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.

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Emergency Medicine - Full Time - Chicago, IL

Company: Advocate Health

Location: Chicago, Illinois

Posted Jul 20, 2025

View Details Apply on healthecareers.com

AI and Data Engineer

Company: Sentinel Technologies, Inc.

Location: Chicago, IL

Posted Jul 21, 2025

The AI and Data Engineer will design and build scalable data pipelines, develop AI-powered applications and services (primarily in Python), and contribute to…

View Details Apply on SimplyHired

Janitorial

Company: HELPING HANDS CLEANING SERVICE

Location: Elmhurst, IL

Posted Jul 21, 2025

Restock supplies in bathrooms, break rooms, and common areas. Monitor and report any necessary repairs or replacements. Proficiency in English is required.

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Retail Security Officers $18.50/Hr

Company: Per Mar Security Services

Location: Chicago, IL

Posted Jul 21, 2025

The selected individual will patrol and secure assigned premises as well as identify risks to staff and patrons.

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Business Data Analyst

Company: UTLX Full Service

Location: Chicago, IL

Posted Jul 21, 2025

Bachelor’s degree in Data Analytics, Business Analytics, Statistics, Computer Science, or a related field is required. Data analytics: 3 years (Required).

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Accountant, Real Estate and Workplace Services

Company: Google

Location: Chicago, IL

Posted Jul 21, 2025

The gRRR (Google REWS, Reporting & RCS) team helps to develop and support new processes and business relationships with a variety of cross-functional…

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Maintenance

Company: Chicago Commons Association

Location: Chicago, IL

Posted Jul 21, 2025

Remove trash daily from classrooms, offices, meeting rooms, kitchen, restrooms, indoor play areas, and outdoor playgrounds.

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Supervisor, Environmental Services

Company: Loyola University Health System

Location: Maywood, IL

Posted Jul 21, 2025

Certification reimbursement (up to 1 certification). Demonstrates knowledge operating mechanical floor cleaners such as vacuums, scrubbers, and burnishers.

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REGISTERED NURSES (RN) Evening shift

Company: Austin Oasis

Location: Chicago, IL

Posted Jul 21, 2025

Current, unencumbered state license to practice as a Registered Nurse. Will direct the day-to-day functions of the nursing assistants in accordance with current…

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Join Our Team of Excellence: Full-Time Endocrinologist Opportunity

Company: Mercyhealth

Location: Rockford IL, and Janesville, WI

Posted Jul 21, 2025

View Details Apply on healthecareers.com

Software Test Engineer

Company: Caterpillar

Location: Chicago, IL

Posted Jul 20, 2025

Additionally, the applicant must have employment experience with: (1) Full stack SDET QA (Front end, API & Non- Functional testing); (2) Test automation…

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Product Specialist

Company: Manufacturer Company

Location: Bensenville, IL

Posted Jul 21, 2025

Check incoming orders for accuracy, answering phones, inputting customer data, processing orders, record keeping, email maintenance and other office duties.

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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