Flexible Schedule Jobs in Chicago, IL

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

Specialty Sales (Style, Tech, Beauty, Ulta Beauty) (T1176)

Company: Target

Location: Arlington Heights, IL

Posted Jan 22, 2025

Target, a Fortune 50 company, is seeking a Style Consultant. The role involves providing excellent guest service, maintaining a welcoming and organized sales floor, and staying updated on industry trends. Key responsibilities include creating a guest-ready shopping environment, executing visual merchandising, and ensuring product availability. The ideal candidate should have a strong interest in apparel, excellent communication skills, and the ability to work in a fast-paced environment.

Systems Engineer / Architect

Company: Leidos

Location: O'Fallon, IL

Posted Jan 22, 2025

Store Executive Intern (Store Leadership Intern)-Broadview, IL (Starting Summer 2025)

Company: Target

Location: North Riverside, IL

Posted Jan 22, 2025

Target is offering a paid 40-hour-per-week Stores Executive Leadership Internship. This program aims to provide a realistic job preview of an Executive Team Leader (ETL) role, teaching skills such as guest service fundamentals, retail business acumen, team management, and business strategy development. Interns will work closely with mentors, learn to lead a team, drive sales, and provide exceptional guest service. The role involves leading daily operations, addressing team member concerns, and participating in developmental activities. Target values leaders who are adaptable, have strong communication skills, and demonstrate a commitment to ethical conduct and safety.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0842)

Company: Target

Location: Orland Park, IL

Posted Jan 22, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $16.75 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 multitask. Target values teamwork, guest satisfaction, and continuous learning. The role is fast-paced, involving tasks like scanning, bagging, and assisting with returns, while maintaining a clean work area.

Specialty Sales (Style, Tech, Beauty) (T1213)

Company: Target

Location: Bolingbrook, IL

Posted Jan 22, 2025

Target, a Fortune 50 company, is seeking a Style Consultant. The role involves providing excellent guest service, maintaining a welcoming and organized sales floor, and staying updated on industry trends. Key responsibilities include creating a guest-ready shopping environment, executing visual merchandising, and ensuring product availability. The ideal candidate should have a strong interest in apparel, excellent communication skills, and the ability to work in a fast-paced environment.

Full-Time Beauty Lead Advisor - Sephora

Company: Kohl's

Location: Tinley Park, IL

Posted Jan 22, 2025

The Beauty Lead Advisor role at Kohl's involves driving sales through a genuine passion for beauty, engaging clients with a consultative approach, and maintaining expert knowledge of top beauty brands. Key responsibilities include building client loyalty, influencing product sales, demonstrating products, executing sales plans, maintaining visual merchandising standards, and ensuring timely sales floor replenishment. The role requires client-facing retail experience, excellent communication skills, and the ability to work flexible hours. Benefits include work-life balance, health & wellness programs, savings & retirement benefits, insurance programs, and support for life events.

On-Demand: Guest Advocate (Cashier), General Merchandise, Fulfillment, Food and Beverage, Style (T0957)

Company: Target

Location: Villa Park, IL

Posted Jan 22, 2025

Target offers an On-Demand role with flexible scheduling, allowing employees to work as much or as little as they like. The pay range is $16.50 - $24.75 per hour. Regular attendance is necessary, with a requirement to work at least one shift every 4 weeks. The role involves advocating for guest experience, providing excellent service, and engaging with guests. No two days are the same, with responsibilities including greeting guests, solving concerns, and promoting Target's services and benefits. The job requires strong communication skills, a welcoming attitude, and the ability to work in a fast-paced environment.

Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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