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.

Specialty Sales (Style, Tech, Beauty) (T1888)

Company: Target

Location: Rosemont, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Style Consultant position with a starting hourly rate of $16.75 USD. The role involves providing excellent guest service, maintaining product availability, and creating an inviting shopping environment. Key responsibilities include greeting guests, understanding their needs, replenishing the sales floor, and executing visual merchandising. The position requires strong interest in apparel, effective communication, and the ability to work in a fast-paced environment. Target values teamwork, guest satisfaction, and offers comprehensive benefits.

Independent Optometrist - Walmart

Company: Walmart

Location: Rock Island, IL

Posted Jan 23, 2025

The text describes a job opportunity for an Independent Optometrist leasing space inside Walmart stores. The role involves leading patient care in eye and vision care, general health, and well-being. The optometrist has autonomy over their practice hours, patient schedule, and fee schedule, retaining 100% of exam/professional fees. They can opt into equipment/instrumentation and administrative support services. Minimum qualifications include a Doctor of Optometry (OD) or Ophthalmologist (MD or DO) license, valid state license, and insurance certificates. The job is not an employment position with Walmart Inc.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0868)

Company: Target

Location: Crestwood, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $16.75 USD. The position involves providing exceptional guest service, engaging with guests, and promoting Target's services and benefits. The role is dynamic, involving tasks like scanning, bagging, and maintaining a clean work area. Target values teamwork, communication, and a positive attitude. No two days are the same, with responsibilities ranging from assisting guests to managing returns and utilizing technology.

Risk Adjustment Program Manager

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health is seeking a Program Manager for their Risk Adjustment Retrospective Program, covering ACA, Medicare, MMP, and DSNP lines of business. The role involves provider/vendor/network outreach, production management, and reporting. The ideal candidate should have 5-7 years of work experience, strong analytical skills, and the ability to work in a fast-paced environment. Preferred qualifications include risk adjustment program experience within Medicare and a Bachelor's Degree. The pay range is $54,300.00 - $145,860.00, with additional benefits such as medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and more.

Retail Sales Associate - Northridge Center

Company: Gap Inc.

Location: Rock Island, IL

Posted Jan 23, 2025

Old Navy is a fashion retailer that aims to democratize style and make shopping enjoyable. They offer high-quality, affordable essentials for the whole family. The company, founded in 1994, values a fun, fast-paced work environment and community. The role involves providing excellent customer service, product expertise, and promoting brand loyalty. Benefits include a merchandise discount, competitive PTO, volunteer time, extensive 401(k), health insurance, and a commitment to diversity and inclusion.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0928)

Company: Target

Location: Niles, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $17.00 USD. The role involves providing exceptional guest service, engaging with guests, and promoting Target's services and benefits. The job requires strong communication skills, a welcoming attitude, and the ability to handle multiple tasks in a fast-paced environment. Target values teamwork, guest satisfaction, and continuous learning.

Staff Engineer - Android

Company: CVS Health

Location: Buffalo Grove, IL

Posted Jan 23, 2025

CVS Health is seeking a Staff Engineer - Android to work on the customer-facing Flagship CVS app. The role involves advancing architecture and mobile product, partnering with cross-functional teams, and mentoring team members. The ideal candidate should have 7+ years of software development experience, with at least 7+ years in designing/developing Android mobile applications. They should be a subject matter expert in software engineering best practices and the Health and e-Commerce domain. Responsibilities include developing Android code, improving CI/CD infrastructure, collaborating on solutions to reduce cost and time to market, and providing technical guidance to fellow engineers.

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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