Flexible Schedule Jobs in Chicago, IL

Positions 34,512 Updated daily

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

Executive Chef

Company: Parlor Pizza Bar

Location: Chicago, IL

Posted Oct 21, 2025

Responsible for the selection, training, and development of the personnel within the department; planning, assigning and directing work: appraising performance;…

Client Services Representative

Company: Vive! Therapeutic Massage LLC

Location: Park Ridge, IL

Posted Oct 21, 2025

Be friendly, empathetic and respectful to our guests. Help guests schedule appointments, both in person and on the phone.

Lead IT Compliance Analyst (remote)

Company: US Foods, Inc.

Location: Rosemont, IL

Posted Oct 20, 2025

Conduct assessments of technology systems and processes to identify areas of risk and develop remediation plans.

Track Laborer

Company: CPKC

Location: Bensenville, IL

Posted Oct 22, 2025

Driver’s license verification and driving history. As a member of the Engineering team, a Track Laborer in the railroad industry plays a vital role in the…

Graphic Designer, Part Time

Company: PAWS Chicago

Location: Chicago, IL

Posted Oct 21, 2025

Manual dexterity to operate standard office equipment (e.g., computer keyboard, mouse, telephone, copier, printer).

Full Stack Engineer

Company: Innovel Global Logistics

Location: Villa Park, IL

Posted Oct 20, 2025

High school diploma required; degree in Computer Science or related field preferred. You’ll be instrumental in developing internal tools, customer/vendor…

Copywriter

Company: Caterpillar

Location: Chicago, IL

Posted Oct 22, 2025

Degree in a relevant field and experience in a creative role within an agency or in-house corporate environment or equivalent working experience.

Janitor Chicago (Candidates with Disabilities Are ENCOURAGED To Apply)

Company: Ada S McKinley Community Services Inc

Location: Chicago, IL

Posted Oct 21, 2025

Requires 6 months experience in janitorial/custodial field (or completion of a janitorial/custodial- training program). Vacuums, shampoos and scrubs carpets.

Senior IT SOX Compliance Analyst

Company: Gallagher

Location: Rolling Meadows, IL

Posted Oct 21, 2025

Gallagher believes that all persons are entitled to equal employment opportunity and prohibits any form of discrimination by its managers, employees, vendors or…

Cybersecurity Analyst

Company: Alter Domus

Location: Chicago, IL

Posted Oct 21, 2025

Familiarity with malware analysis, reverse engineering, and forensic tools. Monitor security information and event management (SIEM) systems, intrusion…

Technical Product Owner / Software Development Expert

Company: Emergent Software

Location: Chicago, IL

Posted Oct 21, 2025

Experience operating as the liaison between agile development teams and users in defining requirements, performing business analysis, and driving delivery in…

Service Specialist

Company: TSR Consulting Services, Inc (Confidential Client)

Location: Chicago, IL

Posted Oct 21, 2025

Act as first point of contact for all incoming employer-client & agent calls on the Service phone line. Must develop a broad working knowledge of company…

Frequently Asked Questions

What are typical salary ranges by seniority for flexible schedule tech roles?
Entry‑level (0‑2 years) $70k‑$95k; Mid‑level (2‑5 years) $95k‑$135k; Senior (5‑10 years) $135k‑$180k; Lead/Principal (10+ years) $180k‑$250k. These ranges adjust for region and industry, with remote‑first firms often offering cost‑of‑living adjustments.
What skills and certifications are required for flexible schedule positions?
Core skills: proficiency with Git, GitHub/GitLab, Slack, JIRA, Asana, and Zoom for asynchronous collaboration. Certifications: AWS Certified Solutions Architect, Google Cloud Professional Cloud Architect, Certified ScrumMaster (CSM), Project Management Professional (PMP), and Google UX Design Certificate are highly valued.
Is remote work available for flexible schedule roles?
Yes—most flexible schedule positions are fully remote. Companies such as GitLab, Automattic, and Atlassian provide 100% remote options, while others offer hybrid models with flexible days. Remote‑first culture is a standard expectation across this category.
What career progression paths exist in flexible schedule tech roles?
Typical paths: Junior Engineer → Mid‑level Engineer → Senior Engineer → Staff Engineer → Principal Engineer or Product Manager → Senior PM → Lead PM → Head of Product. Continuous learning, mentorship, and internal promotion are key, with many firms investing in skill development and certifications.
What industry trends are shaping flexible schedule jobs?
Key trends include the rise of remote‑first companies, AI‑powered collaboration tools like Notion AI and Slack GPT, increased demand for asynchronous communication expertise, higher adoption of flexible work policies in Fortune 500 firms, and a growing freelance economy for hourly remote specialists.

Related Pages

© 2026 Job Transparency. All rights reserved.