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.

Cat Digital/Cat Technology - Software Engineer

Company: Caterpillar

Location: Chicago, IL

Posted Sep 09, 2025

Software Product Technical Knowledge: knowledge of technical aspects of a software product; ability to design, configure and integrate technical aspects of…

Dispatch Solutions Representative

Company: ACCEL ENTERTAINMENT

Location: Burr Ridge, IL

Posted Sep 09, 2025

Dispatch service calls to Amusement Technicians to address and/or resolve technical customer issues in the field. $19-$22 plus night shift differential pay.

Cyber Resiliency Event Response Analyst

Company: Bank of America

Location: Chicago, IL

Posted Sep 09, 2025

Strong analytical skills and the ability to assess complex situations and develop effective solutions. Responsible for developing and implementing strategies to…

Advanced Analytics Analyst Senior - Medical Economics

Company: Elevance Health

Location: Chicago, IL

Posted Sep 09, 2025

Proven ability to design modeling studies and experience with data models, addressing data quality issues in study design, and constructing robust and efficient…

Retail Leasing Associate

Company: Bridge33 Capital

Location: Chicago, IL

Posted Sep 09, 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.

Associate Brand Manager - Wasa

Company: Barilla

Location: Northbrook, IL

Posted Sep 09, 2025

Bachelor’s degree in Business Administration, Marketing, or a related field (MBA) preferred. Strategic Thinking: Ability to anticipate trends and develop…

Cat Digital/Cat Technology – Data Scientist/Technical Analyst

Company: Caterpillar

Location: Chicago, IL

Posted Sep 09, 2025

Bachelor’s degree or higher in data science, computer engineering, electrical engineering or related degree (selected candidates must complete their degree by…

Network Analyst - Security and Compliance

Company: Illinois Municipal Retirement Fund (IMRF)

Location: Oak Brook, IL

Posted Sep 08, 2025

1+ year experience working with enterprise security tools and technologies. Currently certified in GSOC OR CompTIA Security+ OR CompTIA CySA+ OR similar…

Sr. Manager Software Engineer

Company: Capital One

Location: Chicago, IL

Posted Sep 09, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

Floor Technician/Housekeeper

Company: Northbrook Health and Rehab

Location: Northbrook, IL

Posted Sep 08, 2025

Dress in appropriate uniform and be at appointed workstation promptly when the shift starts and work consistently until the shift ends.

Executive Chef (Earn up to $100k+/yr + Bonus Structure)

Company: Bavette's

Location: Chicago, IL

Posted Sep 09, 2025

Review and maintain store financials daily, including tracking food costs, and work with the General Manager to manage comps, expenses, labor, and overall…

Executive Chef

Company: Aramark

Location: Chicago, IL

Posted Sep 09, 2025

Interact directly with guests daily. Develop and maintain effective client and guest rapport for mutually beneficial business relationships.

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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