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.

On-Demand: Guest Advocate (Cashier), General Merchandise, Fulfillment (T3221)

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.

GM and Food (General Merchandise, Closing, Fulfillment, Inbound, Food and Beverage , Food Service, Starbucks) (T2414)

Company: Target

Location: O'Fallon, 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.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0895)

Company: Target

Location: Bourbonnais, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $15.50 USD. The role involves providing exceptional guest service, promoting Target's benefits and services, and maintaining a clean work area. The job requires strong communication skills, a welcoming attitude, and the ability to work in a fast-paced environment. Target values teamwork, guest satisfaction, and continuous learning.

Food and Beverage , Starbucks, Deli, Bakery (T0533)

Company: Target

Location: Rock Island, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is seeking a Food & Beverage Expert. The role involves delivering an exceptional guest experience, maintaining food safety standards, and executing Food & Beverage processes. Previous food or grocery experience is preferred but not required. The position offers opportunities for skill development and career growth. Target values teamwork, guest service, and a fun, energetic work environment.

Pharmacy Intern - Grad

Company: CVS Health

Location: Hoffman Estates, IL

Posted Jan 23, 2025

CVS Health offers challenging opportunities for pharmacist interns to learn and grow professionally, contributing to better healthcare. As a Graduate Pharmacist Intern, you'll work under a licensed pharmacist, ensuring patient safety, and delivering exceptional care. Key responsibilities include leading with heart, supporting pharmacy staff, identifying business opportunities, and driving growth. Required qualifications include a PharmD degree, relevant work experience, and valid pharmacist intern/technician licensure. Preferred qualifications include immunization eligibility and proficiency in Microsoft Office Suite.

Wealth Management Specialist - NPD

Company: Merrill

Location: Northbrook, IL

Posted Jan 23, 2025

Merrill Wealth Management, a leading global provider of wealth management and investment services, is seeking an EGP Specialist Trainee. This role involves a training program to prepare candidates for the EGP Specialist position, focusing on marketing and sales development. The trainee will support the FA team in developing and enhancing client relationships, assisting with client meetings, and managing client service processes. Key responsibilities include tracking client activities, attending review meetings, and executing the team's service model. The ideal candidate should possess Series 7 and 66 or 7, 63, and 65 licenses, and have strong communication, organizational, and client management skills. The role is eligible for a formulaic incentive plan and offers a pay range of $24.00 - $48.08 hourly, based on experience, education, and skill set.

On-Demand: Guest Advocate (Cashier), General Merchandise, Fulfillment, Food and Beverage, Style (T0880)

Company: Target

Location: Schaumburg, IL

Posted Jan 23, 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.

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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