Flexible Schedule Jobs in Chicago, IL

34,512 open positions · Updated daily

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

Dishwasher

Company: Cracker Barrel

Location: Springfield, IL

Posted Jan 22, 2025

Entry-Level Sales Consultant - Cargo (Chicago) | Training in New York

Company: Air Charter Service

Location: Chicago, IL

Posted Jan 22, 2025

Air Charter Service is seeking an experienced sales professional to build relationships with potential customers, maintain existing ones, and manage charter bookings. The role involves outbound sales calls, visits, and presenting bespoke quotes. The company offers award-winning training, international travel opportunities, and a dynamic work environment. The compensation package includes a base salary, uncapped commission, and comprehensive benefits.

Baker and Packager Associate

Company: Walmart

Location: Oak Park, IL

Posted Jan 22, 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.

Product Marketing Manager (hybrid)

Company: Peapod Digital Labs

Location: Chicago, IL

Posted Jan 22, 2025

Peapod Digital Labs, an Ahold Delhaize USA company, is seeking a Product Marketing Manager. The role involves developing commercial strategies, driving growth for media channels, and supporting the Strategy & Operations Lead in growing brand equity. The ideal candidate should have 5-7 years of experience in retail, IT, or similar projects, preferably involving media or marketing channels. They should be comfortable bridging the gap between product and sales, and have strong communication skills. Peapod Digital Labs values diversity, equity, inclusion, and offers comprehensive benefits.

Host

Company: Cracker Barrel

Location: O'Fallon, IL

Posted Jan 22, 2025

The job posting for a Host at Cracker Barrel Old Country Store in Shiloh, IL, emphasizes a welcoming and friendly environment. The role involves greeting guests, managing seating, and potentially growing within the company. Cracker Barrel highlights its commitment to diversity, equity, and inclusion, offering top-notch training, diverse career paths, and competitive benefits. The company fosters a culture of belonging, encouraging employees to be themselves and celebrate differences.

Entry-level Private Jet Sales Consultant (Chicago)

Company: Air Charter Service

Location: Chicago, IL

Posted Jan 22, 2025

Air Charter Service (ACS) is a leading aircraft charter company seeking a Private Jet Sales Consultant for their Chicago office. The role involves building client relationships, managing the sales cycle, and ensuring client satisfaction. ACS offers a dynamic work environment, international travel opportunities, and competitive compensation. The company values excellent communication skills, adaptability, and a client-facing approach.

Customer Service Associate

Company: Walgreens

Location: Villa Park, IL

Posted Jan 22, 2025

Produce Associate

Company: Walmart

Location: Rockford, IL

Posted Jan 22, 2025

This job posting is for a produce team member at Sam's Club. The role involves ensuring the availability, cleanliness, and freshness of produce, prioritizing member satisfaction, and providing excellent customer service. The ideal candidate should have experience with produce, be comfortable with change, and possess strong communication skills. Key responsibilities include maintaining a positive attitude, providing exceptional customer service, stocking merchandise, and maintaining inventory. The position offers competitive pay, benefits including health, financial, and time-off benefits, and opportunities for career growth. The hourly wage range is $16.00 to $23.00.

Pharmacy Intern

Company: Walgreens

Location: Homewood, IL

Posted Jan 22, 2025

Community Management Intern

Company: Walgreens

Location: Oak Park, IL

Posted Jan 22, 2025

Dishwasher

Company: Cracker Barrel

Location: Rockford, IL

Posted Jan 22, 2025

The job posting for a Dishwasher at Cracker Barrel Old Country Store in Rockford, 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.

Host

Company: Cracker Barrel

Location: Decatur, IL

Posted Jan 22, 2025

The job posting for a Host at Cracker Barrel Old Country Store in Decatur, IL, emphasizes a welcoming and friendly environment. The role involves greeting guests, managing seating, and ensuring a positive dining experience. The company values diversity, equity, and inclusion, and offers a range of benefits including competitive pay, flexible schedules, health benefits, and opportunities for career growth. The training program, PAR, is designed to help employees grow and succeed, with potential for pay increases. The company culture is described as a 'Family' atmosphere, where employees are encouraged to be themselves and celebrate differences.

Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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