Flexible Schedule Jobs in Chicago, IL

34,503 open positions · 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.

Fund Accountant & Client Service Associate

Company: Port Capital LLC

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor’s degree in Accounting, Finance, or a related field. This is an excellent opportunity for a candidate with some relevant internship or entry-level…

Overnight Security Guard: Full-Time

Company: PalAmerican Security

Location: Chicago, IL

Posted Jul 08, 2025

As an Unarmed Security Guard, you will play a crucial role in maintaining the safety and security of multiple sites, ensuring a positive atmosphere for…

Sales Associate

Company: Instacart

Location: Chicago, IL

Posted Jul 07, 2025

Familiarity with tools of the trade (eg. Microsoft Office, Excel, Google Drive, Salesforce). Act as a primary point of escalation for technical issues.

Sales Representative/Merchandiser

Company: Cordialsa USA

Location: Chicago, IL

Posted Jul 07, 2025

Valid driver's license and proof of insurance. The position requires driving to grocery store customers. Ensure the effective implementation of all Marketing…

Commercial HVAC Installer

Company: Forced Air Mechanical

Location: Elk Grove Village, IL

Posted Jul 07, 2025

Valid driver’s license with a clean, insurable record. Read and interpret blueprints and mechanical drawings. OSHA 30 certification (or willing to obtain).

Project Manager - Healthcare - Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jul 08, 2025

Train and develop the project team. Our client is a design/build developer who specialize in K-12 and healthcare projects including but not limited to…

Project Manager - Multifamily Projects - Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jul 08, 2025

Ability to hire, train, and develop a team of Project Managers. Car allowance and gas compensation included. Experience on mid to large size projects.

Project Manager - Multifamily Developer

Company: Michael Page

Location: Chicago, IL

Posted Jul 08, 2025

The Project Manager is responsible for scheduling, oversight of construction and communication with project team. Bonus per project (up to 12%).

Director of Annual Giving & Alumni Engagement

Company: Sigma Alpha Epsilon Foundation

Location: Evanston, IL

Posted Jul 08, 2025

This positions lead the strategy, design, execution, and analysis of annual giving campaigns and initiatives through direct mail, email, phone, social media,…

HVAC Refrigeration Service Technician

Company: Nextech

Location: Downers Grove, IL

Posted Jul 08, 2025

EPA certification and a valid driver’s license. Diagnose and repair HVAC/R systems, including electrical, mechanical, and electronic components.

HVAC Service Technician

Company: Aire Serv

Location: Berkeley, IL

Posted Jul 08, 2025

Valid driver's license and clean driving record. We employ a front-line service system that, when followed, will consistently generate 5-star reviews.

Brand Ambassador - Sales Associate

Company: Jonathon Wesley

Location: Itasca, IL

Posted Jul 08, 2025

Safe driving record, valid driver’s license, and dependable transportation with valid insurance. Minimum requirement of a high school diploma, bachelor’s degree…

Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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