Flexible Work Schedule Jobs in Chicago, IL

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Looking for Flexible Work Schedule jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Schedule position in the Chicago, IL area.

SR. Counsel, Digital Products, Data Analytics & Intellectual Property

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

The role involves providing legal advice and recommendations to executives and management across various business units, with a focus on technology transactions, product counseling, intellectual property, privacy, and security laws. The individual will structure and negotiate commercial agreements, collaborate with cross-functional teams, and maintain an understanding of Walgreens' digital product offerings and business goals. They will also leverage their legal expertise to mitigate business risks and contribute to financial decisions. The ideal candidate should have a Juris Doctorate, at least 5 years of post-bar legal experience, and Illinois bar membership.

Sports Director

Company: Area Scouts

Location: Chicago, IL / Remote

Posted Jan 23, 2025

Area Scouts is expanding its team and seeking experienced, self-motivated individuals with a background in coaching or playing various sports such as baseball, basketball, softball, football, volleyball, and lacrosse. The role involves working with youth athletes, maintaining relationships with local and national sports organizations, and conducting evaluations. The company emphasizes diversity, inclusion, and equal opportunity, and offers flexible full-time, part-time, temporary, internship, and contract positions with salary based on experience.

CHEMIST - ON-SITE

Company: True Value Company

Location: Cary, IL

Posted Jan 23, 2025

The job description involves a chemist applying scientific principles to formulate materials for new product development or refinement. Responsibilities include investigating new technology, researching raw materials for cost control and product improvement, preparing standards and specifications, providing technical service support, and evaluating test results. The role requires a Bachelor's Degree and 3-5 years of experience in manufacturing or chemical/paint batch processing. The work environment is climate-controlled office and warehouse, with potential travel.

Retail Sales

Company: Cracker Barrel

Location: Bloomington, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a Retail Sales team member in Bloomington, IL. The role involves managing the retail shop, providing excellent guest service, and maintaining stock. The position offers flexible hours, potential for promotion, and comprehensive training. The company values diversity, equity, and inclusion, and provides a culture of belonging, top-notch training, diverse career paths, and competitive benefits. The job requires the ability to stand for long periods, lift up to 40 pounds, and work with various food items.

Senior Staff Regulatory Specialist, Pharmaceuticals

Company: Stryker

Location: Cary, IL

Posted Jan 23, 2025

Stryker is seeking a Senior Staff Regulatory Affairs Specialist for a hybrid role in Cary, IL. The ideal candidate should be detail-oriented, collaborative, and business-oriented. They will prepare and author FDA INDs and NDAs, assess regulatory reporting mechanisms, and provide guidance to other departments. Stryker, a global medical technology leader, offers innovative products and services in various fields, impacting over 130 million patients annually. Benefits include comprehensive health and financial packages.

Dishwasher

Company: Cracker Barrel

Location: Decatur, IL

Posted Jan 23, 2025

The job posting for a Dishwasher at Cracker Barrel Old Country Store in Decatur, IL emphasizes a positive work environment. The role involves working closely with kitchen and dining room teams to ensure guest satisfaction. The company values its employees, offering a culture of belonging, top-notch training, diverse career paths, and competitive pay and benefits. Cracker Barrel is committed to diversity, equity, and inclusion, and explicitly states that racism has no place in their workplace.

Server

Company: Cracker Barrel

Location: Naperville, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store in Naperville, IL is seeking a server for a fast-paced, family-friendly environment. The role involves serving guests, maintaining a positive attitude, and working as a team to 'Please People'. Servers keep 100% of their tips and have flexible hours. The job requires standing for long periods, lifting up to 40 pounds, and working with food items. Cracker Barrel values diversity, equity, and inclusion, offering a culture of belonging, top-notch training, diverse career paths, and competitive pay and benefits.

Account Manager, RWE Clinical Trials Remote

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

Walgreens RWE Clinical Trials is hiring an Account Manager with business development, client management, and stakeholder management skills. The role involves driving the success of the Walgreens RWE Clinical Trials business segment, managing client accounts, and developing new business opportunities. The Account Manager will be responsible for achieving budgeted sales, client account development, and strategic account planning. They will also lead the proposal process, coordinate bid defense strategy, and close potential clients for clinical trials. The ideal candidate should have a scientific, sales, or marketing background with a focus on pharmaceutical/biotech, and a proven track record in developing business contacts.

