Flexible Schedules Jobs in Chicago, IL

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

SEO Manager

Company: Vivid Seats

Location: Chicago, IL

Posted Feb 03, 2025

Vivid Seats, a leading online ticket marketplace founded in 2001, is seeking an experienced SEO Manager. The role involves developing and leading the company's SEO roadmap, identifying opportunities for organic search presence, and collaborating with cross-functional teams. The ideal candidate should have 5+ years of enterprise SEO experience, a deep understanding of SEO facets, and expertise in keyword research, on-page optimization, and content development. The role offers a competitive salary range of $110,000-$140,000 USD/CAD, along with comprehensive benefits and a flexible hybrid working model in Chicago, IL.

Press Operator I

Company: GANNETT

Location: Peoria, IL

Posted Feb 03, 2025

Registered Nurse

Company: DaVita

Location: Mount Vernon, IL

Posted Feb 03, 2025

Team Manager

Company:

Location: Park Ridge, IL

Posted Feb 03, 2025

Store Manager

Company:

Location: Bloomington, IL

Posted Feb 03, 2025

Pharmacy Technician

Company: CVS Health

Location: Ottawa, IL

Posted Feb 03, 2025

Sales Intern GSIP

Company:

Location: Rolling Meadows, IL

Posted Feb 03, 2025

Frequently Asked Questions

What are typical salary ranges for flexible‑schedule tech roles by seniority?
Junior developers in flexible settings earn $60k–$90k, mid‑level engineers $90k–$140k, senior engineers $140k–$200k, and tech leads or product managers $160k–$250k, with variations based on location, stack, and remote cost adjustments.
Which skills and certifications are most valuable for flexible‑schedule positions?
Proficiency in Git, CI/CD pipelines, and cloud platforms (AWS, Azure, GCP) is essential. Remote collaboration tools like Slack, Zoom, and Jira are standard. Certifications such as AWS Certified Solutions Architect, Certified Scrum Master, or Google Cloud Professional Data Engineer boost credibility.
How common is remote work availability in flexible‑schedule roles?
Over 80% of the 1501 listings allow full remote work, with 15% offering hybrid models that require 1–2 on‑site days per month. Companies set core hours (e.g., 10 am–3 pm UTC+2) to synchronize cross‑time‑zone teams.
What career progression paths exist within flexible‑schedule tech teams?
Typical paths move from Junior Engineer to Senior Engineer, then to Technical Lead or Engineering Manager, and ultimately to VP of Engineering or CTO. Roles such as Product Owner, UX Lead, or Data Engineering Lead also offer vertical growth while maintaining schedule flexibility.
What industry trends are shaping the future of flexible schedules?
The industry is moving toward AI‑driven scheduling tools that auto‑align meetings with optimal personal productivity windows. Companies are adopting outcome‑based performance metrics instead of fixed hours, and the demand for mental‑health‑friendly work hours is rising across all tech sectors.

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