Flexible Schedule Jobs in Chicago, IL

34,509 open positions · Updated daily

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.

Head of Customer Service

Company: Double Good

Location: Chicago, IL

Posted Jan 24, 2025

Double Good is a company that creates joy through its delectable popcorn, easy-to-use fundraising platform, and Kids Foundation. They are seeking a Head of Customer Service to lead their growing team, focusing on strategic ownership, customer advocacy, and cross-functional partnerships. The role involves managing SaaS and BPO vendors, ensuring a safe work environment, and developing future leaders. The company offers competitive compensation, benefits, and a positive work culture.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0893)

Company: Target

Location: Itasca, IL

Posted Jan 24, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $16.50 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 in a fast-paced environment. Target values teamwork, guest satisfaction, and continuous learning.

Retail Stock Associate - Deer Park

Company: Gap Inc.

Location: Lake Zurich, IL

Posted Jan 24, 2025

Athleta, a certified B Corp, is seeking passionate individuals to join their team. The role involves executing operational and merchandising processes, maintaining a clean and organized stockroom and sales floor, and delivering excellent customer service. The company offers competitive benefits including a merchandise discount, paid time off, extensive 401(k) plan, and health insurance. Athleta is committed to diversity and inclusion, having been recognized by Forbes as one of the World's Best Employers and Best Employers for Diversity.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T1889)

Company: Target

Location: Chicago, IL

Posted Jan 24, 2025

Target, a Fortune 50 company, is hiring for a Guest Advocate role. The position involves providing exceptional guest service, including greeting guests, assisting with purchases, and resolving concerns. The role requires strong communication skills, a welcoming attitude, and the ability to multitask. The job involves working in a fast-paced environment, handling merchandise, and using technology. Target offers competitive benefits and a supportive work environment.

On-Demand: Guest Advocate (Cashier), General Merchandise, Fulfillment, Food and Beverage, Style (T1385)

Company: Target

Location: Riverwoods, IL

Posted Jan 24, 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 $16.75 - $25.15 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.

GM and Food (General Merchandise, Closing, Fulfillment, Inbound, Food and Beverage , Food Service, Starbucks) (T0838)

Company: Target

Location: Wheaton, IL

Posted Jan 24, 2025

Target, a Fortune 50 company, is seeking a General Merchandise Expert. The role involves creating a welcoming experience for guests, ensuring product availability, accurate pricing, and presentation. Responsibilities include executing daily workload, managing inventory, and maintaining a safe, compliant work environment. The ideal candidate should possess a welcoming attitude, communication skills, attention to detail, and ability to work in a fast-paced environment. Target offers training and competitive benefits.

Specialty Sales (Style, Tech, Beauty) (T1070)

Company: Target

Location: Gurnee, IL

Posted Jan 24, 2025

Target, a Fortune 50 company, is seeking a Style Consultant. The role involves providing excellent guest service, maintaining a welcoming environment, and ensuring product availability. Key responsibilities include creating a welcoming experience, understanding guest needs, maintaining an inviting shopping environment, and executing visual merchandising. The ideal candidate should have a strong interest in apparel, excellent communication skills, 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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