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.

Emerging Store Manager

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

Pharmacy Customer Service Associate

Company: Walgreens

Location: Galesburg, IL

Posted Jan 23, 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 developments, and complete necessary training and certifications.

SR. Counsel, Digital Products, Data Analytics & Intellectual Property

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

The role involves providing legal advice and recommendations to executives and management across various business units, with a focus on technology transactions, product counseling, intellectual property, privacy, and security laws. The individual will structure and negotiate commercial agreements, collaborate with cross-functional teams, and maintain an understanding of Walgreens' digital product offerings and business goals. They will also leverage their legal expertise to mitigate business risks and contribute to financial decisions. The ideal candidate should have a Juris Doctorate, at least 5 years of post-bar legal experience, and Illinois bar membership.

Sports Director

Company: Area Scouts

Location: Chicago, IL / Remote

Posted Jan 23, 2025

Area Scouts is expanding its team and seeking experienced, self-motivated individuals with a background in coaching or playing various sports such as baseball, basketball, softball, football, volleyball, and lacrosse. The role involves working with youth athletes, maintaining relationships with local and national sports organizations, and conducting evaluations. The company emphasizes diversity, inclusion, and equal opportunity, and offers flexible full-time, part-time, temporary, internship, and contract positions with salary based on experience.

Retail Sales

Company: Cracker Barrel

Location: Bloomington, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a Retail Sales team member in Bloomington, IL. The role involves managing the retail shop, providing excellent guest service, and maintaining stock. The position offers flexible hours, potential for promotion, and comprehensive training. The company values diversity, equity, and inclusion, and provides a culture of belonging, top-notch training, diverse career paths, and competitive benefits. The job requires the ability to stand for long periods, lift up to 40 pounds, and work with various food items.

Senior Staff Regulatory Specialist, Pharmaceuticals

Company: Stryker

Location: Cary, IL

Posted Jan 23, 2025

Stryker is seeking a Senior Staff Regulatory Affairs Specialist for a hybrid role in Cary, IL. The ideal candidate should be detail-oriented, collaborative, and business-oriented. They will prepare and author FDA INDs and NDAs, assess regulatory reporting mechanisms, and provide guidance to other departments. Stryker, a global medical technology leader, offers innovative products and services in various fields, impacting over 130 million patients annually. Benefits include comprehensive health and financial packages.

Dishwasher

Company: Cracker Barrel

Location: Decatur, IL

Posted Jan 23, 2025

The job posting for a Dishwasher at Cracker Barrel Old Country Store in Decatur, IL emphasizes a positive work environment. The role involves working closely with kitchen and dining room teams to ensure guest satisfaction. The company values its employees, offering a culture of belonging, top-notch training, diverse career paths, and competitive pay and benefits. Cracker Barrel is committed to diversity, equity, and inclusion, and explicitly states that racism has no place in their workplace.

Drive with Lyft - Features made for women + enby drivers

Company: Lyft

Location: Chicago, IL

Posted Jan 23, 2025

Lyft is offering a $700 bonus for new drivers in Chicago who complete 140 rides within the first 30 days. The company is also launching the Women+ Connect feature, aimed at enhancing the driving experience for women and nonbinary drivers. Lyft provides flexibility, with no hourly requirements and the option to cash out any time with Express Pay. Drivers can earn extra income, making it a great alternative to part-time, full-time, or seasonal jobs. No prior experience is needed, but transportation industry experience is beneficial.

Drive with Lyft - No Experience Needed

Company: Lyft

Location: Chicago, IL

Posted Jan 23, 2025

Lyft is offering a $700 bonus for new drivers in Chicago who complete 140 rides within the first 30 days. The company is also launching the Women+ Connect feature, aimed at enhancing the driving experience for women and nonbinary drivers. Lyft provides flexibility, with no hourly requirements and the option to cash out any time with Express Pay. Drivers can earn extra income, making it a great alternative to part-time, full-time, or seasonal jobs. No prior experience is needed, but transportation industry experience is beneficial.

Pharmacy Customer Service Associate

Company: Walgreens

Location: Carbondale, IL

Posted Jan 23, 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.

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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