Flexible Work Schedule Jobs in Chicago, IL

75,610 open positions · Updated daily

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.

GM and Food (General Merchandise, Closing, Fulfillment, Inbound, Food and Beverage , Starbucks) (T1881)

Company: Target

Location: Joliet, IL

Posted Jan 23, 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. The team leads inbound, outbound, replenishment, inventory accuracy, presentation, pricing, and promotional signing processes. The job requires knowledge of guest service fundamentals, retail business fundamentals, and operational procedures. The ideal candidate should have a welcoming attitude, communication skills, attention to detail, and ability to work in a fast-paced environment.

GM and Food (General Merchandise, Closing, Fulfillment, Inbound, Food and Beverage , Food Service, Starbucks) (T1024)

Company: Target

Location: Villa Park, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is hiring for a General Merchandise Expert role. The position involves creating a welcoming experience for guests, ensuring product availability and accuracy, and executing various operational processes. The role requires a positive attitude, strong communication skills, and the ability to work in a fast-paced environment. Target offers comprehensive training and competitive benefits.

On-Demand: Guest Advocate (Cashier), General Merchandise, Fulfillment (T3214)

Company: Target

Location: Chicago, IL

Posted Jan 23, 2025

Target offers flexible on-demand work with a pay range of $17.75 - $26.65 USD per hour. On-demand team members can create their own schedules by picking up shifts via the myTime mobile app. Regular attendance is required, with shifts needed every 4 weeks. The role involves providing exceptional guest service, maintaining store appearance, and handling various tasks such as cashiering, stocking, and price accuracy. Target values team members' growth and offers training. Essential skills include focus in a fast-paced environment, communication, and physical capabilities like lifting up to 44 pounds.

Specialty Sales (Style, Tech, Beauty, Ulta Beauty) (T1881)

Company: Target

Location: Joliet, 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 ideal candidate should have a strong interest in apparel products, excellent communication skills, and the ability to work in a fast-paced environment.

General Merchandise, Closing, Fulfillment (T1889)

Company: Target

Location: Chicago, IL

Posted Jan 23, 2025

Target is offering a Fulfillment Expert position with a starting hourly rate of $17.75 USD and a pay range of $17.75 USD - $26.65 USD. The role involves a dynamic work environment, where team members help guests get what they want, when they want it, and how they want it. Responsibilities include creating a welcoming experience, engaging with guests, selecting items for order pickup, and ensuring quality and accuracy in order processing. The ideal candidate should be at least 18 years old, have a welcoming attitude, be tech-savvy, and capable of working in a fast-paced environment. Target provides training and competitive benefits.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T2373)

Company: Target

Location: Chicago, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $17.25 USD. The pay range is $17.25 USD - $25.90 USD per hour. The role involves providing exceptional guest service, engaging with guests, and promoting Target's services and benefits. Key responsibilities include greeting guests, understanding their needs, assisting with returns, and maintaining a clean work area. Target values team members' growth and offers training. The ideal candidate is energetic, communicative, and comfortable with multi-tasking in a fast-paced environment.

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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