Flexible Schedules Jobs in Chicago, IL

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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.

Part-Time District Sales Associate

Company: Oishii

Location: Chicago, IL

Posted Dec 20, 2024

The job involves growing and selling vertically farmed, pesticide-free strawberries. The District Sales Associate (DSA) will spend 90% of their time in the field, primarily in stores, and 10% on office administrative tasks. The DSA will maintain merchandising standards, complete reports, and develop relationships with stakeholders. The role requires quick prioritization, effective communication, and the ability to remove obstacles. It is a part-time role with varying hours and schedules.

Director - Cyber Strategy & Analytics

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Dec 20, 2024

The text describes a job description for a Director Cyber Strategy and Analytics role at McDonald's. The role involves leading the future development of the company's cybersecurity strategy, implementing tools and processes, and working closely with various teams to analyze and report on cybersecurity risk. The position requires strong leadership, strategic thinking, and the ability to work with multifunctional teams. The expected salary range is $168,350 to $218,860.

Integrated Marketing Manager

Company: Hitachi Solutions America

Location: Chicago, IL

Posted Dec 20, 2024

Hitachi Solutions is a global Microsoft solutions integrator with a focus on developing and delivering industry-specific solutions to support clients in their business transformation goals. The company has a long history, strong financial strength, and international presence, with a passion for innovation and a strategic relationship with Microsoft. They are seeking a high-performing B2B marketer to execute integrated campaigns and marketing activities.

Pharmacy Customer Service Associate

Company: Walgreens

Location: Carbondale, IL

Posted Dec 20, 2024

The job description involves delivering a distinctive and delightful customer experience, including greeting customers, offering assistance, resolving issues, and ensuring positive interactions. The role also includes operating a cash register, processing prescriptions under pharmacist supervision, maintaining store cleanliness, and handling inventory. The employee is expected to adhere to company policies, maintain knowledge of healthcare and pharmacy, and complete necessary training and certifications. Fluency in English, flexibility for various shifts, and good math and computer skills are preferred.

Drive with Lyft - Features made for women + enby drivers

Company: Lyft

Location: Rock Island, IL

Posted Dec 20, 2024

Lyft is offering a new driver promotion in Davenport, where new drivers can earn $400 by providing 40 rides within 7 days. The company is also introducing the Women+ Connect feature, aimed at enhancing the driving experience for women and nonbinary drivers. Lyft is portrayed as a flexible earning opportunity, providing drivers with control over their schedules and earnings. No prior experience is required, making it an attractive option for part-time, full-time, or seasonal work.

SAS in Jewel – Part Time Retail Merchandiser

Company: Lee Company

Location: Villa Park, IL

Posted Dec 20, 2024

SAS Retail Services offers a job as a Reset Merchandiser with flexible Monday-Friday work, paid training, and growth opportunities. The role involves product movement and tracking, but also allows for independence and customization of benefits.

Customer Service Associate

Company: Walgreens

Location: Springfield, IL

Posted Dec 20, 2024

The role involves delivering a distinctive and delightful customer experience, providing courteous and efficient checkout services, engaging customers, resolving issues, and sharing best practices. The employee is expected to maintain cleanliness, implement asset protection procedures, comply with laws, construct displays, and handle various store systems and equipment. They also provide customer service in the photo area and assume web pick-up responsibilities. Fluency in English is required, and six months of retail experience is preferred.

Staff Accountant II (Hybrid: Onsite and Remote)

Company: US Foods

Location: Rosemont, IL

Posted Dec 20, 2024

The Staff Accountant II role involves end-to-end process and analysis, preparing accounting/tax and reporting activities, and collaborating with corporate office functions. The position requires skills in prioritization, organization, multi-tasking, attention to detail, communications, analytical, problem-solving, independent thinking, and team participation.

Pharmacy Customer Service Associate

Company: Walgreens

Location: Chicago, IL

Posted Dec 20, 2024

The job description involves delivering a distinctive and delightful customer experience, including greeting customers, offering assistance, resolving issues, and ensuring positive interactions. The role also includes operating a cash register, processing prescriptions under pharmacist supervision, maintaining store cleanliness, and handling inventory. The employee is expected to adhere to company policies, maintain knowledge of healthcare and pharmacy developments, and complete necessary training and certifications.

Business Office Associate - Part Time

Company: CarMax

Location: Northbrook, IL

Posted Dec 20, 2024

CarMax is seeking a Business Office Associate to provide exceptional customer service in a fast-paced environment. The role involves assisting store personnel, processing paperwork, and managing multiple pay types. The position requires ability to read, interpret, and transcribe data, as well as prioritize and multi-task in a deadline-oriented environment.

Pharmacy Cashier

Company: Walgreens

Location: Northbrook, IL

Posted Dec 20, 2024

The role involves delivering a distinctive and delightful customer experience, including greeting customers, offering assistance, resolving issues, and sharing best practices. The individual operates cash registers, processes transactions, and maintains store cleanliness and merchandise. They also handle pharmacy systems, implement asset protection procedures, and ensure compliance with regulated product laws. The role requires flexibility in scheduling and preferred experience in retail or with Walgreens. Training and personal development are emphasized, with compensation ranging from $16 to $18 hourly.

Premium Auditor

Company: RLI Insurance Company

Location: Peoria, IL

Posted Dec 20, 2024

RLI is a Glassdoor Best Places to Work company with a strong financial track record, stellar reputation as an excellent underwriting company, and a culture that values culture and validation of reputation. The company offers a Total Rewards program that includes financial incentives, work-life benefits, health and wellness benefits, and employee stock ownership plan. The company encourages professional development and diversity and inclusion.

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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