Flexible Working Hours Jobs in Chicago, IL

63,147 open positions · Updated daily

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

Senior HR Generalist

Company: Invenergy

Location: Chicago, IL

Posted Jan 28, 2025

Invenergy is seeking a Senior HR Generalist for their Canadian operations. The role involves supporting employees in all HR areas, including policy development, performance management, and compliance with Canadian employment laws. The ideal candidate will have a Bachelor's degree in HR or a related field, at least 5 years of progressive HR experience, and strong knowledge of Canadian employment laws. The position offers a base salary range of $92,000 to $115,000 USD annually, with potential for bonuses. Invenergy is an equal opportunity employer.

Call Center Supervisor, Customer Service (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 28, 2025

Enova International is seeking a Call Center Supervisor with 3 years of leadership experience in a related capacity, preferably within the financial industry. The role involves overseeing a team of representatives, teaching, training, and mentoring them to ensure a quality customer experience. The successful candidate will manage metrics, review quality assurance reports, conduct meetings, and assist with new hire interviews and onboarding. The position offers a competitive salary range and comprehensive benefits, including health, dental, vision insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Enova is a values-driven organization committed to making accessible credit for millions through its AI and machine learning-powered Colossus platform.

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.

Applied AI Intern

Company: iManage

Location: Chicago, IL

Posted Jan 29, 2025

iManage offers a paid internship program for students interested in AI and data science. The program, based in Chicago, runs from June 2nd to August 8th and includes project-based activities, team building, and social events. Interns will work with a multidisciplinary team of AI engineers and data scientists, focusing on researching and applying cutting-edge Gen AI algorithms and NLP methods. The role involves performing exploratory data analyses, developing prompt engineering techniques, and conducting research experiments. Qualified candidates should have proficiency in data structures, algorithms, and statistics, current enrollment in a relevant graduate program, and experience with Python packages for text data analysis.

Reporting Analyst

Company: Alliant Credit Union

Location: Chicago, IL

Posted Jan 29, 2025

This role involves optimizing operational processes, providing valuable report insights, and leveraging data analysis to identify areas for improvement. The individual will develop and maintain operational reports, collaborate with other departments, and ensure data integrity. The position requires a Bachelor's degree in Finance, Economics, Mathematics, Business, or a related field, and at least 3 years of experience in data analytics, finance, or a related field. The compensation range is $61,700 to $94,750 annually, with additional benefits including health care, vision, dental, 401k with employer match, work from home options, paid parental leave, employee discount programs, time off, 11 paid holidays, and education reimbursement. The role also involves adhering to and ensuring compliance with the Bank Secrecy Act and maintaining integrity and ethics in all actions and conversations regarding credit union members and their accounts.

Lead Compliance Tester

Company: Discover

Location: Chicago, IL

Posted Jan 29, 2025

Discover is offering a job opportunity for a Compliance professional with 4+ years of experience in Financial Services Risk, BSAAML, or related fields. The role involves assessing business processes and controls for regulatory compliance, developing test scripts, and collaborating with management to identify and address compliance issues. The company values diversity and inclusion, and offers a competitive compensation package, benefits, and opportunities for growth. The position requires a Bachelor's degree in Business Administration, Management, Finance, or Law, and the ability to work in an office setting.

Customer Success Manager - RCM

Company: Neolytix

Location: Chicago, IL

Posted Jan 29, 2025

Neolytix, a leading provider of healthcare management services, is seeking a proactive and client-focused Customer Success Manager for Medical Billing. The role involves managing client relationships, improving service delivery, driving customer satisfaction, and reducing revenue leakage. The ideal candidate should have a Bachelor's degree in healthcare administration or a related field, 2+ years of experience in practice management or revenue cycle management within the healthcare industry, and strong knowledge of medical billing software and data analytics platforms. Neolytix values problem solvers and client-focused professionals dedicated to driving results, offering a mission to elevate healthcare provider organizations through data-driven strategies and exceptional client service.

Lead Cybersecurity Engineer

Company: Beyond Finance

Location: Chicago, IL

Posted Jan 28, 2025

Beyond Finance is seeking an experienced Cybersecurity Engineer to design and enforce security policies, protect the organization's computing infrastructure, and ensure network and data security. The ideal candidate will have a degree in Computer Science, professional information security certification, strong analytical skills, and leadership abilities. Beyond Finance offers a collaborative work environment, competitive benefits, and opportunities for career development.

Product Manager (General Consideration) (Remote)

Company: Inspira Financial

Location: Chicago, IL

Posted Jan 28, 2025

Inspira Financial is seeking a Product Manager to join their innovative build team, designing a state-of-the-art greenfield platform for Health & Benefits customers. The role involves contributing to product strategy and delivery, managing a team of engineers, and defining a product roadmap. The ideal candidate should have a Bachelor's degree in business, marketing, computer science, or a related field, with 3+ years of experience in product management. They should possess strong understanding of software development processes, Agile methodologies, and cross-functional collaboration skills. Familiarity with product management tools and analytical mindset are also required. A background in Healthcare, HealthTech, Finance, FinTech, or start-ups is preferred, along with knowledge of UX/UI principles and customer-centric design.

Sr .NET Developer (Perm - Hybrid at our Chicago HQ near O'Hare Airport)

Company: Alliant Credit Union

Location: Chicago, IL

Posted Jan 29, 2025

This role involves designing, developing, and implementing platform solutions in an agile team, utilizing full stack development tools and technologies such as .NET, Web, and MuleSoft. The role requires a Bachelor's degree in Computer Science or related field and at least 3 years of experience in .NET APIs and Microservices application development. The position offers a competitive salary range, benefits including health care, 401k, and work from home options. The role also emphasizes adherence to Bank Secrecy Act policies and maintaining integrity and ethics in all actions.

Frequently Asked Questions

What are typical salary ranges by seniority for Flexible Working Hours roles?
Junior (0‑2 years) usually earn $25‑$35 per hour ($52k‑$73k annually). Mid‑level (2‑5 years) ranges $35‑$50/hr ($72k‑$104k). Senior (5+ years) can command $50‑$70/hr ($104k‑$145k). These figures reflect hourly rates for contractors and full‑time roles with flexible scheduling across tech sectors.
What skills and certifications are required for Flexible Working Hours positions?
Key skills: Agile/Scrum methodology, remote collaboration via Jira/Confluence, version control (Git), CI/CD, cloud platforms (AWS, GCP, Azure), containerization (Docker, Kubernetes). Certifications: AWS Certified Solutions Architect, Certified Scrum Master, Google Professional Data Engineer, Microsoft Certified: Azure DevOps Engineer Expert.
Is remote work available for Flexible Working Hours jobs?
Most listings allow 100% remote or hybrid; a typical company offers 3‑5 remote days per week and flexible start/end times. Some roles even enable work from any location with VPN access and cloud‑based dev environments.
What are the career progression paths in Flexible Working Hours roles?
Contractor → Full‑time → Team Lead → Engineering Manager → Director of Engineering. Alternatively, a junior engineer can climb from junior to senior, then to staff or principal roles, often while maintaining flexible schedules. Upskilling in cloud, AI, or product strategy unlocks higher‑level opportunities.
What industry trends affect Flexible Working Hours?
The shift to outcome‑based performance, AI‑driven task management, and continuous delivery pipelines fuels demand for flexible schedules. Companies adopt time‑boxing, flexible sprint lengths, and asynchronous communication to reduce time‑zone friction. As a result, flexible working hours are becoming standard in tech, especially in software, data science, and product teams.

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