Flexible Hours Jobs in Chicago, IL

39,276 open positions · Updated daily

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

Risk Operations Specialist

Company: Afterpay

Location: Chicago, IL

Posted Feb 03, 2025

Cash App, a dynamic financial ecosystem, is seeking an operations professional with compliance, credit, or fraud analysis experience to join their Merchant Onboarding team. The role involves reviewing new merchants, assessing risks, and ensuring a safe, compliant, and seamless onboarding experience. The ideal candidate should have 1+ years of relevant experience, strong communication skills, and a self-starter mentality. Cash App offers competitive pay, flexible time off, and modern family planning benefits, among others, to empower employees to do their best work.

STR MGMT/BAKERY DEPT LEADER

Company: Kroger

Location: Park Ridge, IL

Posted Feb 03, 2025

Press Operator I

Company: GANNETT

Location: Peoria, IL

Posted Feb 03, 2025

Sales Intern GSIP

Company:

Location: Rolling Meadows, IL

Posted Feb 03, 2025

Team Manager

Company:

Location: Park Ridge, IL

Posted Feb 03, 2025

Frequently Asked Questions

What are typical salary ranges by seniority for flexible hours tech roles?
Entry‑level (0‑2 years) flexible‑hours engineers earn $60k–$80k annually; mid‑level (3‑5 years) range $90k–$120k; senior (5+ years) $130k–$170k, with additional shift bonuses for night or weekend coverage.
What skills and certifications are required for flexible hours positions?
Core programming languages (Python, JavaScript, Go), CI/CD tooling (Jenkins, GitHub Actions), cloud platforms (AWS, Azure, GCP), container orchestration (Kubernetes), infrastructure as code (Terraform), and Agile certifications (Certified Scrum Master, SAFe Agilist). Remote communication proficiency using Slack, Zoom, and Asana is also essential.
Is remote work available for flexible hours roles?
Over 80% of the current listings allow fully remote work, with many offering hybrid models that permit in‑office days on a flexible schedule. Employers often provide stipends for home‑office equipment and support 24‑hour VPN access.
What career progression paths exist in flexible hours tech roles?
A typical path starts with a Junior Engineer or Associate Product Manager, moves to Lead Engineer or Senior Product Owner, then to Engineering Manager or Director of Product, and ultimately to VP or Head of Engineering, each step unlocking higher pay and broader influence over product strategy.
What industry trends are shaping flexible hours tech jobs?
Tech firms are adopting continuous delivery pipelines that require 24/7 monitoring, driving demand for shift‑based DevOps and support roles. AI‑driven scheduling tools are automating shift assignment, and companies are increasingly offering flexible pay bands to retain talent in a competitive market.

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