Flexible Schedules Jobs in Chicago, IL

27,629 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: Chicago, IL

Posted Jan 23, 2025

Cook

Company: Cracker Barrel

Location: O'Fallon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a Cook to join their kitchen team. The role involves preparing a full menu of Southern favorites using Cracker Barrel's recipes and methods. The Cook will ensure high standards of professional cooking, quality, safety, cleanliness, and hospitality. Flexible hours are available, and there are opportunities for promotion and continued development. The company values diversity, equity, and inclusion, and offers a culture of belonging, top-notch training, diverse career paths, and competitive pay and benefits.

Customer Service Associate

Company: Walgreens

Location: Downers Grove, IL

Posted Jan 23, 2025

The text describes a job role that involves delivering a distinctive and delightful customer experience. The responsibilities include engaging customers, resolving issues, and providing efficient checkout service. The role also involves maintaining store cleanliness, implementing asset protection procedures, and ensuring compliance with regulated product laws. The job requires fluency in English and a flexible schedule, including evenings and weekends. Preferred qualifications include prior retail experience and familiarity with Walgreens. The role offers a salary range of $15 - $17.5 per hour.

Community Management Intern

Company: Walgreens

Location: Orland Park, IL

Posted Jan 23, 2025

The job involves providing an extraordinary customer experience in a retail store setting, engaging customers, resolving issues, and modeling customer service best practices. Responsibilities include operating cash registers, managing inventory, maintaining store cleanliness, and ensuring compliance with regulations. The role also involves learning from store managers, competitors, and customers, and participating in team challenges. Basic qualifications include being a student in the senior year towards a Bachelor's degree, fluency in English, and flexibility for various shifts.

Retail Sales

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

H&M Sales Associate

Company: H&M

Location: Schaumburg, IL

Posted Jan 23, 2025

Part-Time Assistant Manager

Company: Cinemark

Location: Lisle, IL

Posted Jan 23, 2025

Server

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a server for their Effingham location. The role involves serving guests in a fast-paced, family-friendly environment, with the mission of 'Pleasing People'. Servers keep 100% of their tips and have flexible hours. The job requires standing for long periods, lifting up to 40 pounds, and working with hot and cold food items. Cracker Barrel emphasizes a culture of belonging, diversity, and inclusion, offering top-notch training, diverse career paths, and competitive benefits including weekly pay, health benefits, and a 401K plan with company matching.

OnSite Specialist - Rockford, IL

Company: Stryker

Location: Rockford, IL

Posted Jan 23, 2025

Server

Company: Cracker Barrel

Location: O'Fallon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a server for their Shiloh location in IL. The role involves serving guests in a fast-paced, family-friendly environment, with the mission of 'Pleasing People'. Servers keep 100% of their tips and have flexible hours. The job requires standing for long periods, lifting up to 40 pounds, and working with hot and cold food items. Cracker Barrel emphasizes a culture of belonging, diversity, and inclusion, offering top-notch training, diverse career paths, and competitive benefits including weekly pay, health benefits, and a 401K plan with company matching.

Wealth Management-Chicago-Administrative Assistant- Support

Company: Goldman Sachs

Location: Chicago, IL

Posted Jan 23, 2025

The Goldman Sachs Group, Inc., a renowned global investment firm, is seeking an administrative professional for a senior role in Chicago. The position involves providing complex support to executives, coordinating meetings, managing travel, and handling sensitive information. The ideal candidate should possess excellent communication skills, high attention to detail, and strong organizational abilities. A minimum of 3-5 years of experience is preferred. The salary range is $70,000-$110,000, with potential for a discretionary bonus. Goldman Sachs offers competitive benefits and a positive work environment.

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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