Internal Consultant - Sales

Company: Deutsche Bank

Location: Chicago, IL

Posted Jan 23, 2025

DWS Group is seeking an Internal Consultant for a role in Chicago, IL. The successful candidate will be part of a team responsible for achieving sales goals across multiple territories, educating clients on DWS investment strategies, and developing skills in analytics, presentation, process, and relationship building. The role requires knowledge of investment trends and advisor practices, a Bachelor's degree, and familiarity with Morningstar Advisor Workstation and Salesforce.com. DWS offers a competitive salary, matched 401K, generous paid time off, health and mental health benefits, family-friendly benefits, and a hybrid working model. The company is committed to diversity, equity, and creating an inclusive culture.

Drive with Lyft - No Experience Needed

Company: Lyft

Location: Chicago, IL

Posted Jan 23, 2025

Lyft is offering a $700 bonus for new drivers in Chicago who complete 140 rides within the first 30 days. The company is also launching the Women+ Connect feature, aimed at enhancing the driving experience for women and nonbinary drivers. Lyft provides flexibility, with no hourly requirements and the option to cash out any time with Express Pay. Drivers can earn extra income, making it a great alternative to part-time, full-time, or seasonal jobs. No prior experience is needed, but transportation industry experience is beneficial.

Drive with Lyft - Features made for women + enby drivers

Company: Lyft

Location: Chicago, IL

Posted Jan 23, 2025

Lyft is offering a $700 bonus for new drivers in Chicago who complete 140 rides within the first 30 days. The company is also launching the Women+ Connect feature, aimed at enhancing the driving experience for women and nonbinary drivers. Lyft provides flexibility, with no hourly requirements and the option to cash out any time with Express Pay. Drivers can earn extra income, making it a great alternative to part-time, full-time, or seasonal jobs. No prior experience is needed, but transportation industry experience is beneficial.

Frequently Asked Questions

What are typical salary ranges for flexible work schedule roles at different seniority levels?
Entry‑level (0‑2 years) $60k–$80k; Mid‑level (2‑5 years) $80k–$120k; Senior (5‑10 years) $120k–$180k; Lead/Principal (10+ years) $180k–$250k. International remote roles may have adjusted ranges such as $40k–$60k in emerging markets, reflecting local cost of living while maintaining equity.
What key skills and certifications are required for flexible work schedule positions?
Technical: Proficiency in Git, Docker, Kubernetes, and cloud platforms (AWS Certified Solutions Architect, Google Cloud Professional Data Engineer, or Azure Solutions Architect). Agile and project tools: Jira, Confluence, and automated testing frameworks. Soft skills: asynchronous communication, cultural competence, self‑management, and time‑zone coordination. Certifications like Certified Scrum Master (CSM), ITIL Foundation, and PMP are highly regarded for product and project roles.
Is remote work always an option for flexible schedule roles?
Most flexible schedule positions offer 100% remote or hybrid arrangements, with occasional on‑site requirements for quarterly collaboration or training. Companies often specify the percentage of remote work (e.g., 80% remote, 20% on‑site) and provide stipends for home‑office equipment. Applicants can verify the remote policy in the job description or during the interview.
What career progression paths exist within flexible work schedule roles?
Typical paths include: Junior Engineer → Senior Engineer → Tech Lead → Principal Engineer → Engineering Manager; or Product Manager → Senior Product Manager → Director of Product → VP of Product. Lateral moves into architecture, security, or data science are common for professionals seeking broader impact while maintaining flexible arrangements.
What are the current industry trends affecting flexible work schedule jobs?
Key trends: growth of asynchronous communication tools (e.g., Loom, Notion), AI‑driven workflow automation (e.g., GitHub Copilot, ChatGPT for code review), distributed version control at scale, micro‑tasking platforms, flexible sprint lengths, well‑being metrics integration, and digital nomad visas supporting cross‑border talent. Companies are also investing in continuous learning portals and remote‑first hiring practices.

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