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.

Cook

Company: Cracker Barrel

Location: O'Fallon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a Cook to join their kitchen team. The role involves preparing a full menu of Southern favorites using Cracker Barrel's recipes and methods. The Cook will ensure high standards of professional cooking, quality, safety, cleanliness, and hospitality. Flexible hours are available, and there are opportunities for promotion and continued development. The company values diversity, equity, and inclusion, and offers a culture of belonging, top-notch training, diverse career paths, and competitive pay and benefits.

Cook

Company: Cracker Barrel

Location: Marion, IL

Posted Jan 23, 2025

Mid-Market Sales Executive

Company: PHMG

Location: Chicago, IL

Posted Jan 23, 2025

PHMG, a leading audio branding agency celebrating its 23rd anniversary, is recruiting Mid-Market Sales Executives. The role involves cold calling, building relationships with prospects, and closing deals. Successful candidates will enjoy a competitive salary, uncapped commission, and various incentives. PHMG offers comprehensive training, a supportive work environment, and attractive benefits including health benefits, 401k, and gym membership.

Retail Sales

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

H&M Sales Associate

Company: H&M

Location: Schaumburg, IL

Posted Jan 23, 2025

Part-Time Assistant Manager

Company: Cinemark

Location: Lisle, IL

Posted Jan 23, 2025

(USA) Associate Optometrist - Walmart $20,000 Sign On Bonus

Company: Walmart

Location: Springfield, IL

Posted Jan 23, 2025

Walmart is seeking an Associate Optometrist to join their team, revolutionizing healthcare by providing affordable eyecare. The role involves delivering evidence-based vision care, connecting with patients, and operating the business autonomously. The ideal candidate will have strong clinical knowledge, a business mindset, and a passion for community involvement. Benefits include competitive pay, performance bonuses, and various health, financial, and time-off benefits.

Server

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a server for their Effingham location. The role involves serving guests in a fast-paced, family-friendly environment, with the mission of 'Pleasing People'. Servers keep 100% of their tips and have flexible hours. The job requires standing for long periods, lifting up to 40 pounds, and working with hot and cold food items. Cracker Barrel emphasizes a culture of belonging, diversity, and inclusion, offering top-notch training, diverse career paths, and competitive benefits including weekly pay, health benefits, and a 401K plan with company matching.

Strategy and Analytics Manager

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

OnSite Specialist - Rockford, IL

Company: Stryker

Location: Rockford, IL

Posted Jan 23, 2025

Server

Company: Cracker Barrel

Location: O'Fallon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a server for their Shiloh location in IL. The role involves serving guests in a fast-paced, family-friendly environment, with the mission of 'Pleasing People'. Servers keep 100% of their tips and have flexible hours. The job requires standing for long periods, lifting up to 40 pounds, and working with hot and cold food items. Cracker Barrel emphasizes a culture of belonging, diversity, and inclusion, offering top-notch training, diverse career paths, and competitive benefits including weekly pay, health benefits, and a 401K plan with company matching.

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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