Flexible Working Hours Jobs in Chicago, IL

63,137 open positions · Updated daily

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.

Sales and Marketing Representative

Company: SERVPRO

Location: Broadview, IL

Posted Apr 18, 2025

In this role you will be meeting with potential customers to help develop our customer base and exceed sales goals via route selling, continuing education…

View Details Apply on SimplyHired

Data Analyst - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

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Database Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

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Web Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

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Full Stack Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired
staffing agency contract travel

Travel Interventional Radiology Technologist - $2,735 per week

Company: MedPro Healthcare Allied Staffing

Location: Chicago, Illinois

Posted Apr 20, 2025

View Details Apply on healthecareers.com

Tax Services Manager - FSO - GCR/Insurance EDGE

Company: EY

Location: Chicago, IL

Posted Apr 18, 2025

Direct experience in state and local taxation (e.g., state return compliance, state income tax accounting, state apportionment fundamentals).

View Details Apply on SimplyHired

Senior Data Engineer / Analytic Engineer

Company: Velvetech

Location: Chicago, IL

Posted Apr 18, 2025

As a Senior Data Engineer / Analytic Engineer (Microsoft Fabric), you will lead the design, implementation, and optimization of data engineering pipelines and…

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Back End Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired

Residential Service Plumber

Company: Olympian Plumbing LLC

Location: Niles, IL

Posted Apr 17, 2025

Possession of a valid plumbing license or certification in compliance with local regulations. Valid driver's license and a clean driving record.

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Front-End Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

View Details Apply on SimplyHired

Power BI Developer

Company: Velvetech

Location: Chicago, IL

Posted Apr 18, 2025

Design, develop and support data analytics using Power BI service, self-service models, and visualization tools. Experience with differen large language models.

View Details Apply on SimplyHired

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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