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.

Training and Knowledge Specialist

Company: Caterpillar

Location: Peoria, IL

Posted Jan 29, 2025

Caterpillar Inc. is seeking a highly accountable individual with strong communication and organization skills for a role in their Digital and Data Technology area. The successful candidate will develop training materials, identify training needs, and lead training initiatives for the Cat Digital Support Center. They will also partner with third-party contact centers in launching new programs and ongoing operations. The role involves deploying various training methods, ensuring a seamless handoff of training and quality to third-party suppliers, and regularly reviewing curriculum materials. The position requires a college degree or equivalent experience in progressive training assignments, strong communication skills, and contact center experience. Caterpillar offers a flexible hybrid work environment, competitive compensation, and benefits, and is committed to a reduced-carbon future.

Operations Technology People Manager

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 29, 2025

McDonald's is seeking a Service Delivery Manager to lead the Operations Technology People (OTP) Program, which supports the increasing technology footprint across nearly 14,000 McDonald's restaurants in the US. The role involves strategic leadership, program management, event management, communications, training, technology deployment, incident management, relationship management, budget management, project execution, and process improvement. The ideal candidate should have 10+ years of overall business experience, 5+ years of project management experience, exceptional communication skills, and proficiency in Microsoft Office Suite. The position offers health and welfare benefits, a 401k plan, educational assistance, flexible working arrangements, and time off policies.

Salesforce Developer (Remote)

Company: Inspira Financial

Location: Chicago, IL

Posted Jan 29, 2025

Inspira Financial is seeking talented Software Engineers to join their cross-functional DevOps-based Agile team. The ideal candidate will have expertise in both frontend and backend coding languages, development frameworks, and third-party libraries. They should possess strong programming skills, data and database skills, cloud skills, and experience with containers and Kubernetes. The role involves collaborating with users, engineers, designers, and product managers to foster ideation and deliver cutting-edge software solutions. The Software Engineer II will report to the Director of Software Engineering in the Technology Department. Inspira Financial offers competitive compensation and benefits, and has been recognized for its remarkable growth and outstanding workplace culture.

Senior Tax Analyst

Company: ZS

Location: Chicago, IL

Posted Jan 30, 2025

Sr. Manager, Global Capability Development

Company: Kraft Heinz

Location: Chicago, IL

Posted Jan 29, 2025

Kraft Heinz is offering a Senior Manager Global Capabilities position with a base salary range of $118,400 - $148,000. The role involves enhancing the company's future capabilities through global strategy development and implementation. Key responsibilities include championing a culture of continuous learning, identifying capability gaps, and collaborating with cross-functional teams. The ideal candidate should have strong relationship management, communication, analytical, and presentation skills. Kraft Heinz provides comprehensive benefits, including wellness programs, total rewards, and a flexible spectrum of programs to support diverse workforce needs.

Senior Product Manager- Product strategy

Company: Ahold Delhaize USA

Location: Chicago, IL

Posted Jan 29, 2025

Ahold Delhaize USA is seeking a Product Strategy and Experimentation Manager for its Chicago office. The role involves driving strategic planning, managing the digital product roadmap, and leading a team of two product managers. The ideal candidate should have experience with agile development, cross-functional team leadership, and project management skills. The company offers a competitive salary range of $131,520 to $204,240 and values diversity, equity, inclusion, and wellness.

Credit Analyst (Due Diligence Analyst)

Company: Rewards Network

Location: Chicago, IL

Posted Jan 29, 2025

Rewards Network, a company celebrating 40 years in business, offers financial marketing services and dining rewards programs to increase restaurant revenue, traffic, and customer engagement. They leverage advanced technology and data analytics for their unique card-linked offers. The company culture is collaborative, diverse, and passionate, with a focus on problem-solving and career growth. The Due Diligence Analyst Underwriter role involves risk assessment, underwriting of financial services products, and collaboration with sales teams. The position requires strong analytical skills, proficiency in MS Excel, and excellent communication skills. The company offers a comprehensive benefits package, including a competitive salary, paid time off, dining reimbursement, 401k plan, health insurance, and more. The expected pay range is $60,000-$75,000 USD.

Operations Technology People Manager Manager

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 29, 2025

McDonald's is seeking a Service Delivery Manager to lead the Operations Technology People (OTP) Program, which supports the increasing technology footprint across nearly 14,000 McDonald's restaurants in the US. The role involves strategic leadership, program management, event management, communications, training, technology deployment, incident management, relationship management, budget management, project execution, and process improvement. The ideal candidate should have 10+ years of overall business experience, 5+ years of project management experience, exceptional communication skills, and proficiency in Microsoft Office Suite. The position offers health and welfare benefits, a 401k plan, educational assistance, flexible working arrangements, and time off policies.

RN - Home Health - PRN

Company:

Location: Decatur, IL

Posted Jan 30, 2025

Software Engineer (Chicago)

Company: Nextpoint

Location: Chicago, IL

Posted Jan 29, 2025

Nextpoint, an award-winning team, offers transformative software and services for law firms. They value innovation, creativity, diversity, and initiative, fostering a happy workplace. The Level 2 Support Engineer role involves creating and maintaining a high-performing, reliable environment for clients, collaborating with engineering and product teams, and continuously improving system performance. The ideal candidate has a Bachelor's degree in computer science, 2+ years of support engineering experience, and strong problem-solving skills.

Payment Specialist

Company: Rewards Network

Location: Chicago, IL

Posted Jan 29, 2025

Rewards Network, a company celebrating 40 years in business, is seeking a Payments Specialist. The role involves processing payments, reconciling accounts, and maintaining client relationships. The ideal candidate will have a background in bookkeeping, accounting, or payments, with excellent interpersonal and organizational skills. The company offers a comprehensive benefits package, including health insurance, retirement plans, and a flexible working space.

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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