor compliance with applicable federal, state, and private grant regulations,…

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Technical Team Lead

Company: Velvetech

Location: Chicago, IL

Posted Jun 30, 2025

Future projects as highly loaded SaaS web-based services for automating business processes in the field of medicine, insurance, finance, energy, including…

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Registered Nurse, Immediate Care

Company: Loyola University Health System

Location: Burr Ridge, IL

Posted Jun 30, 2025

Triage - Handles nurse-directed telephone calls from patients and seeks appropriate input and direction from the physician or functions from signed protocols if…

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Machine Operator

Company: Closets By Design Chicago Downtown

Location: Chicago, IL

Posted Jun 30, 2025

Operate woodworking machinery and hand tools. Experience with woodworking equipment and hand tools is a plus. Paid holidays and paid time off.

View Details Apply on SimplyHired

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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