Flexible Hours Jobs in Chicago, IL

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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.

Network Engineer

Company: Ascend Technologies

Location: Chicago, IL

Posted Jan 28, 2025

Ascend Technologies is seeking a Network Engineer with strong project management, organizational, and communication skills. The role involves operational support for clients' network infrastructure, including switches, routers, wireless access points, controllers, and firewalls. The candidate will also be involved in building, configuring, and securing network infrastructure. Key responsibilities include addressing escalated tickets, maintaining client networks, communicating with clients, assisting with projects, and participating in an on-call rotation. Preferred skills include a Bachelor's degree in Computer Science or related field, minimum 3 years of Network Engineering experience, knowledge of VoIP technologies, experience with network technologies from Fortinet, Cisco, Aruba, Palo Alto, and Ubiquiti, and extensive knowledge of network protocols, services, and monitoring tools. Cisco CCNA and/or CCNP or Fortinet FCP certification or equivalent working experience is required. The company values diversity, equity, and inclusion, and is committed to fostering an environment where every individual feels valued, respected, and empowered. The starting salary expectations are $80000+.

Technical Product Analyst

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 28, 2025

McDonald's is accelerating its growth strategy, focusing on Delivery, Digital, and Drive-Thru. The company aims to leverage AI, robotics, and emerging tech to digitize the Golden Arches and enhance customer experience. The Technical Product Analyst role is part of the Global Technology Infrastructure & Operations team, responsible for optimizing user experience, conducting user research, and translating insights into product strategy. The role requires a self-starter with strong project management skills, analytical capabilities, and excellent communication skills.

Lead Product Owner, Cat Foresight - Planned Maintenance (PM) (Remote)

Company: Caterpillar

Location: Peoria, IL

Posted Jan 28, 2025

Caterpillar Inc. is seeking a Lead Product Owner for the Cat Foresight Planned Maintenance product. The role involves close collaboration with various teams, understanding business needs, setting product direction, driving development, managing costs, and ensuring product quality. The ideal candidate should have a degree, experience in digital product ownership, practical domain expertise in Cat business processes, and strong skills in digital product strategy, user-centric design, data analysis, and technical fluency. The position offers a competitive salary, benefits, and opportunities for career growth and working with emerging technologies.

Associate Director, Time & Pay Technology​

Company: Kraft Heinz

Location: Chicago, IL

Posted Jan 28, 2025

The Associate Director of Time and Pay Technology at Kraft Heinz will lead the development and implementation of HR tech, ensuring alignment with engineering best practices. This role involves collaborating with cross-functional teams, optimizing HR systems, and managing a team of HR technology specialists. The ideal candidate will have significant experience in digital HR products, product strategy, and software engineering team leadership. The role is based in Chicago, IL, and offers a competitive salary range of $159,400 - $199,200, along with comprehensive benefits and wellbeing programs.

Design & UX Manager (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 28, 2025

Enova Studios is seeking a User Experience and Design Leader with 7-10 years of experience in UX design, including people management. The role involves leading a team of designers, fostering relationships with product and engineering teams, and driving a data-driven design approach. The ideal candidate will have expertise in creating and maintaining wireframe systems, user flows, prototypes, and specifications. Enova offers a competitive salary range, comprehensive benefits, and a values-driven work environment.

Manager Digital Project

Company: Caterpillar

Location: Peoria, IL

Posted Jan 28, 2025

Caterpillar Inc. is seeking a project manager for its Integrated Procurement (IP) platform, the largest ecommerce platform of the company. The role involves overseeing project activities, developing contingency plans, managing a global team, and ensuring adherence to quality standards. The ideal candidate should have strong Excel skills, experience with MS Project, multitasking abilities, technical aptitude, and excellent communication skills. Caterpillar offers a flexible hybrid work environment, competitive compensation, and benefits, including a 401k savings plan, health savings account, and tuition reimbursement. The job description is intended as a general guide and may be subject to change based on organizational needs.

Database Administrator

Company: Belvedere Trading

Location: Chicago, IL

Posted Jan 28, 2025

Belvedere Trading, a leading proprietary trading firm based in Chicago, is seeking a skilled Database Administrator. The role involves supporting SQL Server, Google BigQuery, and Google Cloud SQL databases, optimizing performance, collaborating with developers, and maintaining monitoring systems. The ideal candidate should have proven experience in SQL Server infrastructure, query optimization, and performance tuning. Familiarity with cloud data warehouses and modern tools is beneficial. Excellent communication and problem-solving skills are required. Belvedere values diversity and inclusion, and encourages applications from all backgrounds.

IT Analyst - Applications

Company: Caterpillar

Location: Peoria, IL

Posted Jan 28, 2025

Caterpillar Inc. is seeking a professional with expertise in agile development, data analytics, and ETL processes. The role involves analyzing customer requirements, discerning data accuracies, researching and documenting data specifications, and understanding software development and web technologies. The successful candidate will work with systems integration, database design, and cloud computing. Caterpillar offers a comprehensive total rewards package, including medical, dental, vision coverage, 401k, and potential annual bonuses. The primary locations for this position are East Peoria, IL, Nashville, TN, and Dallas, TX.

Senior Tax Accountant - Partnerships

Company: Wipfli

Location: Chicago, IL

Posted Jan 28, 2025

Wipfli is a company that values its employees and offers a career-defining opportunity for a Senior Manager in Partnership Tax. The role involves conducting primary and secondary reviews of complex tax returns, providing tax consulting services, and collaborating with the Partnership Tax team to make recommendations on return preparation and tax savings opportunities. The responsibilities also include managing staff, adhering to budgets and deadlines, and developing expertise in Subchapter K Partnership taxation. The company offers high-quality tools and resources, and emphasizes accuracy, quality, and client service. The estimated base pay range for this role is $75,000 to $116,000, and the company provides a variety of benefits to support employee wellbeing.

Revenue Integrity Analyst

Company: Keystone Advisors LLC

Location: Chicago, IL

Posted Jan 28, 2025

Keystone Advisors is seeking a Revenue Integrity Analyst to support a healthcare client in Chicago, IL. The role involves managing large data-driven projects across the Cook County Health Physician Revenue Services and Hospitals System. The analyst will ensure the charge description master file adheres to system policy, reflects clinical practice, and aligns with reporting requirements. Key responsibilities include managing Siemens and Cerner Patient Accounting tables, creating utilization management reports, automating manual processes, analyzing Revenue Cycle data, and responding to enhancement requests. Preferred qualifications include a Bachelor's degree in Business, Finance, Health Administration, or related field, 3+ years of Revenue Cycle experience, proficiency in Excel, Access, SQL, and Visual Basic, and strong analytical and communication skills.

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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