Flexible Schedules Jobs in Chicago, IL

27,628 open positions · Updated daily

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.

Creative Lead for Brand Content / Digital Experience

Company: ServiceNow

Location: Chicago, IL

Posted Feb 28, 2025

ServiceNow, a global market leader in AI-enhanced technology, is seeking a Creative Director for Digital Experiences and Content. The role involves leading the creative development of high-impact brand-building experiences across digital platforms, including social media, thought leadership, and digital media. The ideal candidate should have 15+ years of experience in the creative industry, with a proven track record of driving groundbreaking creative in B2B settings. They should be an expert in digital and social craft, with a deep understanding of UX/UI best practices and emerging content formats. The role offers a base pay of $159,400 - $279,000 plus equity, variable incentive compensation, and benefits.

Registered Nurse (RN)-Home Health-Streeterville & Surrounding Areas

Company: Luxe Home Health

Location: Streeterville, IL

Posted Feb 27, 2025

A valid IL driver’s license, auto insurance, reliable transportation, and the ability to travel throughout the service area are essential. Up to $90 per visit.

Backend Software Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 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…

Pharmacist-Drug Diversion Surveillance Analyst, Full-time Days

Company: Northwestern Medicine

Location: Chicago, IL

Posted Feb 20, 2025

We consider this on a case-by-case basis and follow all state and federal guidelines. We offer a wide range of benefits that provide employees with tools and…

Managing Associate Teacher - Little Village

Company: Carole Robertson Center for Learning

Location: Chicago, IL

Posted Feb 27, 2025

Lead the collaboration with the TA, Aides, and Program Advisor team in the creation and facilitation of studies to support weekly lesson plans, including daily…

Senior Director, Insurance Institutional Sales

Company: The Federal Home Loan Bank of Chicago

Location: Chicago, IL

Posted Feb 18, 2025

Drive Business Growth: By developing and executing strategic account plans, you’ll directly contribute to meeting sales objectives and driving significant…

AI/ML Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Mar 03, 2025

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

Lead Software Engineer in Test

Company: Beyond Finance

Location: Chicago, IL

Posted Feb 25, 2025

Beyond Finance is a rapidly growing financial technology company committed to helping individuals escape debt. They are seeking a Lead Software Development Engineer in Test to join their team. The role involves working closely with the team to verify software quality, planning and building automation, and mentoring other team members. Beyond Finance offers a collaborative work environment, competitive benefits, and opportunities for career development.

IT Technical Specialist

Company: UL Solutions

Location: Chicago, IL

Posted Mar 01, 2025

The IT Technical Specialist role involves providing C-suite technology support, managing conference room technology, performing PC imaging and deployment, troubleshooting hardware and software issues, coordinating vendor support, and managing end-user technology needs. The role requires a professional, self-motivated individual with strong communication skills, multitasking abilities, and a proven customer service background. The position involves onsite and remote support, travel, and lifting up to 50 lbs. The estimated salary range is $55,000 to $65,000, with additional benefits including health, wellness, and retirement savings. The role is part of a high-performing IT team that supports innovative companies worldwide.

Registered Nurse

Company: DAVITA

Location: Chicago, IL

Posted Feb 19, 2025

Comprehensive benefits: medical, dental, vision, 401k, paid time off, PTO cash out, DaVita-negotiated discounts on hundreds of items from your cell phone plan…

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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