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.

Lead Carpenter Foreman (Union)

Company: Market Contracting Services, Inc.

Location: Chicago, IL

Posted Oct 09, 2025

Reliable transportation and valid driver’s license. Communicate effectively with project managers, contractors, and team members though email, Procore, and…

Assistant Community Manager

Company: Morguard Residential

Location: Chicago, IL

Posted Oct 09, 2025

Maintain positive working relationships with residents, vendors, and contractors. High School Diploma required bachelor’s or Associates degree is ideal.

Skilled Installer

Company: Five Star Bath Solutions of Wilmette

Location: Northbrook, IL

Posted Oct 09, 2025

Knowledge of construction tools, materials, and techniques used in bathroom renovations. Minimum of 3-5 years of experience in bathroom or home installation,…

CDL-A Driver - Home Daily

Company: Venture Transport

Location: Cicero, IL

Posted Oct 08, 2025

$2,500 unlimited driver referral bonus. At Venture Transport, you’re more than just a driver—you’re the backbone of our success. 9 months in the past 3 years.

Commercial HVAC Technician

Company: Thermaster Mechanical

Location: Lombard, IL

Posted Oct 09, 2025

Personal tools including basic hand tools, cordless drill, refrigerant gauges. Candidate must be physically fit and able to carry or lift tools & equipment up…

Class A Regional Driver

Company: Transportation Concepts, Inc. (TCI)

Location: Lemont, IL

Posted Oct 08, 2025

Can expect to average 2300 to 2800 miles per week. .75 cents per mile + .05 cents per diem per mile. Average Weekly Pay $1900 plus. 34 hour reset - at HOME!!!

HEALTH FACILITIES SURVEILLANCE NURSE

Company: State of Illinois

Location: Westchester, IL

Posted Oct 09, 2025

Requires appropriate, valid Driver's license. This individual will conduct surveys of facilities, including state licensure, federal certification and complaint…

Senior Tax Accountant - 2+ Yrs Paid Tax Experience Required

Company: Intuit

Location: Chicago, IL

Posted Oct 09, 2025

Interact with customers both in-person and through Intuit’s state-of-the-art video communication tools. Minimum of 2 years of paid experience filing 30 or more…

Registered Nurse (RN) - Per Diem Days

Company: Rush Specialty Hospital

Location: Chicago, IL

Posted Oct 08, 2025

Initial and ongoing systematic patient assessment. Interpret assessment/diagnostic data including labs and telemetry. Compensation: $56 per hour.

Furniture Sales Associate

Company: CORT

Location: Carol Stream, IL

Posted Oct 09, 2025

Help us drive traffic to the Outlet through social media and networking. You're social media savvy, or have experience with marketing.

4th Grade Teacher

Company: Minnie Miñoso-Chicago Public Schools

Location: Chicago, IL

Posted Oct 08, 2025

Observe and evaluate students' performance, behavior, social development, and physical health. POSITION OVERVIEW Responsible for instructing students in an…

Customer Service Representative

Company: Roto-Rooter Services Company

Location: Lombard, IL

Posted Oct 08, 2025

Data entry, including customer contact information and relevant details concerning their plumbing problems. Be a trusted informational resource for Roto-Rooter…

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.

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