Flexible Working Hours Jobs in Chicago, IL

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

Handyman/plumber

Company: Premier water and sewer

Location: Chicago, IL

Posted Jun 26, 2025

Utilize tools and equipment safely and effectively to complete repairs. Conduct inspections to identify issues requiring attention or repair.

Manager, Marketing FP&A

Company: PayPal

Location: Chicago, IL

Posted Jun 26, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Presentation Associate, Sr. - Mon - Fri 8:30am-5:30pm

Company: Williams Lea

Location: Chicago, IL

Posted Jun 26, 2025

Able to troubleshoot more complex or advanced tasks, equipment or software concerns on own; understands when to escalate a problem to a supervisory level.

Sr. Software Engineer

Company: Caterpillar

Location: Chicago, IL

Posted Jun 25, 2025

REQS: This position requires a bachelor’s degree, or foreign equivalent, in Computer Science, Computer Engineering, Performance, Information Management, or a…

Personal Chef (Freelance)

Company: CookinGenie LLC

Location: Chicago, IL

Posted Jun 26, 2025

Flexible Scheduling* – You set your own availability and get bookings that work for you. Showcase Your Talent* – Build your profile to highlight your menus,…

Project Manager, Office of Equity

Company: Chicago Public Schools

Location: Chicago, IL

Posted Jun 26, 2025

Build and maintain strong partnerships with school leaders, educators, parents, community organizations, city/state agencies, and other stakeholders to create a…

In-Store Product Demonstrator

Company: CDS (Club Demonstration Services)

Location: Chicago, IL

Posted Jun 26, 2025

No prior experience is required as we provide training and team support to help you succeed. Additional hours may be available upon request.

Plumber

Company: Van DerBosch Plumbing

Location: Chicago, IL

Posted Jun 26, 2025

Must have a valid driver’s license and a clean driving record. Your field experience with current plumbing license and certifications.

Retail Leasing Associate

Company: Bridge33 Capital

Location: Chicago, IL

Posted Jun 26, 2025

A minimum of 1-2 years’ leasing experience in a retail leasing or marketing role in commercial real estate; property management or related field.

Registered Nurse 2, Antepartum/Postpartum

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jun 26, 2025

17.Demonstrates accountability for own professional practice, including progress toward achievement of annual goals. 2.Maintain current BLS certification.

Utilization Review Nurse

Company: Union Health Service

Location: Chicago, IL

Posted Jun 26, 2025

Active IL RN (Registered Nurse) license / Active LPN (License Practical Nurse). Function in accordance with applicable state, federal laws and regulatory…

HVAC Lead Installer

Company: ARS-Rescue Rooter

Location: Chicago, IL

Posted Jun 26, 2025

Valid driver’s license with good driving record. EPA certification (or willingness to obtain). Disassemble and remove outdated HVAC systems, then install, start…

Frequently Asked Questions

What are typical salary ranges by seniority for Flexible Working Hours roles?
Junior (0‑2 years) usually earn $25‑$35 per hour ($52k‑$73k annually). Mid‑level (2‑5 years) ranges $35‑$50/hr ($72k‑$104k). Senior (5+ years) can command $50‑$70/hr ($104k‑$145k). These figures reflect hourly rates for contractors and full‑time roles with flexible scheduling across tech sectors.
What skills and certifications are required for Flexible Working Hours positions?
Key skills: Agile/Scrum methodology, remote collaboration via Jira/Confluence, version control (Git), CI/CD, cloud platforms (AWS, GCP, Azure), containerization (Docker, Kubernetes). Certifications: AWS Certified Solutions Architect, Certified Scrum Master, Google Professional Data Engineer, Microsoft Certified: Azure DevOps Engineer Expert.
Is remote work available for Flexible Working Hours jobs?
Most listings allow 100% remote or hybrid; a typical company offers 3‑5 remote days per week and flexible start/end times. Some roles even enable work from any location with VPN access and cloud‑based dev environments.
What are the career progression paths in Flexible Working Hours roles?
Contractor → Full‑time → Team Lead → Engineering Manager → Director of Engineering. Alternatively, a junior engineer can climb from junior to senior, then to staff or principal roles, often while maintaining flexible schedules. Upskilling in cloud, AI, or product strategy unlocks higher‑level opportunities.
What industry trends affect Flexible Working Hours?
The shift to outcome‑based performance, AI‑driven task management, and continuous delivery pipelines fuels demand for flexible schedules. Companies adopt time‑boxing, flexible sprint lengths, and asynchronous communication to reduce time‑zone friction. As a result, flexible working hours are becoming standard in tech, especially in software, data science, and product teams.

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