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.

Associate Category Manager

Company:

Location: Gurnee, IL

Posted Jan 24, 2025

Uline, a family-owned company, is seeking an Associate Category Manager for its Corporate Headquarters in Pleasant Prairie, WI. The role involves managing a product line, researching and sourcing new products, visiting vendors, and attending tradeshows. The ideal candidate should have a Bachelor's degree, 2-5 years of experience in Product Management, Supply Chain, or Marketing, and proficiency in Microsoft Office. Benefits include comprehensive insurance, 401(k) with employer match, bonus programs, paid holidays, and a Tuition Assistance Program. Uline offers on-site amenities like a café, fitness center, and walking trails.

Microsoft 365 System Administrator

Company:

Location: Northbrook, IL

Posted Jan 24, 2025

IT Infrastructure Architect

Company:

Location: Gurnee, IL

Posted Jan 24, 2025

Uline, a family-owned company, is offering a position for an IT Infrastructure Architect with a salary range of $121,000 to $185,000 per year. The role involves architecting, designing, and delivering highly available, reliable, and cost-effective hosting solutions. The ideal candidate should have a Bachelor's degree, 8+ years of experience with VMware, SAN, Windows, and Citrix, and excellent communication skills. Benefits include comprehensive insurance coverage, a 401(k) plan with employer match, multiple bonus programs, and various perks like an on-site café and fitness center.

Associate Product Manager

Company:

Location: Hickory Hills, IL

Posted Jan 24, 2025

Uline, a family-owned company, is seeking an Associate Product Manager for its Corporate Headquarters in Pleasant Prairie, WI. The role involves managing a product line, researching and sourcing new products, visiting vendors, and attending tradeshows. The ideal candidate should have a Bachelor's degree, 2-5 years of experience in Product Management, Supply Chain, or Marketing, and proficiency in Microsoft Office. Benefits include comprehensive insurance, 401(k) with employer match, bonus programs, paid holidays, and generous paid time off. Uline offers additional perks like an on-site café, fitness center, and walking trails.

Packaging Engineer Manager

Company:

Location: Mundelein, IL

Posted Jan 24, 2025

IT Infrastructure Architect

Company:

Location: Deerfield, IL

Posted Jan 24, 2025

Uline, a family-owned company, is offering an IT Infrastructure Architect position with a salary range of $121,000 to $185,000 per year. The role involves architecting, designing, and delivering highly available, reliable, and cost-effective hosting solutions. The ideal candidate should have a Bachelor's degree, 8+ years of experience with VMware, SAN, Windows, and Citrix, and excellent communication skills. Benefits include comprehensive insurance coverage, a 401(k) with employer match, multiple bonus programs, and employee perks like an on-site café and fitness center.

IT Infrastructure Architect

Company:

Location: Lake Bluff, IL

Posted Jan 24, 2025

Uline, a family-owned company, is offering an IT Infrastructure Architect position with a salary range of $121,000 to $185,000 per year. The role involves architecting, designing, and delivering highly available, reliable, and cost-effective hosting solutions. The ideal candidate should have a Bachelor's degree and 8+ years of experience with VMware, SAN, Windows, and Citrix. Benefits include comprehensive insurance coverage, a 401(k) plan with employer match, multiple bonus programs, and employee perks like an on-site café and fitness center.

Target Security Specialist

Company: Target

Location: Chicago, IL

Posted Jan 24, 2025

Planning and Inventory Manager

Company:

Location: Mundelein, IL

Posted Jan 24, 2025

Insurance Agent

Company: COUNTRY Financial

Location: DeKalb, IL

Posted Jan 24, 2025

COUNTRY Financial is seeking insurance sales agents dedicated to building customer networks, finding prospects, and ensuring their financial security. The company offers competitive compensation, benefits, and comprehensive training. The ideal agent is proactive, transparent, and customer-focused, with the ability to educate and build trust. While not required, obtaining necessary insurance licenses is essential. COUNTRY Financial is a respected, growing organization committed to customer service and diversity.

EHS Manager

Company: Eaton

Location: Glendale Heights, IL

Posted Jan 24, 2025

Software Development Team Lead - Java

Company:

Location: Deerfield, IL

Posted Jan 24, 2025

Uline, a family-owned company, is seeking a Software Development Team Lead with 8+ years of experience in Java, Angular, or JavaScript. The role involves leading a team of 3-5 developers, guiding them in designing and developing complex applications. The position offers comprehensive benefits including health insurance, 401(k) with 6% employer match, multiple bonus programs, paid holidays, generous paid time off, and a Tuition Assistance Program. Uline provides on-site amenities like a café, fitness center, and walking trails. The company is North America's leading distributor of shipping, industrial, and packaging materials with over 9,000 employees.

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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