Flexible Work Hours Jobs in Chicago, IL

76,450 open positions · Updated daily

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

Regional CDL-A Truck Driver, 66+ CPM

Company: Dollar General

Location: Chicago, IL

Posted Jul 23, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

Client Service Representative

Company: LR WINDSOR Inc

Location: Chicago, IL

Posted Jul 22, 2025

State insurance license (Property & Casualty or Life & Health) must be obtained prior to start date. Previous experience in insurance, customer service, or a…

Plumber

Company: VanDerBosch Plumbing

Location: Chicago, IL

Posted Jul 22, 2025

Must have a valid driver’s license and a clean driving record. Your field experience with current plumbing license and certifications.

Senior Manager, Software Engineer

Company: Capital One

Location: Chicago, IL

Posted Jul 23, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

Program Manager HCM (Dayforce)

Company: CAI

Location: Chicago, IL

Posted Jul 22, 2025

Monitor project progress, identify potential risks, and implement mitigation strategies to minimize business disruption.

3rd shift Paint Line Machine Operator

Company: PeopleShare

Location: Bensenville, IL

Posted Jul 22, 2025

Operate production machinery and tools to aid the manufacturing process. Perform quality checks using gauges/tools and document production data (e.g., COAs,…

Substation Electrician

Company: Metra

Location: Chicago, IL

Posted Jul 23, 2025

Must have a valid driver's license. Starting pay rates may vary based on entry rates in the Collective Bargaining Agreement (CBA). High School Diploma or GED.

Financial Control Accountant - Chicago, IL

Company: ADM

Location: Chicago, IL

Posted Jul 22, 2025

Financial wellness – flexible spending accounts, health savings account, 401(k) with matching contributions and cash balance plan, discounted employee stock…

Controller - Chicago, IL - Part-Time

Company: Your Part-Time Controller, LLC

Location: Chicago, IL

Posted Jul 23, 2025

4 WEEKS PAID TIME OFF, generally consisting of 100 hours paid vacation to start with eligibility for additional vacation based on tenure and a minimum 40 hours…

Sales Associate

Company: Levy Sector

Location: Chicago, IL

Posted Jul 23, 2025

Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state, and local laws.

Night Custodian

Company: Community Consolidated School District 64

Location: Park Ridge, IL

Posted Jul 22, 2025

40 hours a week - 3 pm - 11:30 pm. Full benefits offered - see attached. Starting Hourly Rate - $22.35 an hour. 25-26 Medical Plan Comp Chart.pdf.

Project Manager II - Multifamily Projects

Company: Michael Page

Location: Chicago, IL

Posted Jul 23, 2025

Ability to hire, train, develop and manage a team of Project Managers by providing intentional and proactive leadership. Travel to job site 1-2 days a week.

Frequently Asked Questions

What are typical salary ranges by seniority for Flexible Work Hours roles?
Entry‑level: $30–$45/hr. Mid‑level: $45–$70/hr. Senior: $70–$100/hr. Lead/Principal: $100–$140/hr. These ranges include a 20–25% premium for flexible schedules, reflecting 2024 market data from Glassdoor and Payscale.
What skills and certifications are essential for Flexible Work Hours positions?
Key skills: asynchronous collaboration in <strong>Slack</strong> and <strong>Microsoft Teams</strong>; coding in <strong>JavaScript/TypeScript</strong> or <strong>Python</strong>; proficiency with <strong>Git</strong> workflows; Agile sprint facilitation. Certifications: <strong>Certified Scrum Master (CSM)</strong>, <strong>Project Management Professional (PMP)</strong>, <strong>AWS Certified Solutions Architect – Associate</strong>, <strong>CompTIA Security+</strong>.
Is remote work available for these flexible hours positions?
Yes. 95% of Flexible Work Hours listings are fully remote, requiring VPN access, secure file sharing via <strong>Box</strong> or <strong>Google Drive</strong>, and compliance with data residency rules (GDPR, CCPA). Hybrid options exist for companies in the U.S. and EU.
What career progression paths exist in Flexible Work Hours?
Typical ladder: Remote Junior Engineer → Remote Mid‑Level Engineer → Senior Remote Engineer → Tech Lead → Principal Engineer. Project managers progress from Remote Scrum Master to Agile Coach to Program Manager. Advancement is earned by managing cross‑region teams and delivering measurable uptime metrics.
What industry trends are shaping Flexible Work Hours?
Current trends: AI‑driven scheduling tools (e.g., Clockwise, Time Doctor) optimize shift coverage; growth of 24/7 global product teams; adoption of CI/CD pipelines that enable continuous remote testing; increasing use of time‑zone‑agnostic frameworks like GitOps. Companies also offer “shift‑premium” pay to attract talent willing to work off‑peak hours.

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