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.

Project Manager- Chicago Construction

Company: Michael Page

Location: Chicago, IL

Posted Jul 09, 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…

Overnight Security Guard

Company: KH Security Inc.

Location: Chicago, IL

Posted Jul 08, 2025

*Must have your own vehicle. *Must have a valid Perc Card and 20 hours training certificate*. KH Security Inc. provides best in class security services for…

HVAC Service Technician

Company: Aire Serv

Location: Brookfield, 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.

Marketing Graphic Designer

Company: Oak Park Park District

Location: Oak Park, IL

Posted Jul 08, 2025

Associate or bachelor’s degree in graphic design, Communications, Marketing, Electronic Media/Fine Arts, Digital Media, or related field.

Culinary Director

Company: Soul & Smoke

Location: Chicago, IL

Posted Jul 08, 2025

Driver’s license is strongly preferred. This role partners with the Chef, office team, and kitchen staff to maintain high standards while driving efficiency and…

Area Canvassing Sales Manager ($150k - $300k OTE)

Company: Zeo Energy

Location: Chicago, IL

Posted Jul 09, 2025

Our territory managers are responsible for generating leads inside their territory and maintaining business relationships with customers.

Employee Service Center Representative - Chicago

Company: MSG Entertainment Holdings, LLC

Location: Chicago, IL

Posted Jul 08, 2025

Act as the primary point of contact for employee inquiries, handling communications via phone calls, in person interactions, and ticketing system, while…

Painter

Company: Potbelly

Location: Chicago, IL

Posted Jul 08, 2025

Travel occasionally for repairs, installations, or deliveries. Competitive pay with performance-based annual raises! FSA and HSA with Employer Contribution.

Insulation Technician-Independent Contractor

Company: Green Attic Insulation

Location: Mount Prospect, IL

Posted Jul 08, 2025

Reliable transportation and valid driver's license. Operate and maintain insulation equipment and tools. Familiarity with tools and machinery used in insulation…

Union Carpenter Foreman - Data Center Hot Aisle Containment

Company: Turner Construction Company

Location: Chicago, IL

Posted Jul 09, 2025

Supervise and develop trade employees, as assigned, including providing input on or completing performance appraisals. Address staff needs and resolve problems.

Staff Accountant

Company: Windfall Group

Location: Oak Brook, IL

Posted Jul 08, 2025

Associate’s or Bachelor’s degree in Accounting, Finance, or related field. Work with property managers and construction teams to ensure invoice accuracy and…

Janitorial Working Supervisor - (ACH)

Company: GDI Services Inc US

Location: Alsip, IL

Posted Jul 08, 2025

Cleaning restrooms, break-rooms, common areas, dusting and trash removal. Respond quickly and appropriately to all customer concerns or complaints.

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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