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.

Assistant Project Manager - Light Industrial

Company: Michael Page

Location: Chicago, IL

Posted Oct 01, 2025

Review project implementation and gather data on project execution. Technical background with understanding of building engineering and commercial projects;…

Chef Manager

Company: Belmont Village Oak Park

Location: Oak Park, IL

Posted Oct 01, 2025

You will select, train and grow culinary talent within our state-of-the-art kitchen and develop lasting relationships with residents and guests in our…

Tax Accountant - 2+ Yrs Paid Tax Experience Required

Company: Intuit

Location: Chicago, IL

Posted Sep 30, 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…

General Labor/Construction

Company: International Leak Detection

Location: Chicago, IL

Posted Sep 30, 2025

Must possess a valid driver’s license with a clean driving record. International Leak Detection is currently seeking mature, responsible field technician…

Client Support Representative

Company: RoofingSource

Location: Niles, IL

Posted Sep 29, 2025

Hungry, resourceful, and looking to develop their skillset within the sales and operations field and learn more about commercial roofing, construction, and HVAC…

OTR CDL-A Liquid Bulk Tanker Owner Operator Drivers

Company: Liquid Cargo

Location: East Chicago, IN

Posted Sep 30, 2025

Responsible for transporting liquid bulk products across long distances *OTR, 2-3 weeks out* and *truck must have air compressor and hose rack*.

Facilities Maintenance Technician(WELDER)

Company: Central Transport

Location: Hillside, IL

Posted Sep 30, 2025

*Carpentry *– install floor tiles including ceramic and VCT, repair and hang metal/wood doors, masonry repairs, concrete repairs, drywall, and other trades.

Full Stack Software Developer

Company: Bois D'Arc International

Location: Downers Grove, IL

Posted Sep 30, 2025

The ideal candidate is proficient across the tech stack and capable of building secure, scalable, and user-friendly internal tools that improve business…

Heating, Ventilation, and Air Conditioning Technician

Company: Air Blue Heating & Cooling

Location: Wheeling, IL

Posted Sep 30, 2025

Occasional miscellaneous HVAC and mechanical equipment. Honest, dependable, and knowledgeable technician. EPA Certified (other licenses a plus).

Fabricator / Welder

Company: JX Truck Center

Location: Elmhurst, IL

Posted Sep 30, 2025

A valid driver's license with a 3 year history required. Ability to read and interpret blueprints or technical drawings. Medical - PPO and HDHP options.

Full Stack Software Engineer

Company: Unison Consulting, Inc.

Location: Chicago, IL

Posted Sep 30, 2025

This is a permanent fulltime onsite position (hybrid work environment). Net applications. Our ideal candidate is a highly motivated individual who is looking to…

Machine Operator I - 2nd Shift

Company: Ferrara Candy Company, Inc.

Location: Forest Park, IL

Posted Sep 30, 2025

Loads trays / boards on truck to be sent to the polishing room. Ability to operate and troubleshoot problems with all necessary process equipment.

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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