Flexible Schedules Jobs in Chicago, IL

27,633 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.

Pharmacy Customer Service Associate

Company: Walgreens

Location: Peoria, IL

Posted Jan 21, 2025

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.

Courtesy Clerk/Grocery Bagger

Company: Kroger

Location: Chicago, IL

Posted Jan 22, 2025

Bakery/Deli Clerk

Company: Kroger

Location: Springfield, IL

Posted Jan 22, 2025

The job description is for a Grocery Clerk (Bakery/Deli) role, focusing on preparing items, offering product samples, and ensuring customer satisfaction. Responsibilities include using bakery equipment, maintaining product quality, and adhering to food safety regulations. The ideal candidate should have customer service skills, stress management abilities, and basic math knowledge. Previous bakery or retail experience is beneficial. Kroger, the employer, emphasizes its commitment to employees' well-being, offering comprehensive benefits such as healthcare coverage, flexible scheduling, and tuition reimbursement.

Grocery Clerk

Company: Kroger

Location: Peoria, IL

Posted Jan 22, 2025

The job description is for a Grocery Clerk at Kroger, a large national grocer. The role involves providing excellent customer service, maintaining a clean and safe environment, assisting in meeting sales and profit goals, and adhering to company values. Responsibilities include helping customers discover new products, informing them of specials, checking product quality, stocking shelves, and reporting discrepancies. The ideal candidate should have customer service skills, effective communication, and basic math knowledge. Kroger offers comprehensive benefits including healthcare, flexible scheduling, emotional and financial support, associate discounts, tuition reimbursement, and growth opportunities.

Courtesy Clerk/Grocery Bagger

Company: Kroger

Location: Villa Park, IL

Posted Jan 22, 2025

The job description outlines the responsibilities of a Courtesy Clerk/Grocery Bagger, including providing excellent customer service, maintaining a safe and clean environment, and adhering to company policies and procedures. The role requires strong communication skills, ability to handle stressful situations, and a passion for food and people. Mariano's offers comprehensive benefits, including healthcare coverage, flexible scheduling, and tuition reimbursement.

Cashier

Company: Kroger

Location: Northbrook, IL

Posted Jan 22, 2025

MEAT/JOURNEYMAN

Company: Kroger

Location: Hoffman Estates, IL

Posted Jan 22, 2025

The job description involves performing general production work, maintaining and operating the department, and demonstrating the company's core values. Responsibilities include responding to customer needs, accurately updating temperature logs, training associates, and maintaining a clean, safe, and organized work environment. The role requires effective communication skills, teamwork, and the ability to handle stressful situations professionally. Desired qualifications include meat work experience, dependability, and knowledge of employment laws. The company, Mariano's, offers comprehensive benefits including healthcare coverage, flexible scheduling, emotional and financial support, associate discounts, tuition reimbursement, and growth opportunities.

Grocery Clerk

Company: Kroger

Location: Oakbrook, IL

Posted Jan 22, 2025

The job description outlines responsibilities for a Grocery Clerk at Mariano's, a Kroger company. Key duties include creating a positive customer experience, maintaining a clean and safe environment, assisting in sales and profit goals, and ensuring product freshness. The role involves customer service, product knowledge, and adherence to food safety regulations. The company values respect, honesty, integrity, diversity, inclusion, and safety. Qualifications include customer service skills, stress management, effective communication, and basic math. Benefits include healthcare coverage, flexible scheduling, emotional and financial support, associate discounts, tuition reimbursement, and growth opportunities.

Sales Enablement Specialist

Company: SpotHero

Location: Chicago, IL

Posted Jan 22, 2025

SpotHero, a rapidly growing parking industry technology company, is seeking a Sales Enablement Specialist. The role involves enhancing the sales organization's effectiveness by creating solutions for onboarding, training, and content management. The ideal candidate will have 2+ years of experience in Sales, Marketing, or Sales Enablement, proficiency in LMS and CMS platforms, and excellent communication skills. The company offers a unique career opportunity with excellent benefits, flexible PTO, and a supportive work environment. The position is based in Chicago, Illinois, with a requirement to work in the office once a week.

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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