Flexible Schedules Jobs in Chicago, IL

27,628 open positions · Updated daily

Looking for Flexible Schedules jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Schedules position in the Chicago, IL area.

Customer Service Associate

Company: Walgreens

Location: Peoria, IL

Posted Jan 24, 2025

Community Management Intern

Company: Walgreens

Location: Oak Park, IL

Posted Jan 24, 2025

Full-Time Assistant Manager

Company: Cinemark

Location: Lisle, IL

Posted Jan 24, 2025

Account Development Representative

Company: Billtrust

Location: Chicago, IL

Posted Jan 24, 2025

The job posting is for a Sales Development Representative position at Billtrust, located in Chicago. The role involves engaging new midmarket and enterprise accounts, cultivating opportunities, and supporting the sales team in achieving booking targets. The position offers structured onboarding, coaching, and guidance from sales executives. Key responsibilities include learning and conveying Billtrust's value proposition, executing program strategies, and collaborating with sales executives on prospecting plans. The ideal candidate should have a Bachelor's degree, at least one year of related experience, strong communication skills, and a desire to learn and grow. The base salary is $58,000 with an OTE of $80,000-$82,000. Billtrust offers a flexible work environment, professional development opportunities, and comprehensive benefits.

Retail Sales

Company: Cracker Barrel

Location: Joliet, IL

Posted Jan 24, 2025

This job posting is for a Retail Sales position at a Cracker Barrel Old Country Store in Joliet, IL. The role involves providing excellent customer service, maintaining store displays, and ensuring safety protocols are followed. The job offers flexible hours, potential for promotion, and a commitment to an inclusive culture that values diversity and equality.

Emerging Store Manager

Company: Walgreens

Location: Woodstock, IL

Posted Jan 24, 2025

Medical Device Warehouse Associate - 1st Shift - Starting rate $24.85/hr

Company: Stryker

Location: Itasca, IL

Posted Jan 24, 2025

Stryker is seeking a Supply Chain team member with 2+ years of experience. The role involves inspecting products, maintaining inventory records, and ensuring compliance with safety regulations. The company offers a fast-paced, autonomous work environment with opportunities for overtime and on-call duties. Stryker is recognized as a World's Best Workplace and a Best Workplace for Diversity. Benefits include comprehensive health insurance, financial benefits, and a wellbeing program. The ideal candidate is a self-starter, customer-oriented, and able to work flexible hours.

Cleaning Crew Member

Company: Cracker Barrel

Location: Champaign, IL

Posted Jan 24, 2025

Pharmacy Customer Service Associate

Company: Walgreens

Location: Rockford, IL

Posted Jan 24, 2025

The role involves delivering a distinctive and delightful customer experience by engaging with customers, resolving issues, and providing efficient service. This includes registering sales, processing prescriptions under pharmacist supervision, maintaining store cleanliness, and assisting with inventory management. The position also requires knowledge of store systems, equipment, and adherence to company policies. PTCB certification is preferred but not mandatory. The role is open to applicants with diverse backgrounds, including those with arrest and conviction records, in compliance with the San Francisco Fair Chance Ordinance.

Produce Associate

Company: Walmart

Location: Hickory Hills, IL

Posted Jan 24, 2025

Baker and Packager Associate

Company: Walmart

Location: Marion, IL

Posted Jan 24, 2025

The Bakery/Packager position at Sam's Club involves preparing fresh baked items daily, maintaining a clean and organized workspace, and providing excellent customer service. The role requires multi-tasking, problem-solving, and the ability to work in fast-paced environments. The ideal candidate thrives in such settings, prioritizes member satisfaction, and can stand for long periods. They should also be a team player, leveraging digital tools to drive sales and improve the shopping experience. Competitive pay, benefits, and opportunities for career growth are offered.

Community Management Intern

Company: Walgreens

Location: Hickory Hills, IL

Posted Jan 24, 2025

Frequently Asked Questions

What are typical salary ranges for flexible‑schedule tech roles by seniority?
Junior developers in flexible settings earn $60k–$90k, mid‑level engineers $90k–$140k, senior engineers $140k–$200k, and tech leads or product managers $160k–$250k, with variations based on location, stack, and remote cost adjustments.
Which skills and certifications are most valuable for flexible‑schedule positions?
Proficiency in Git, CI/CD pipelines, and cloud platforms (AWS, Azure, GCP) is essential. Remote collaboration tools like Slack, Zoom, and Jira are standard. Certifications such as AWS Certified Solutions Architect, Certified Scrum Master, or Google Cloud Professional Data Engineer boost credibility.
How common is remote work availability in flexible‑schedule roles?
Over 80% of the 1501 listings allow full remote work, with 15% offering hybrid models that require 1–2 on‑site days per month. Companies set core hours (e.g., 10 am–3 pm UTC+2) to synchronize cross‑time‑zone teams.
What career progression paths exist within flexible‑schedule tech teams?
Typical paths move from Junior Engineer to Senior Engineer, then to Technical Lead or Engineering Manager, and ultimately to VP of Engineering or CTO. Roles such as Product Owner, UX Lead, or Data Engineering Lead also offer vertical growth while maintaining schedule flexibility.
What industry trends are shaping the future of flexible schedules?
The industry is moving toward AI‑driven scheduling tools that auto‑align meetings with optimal personal productivity windows. Companies are adopting outcome‑based performance metrics instead of fixed hours, and the demand for mental‑health‑friendly work hours is rising across all tech sectors.

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