Flexible Schedule Jobs in Chicago, IL

Positions 34,512 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.

Sr. Accountant - Close and Consolidations

Company: Northern Trust Corp.

Location: Chicago, IL

Posted Sep 19, 2025

Acts as a key contact for various internal and external partners with the ability to communicate succinctly and interpret financial results in non-technical…

Special Education Teacher

Company: Betty Shabazz International Charter Schools

Location: Chicago, IL

Posted Sep 19, 2025

Evidence classroom management practices that fosters respects as well as affirm and inspire students to become self-confident, independent, successful learners,…

Cybersecurity Analyst

Company: Delan Associates, Inc

Location: Lemont, IL

Posted Sep 18, 2025

The contractor shall adhere to all policies and procedures of the ANL Computer Protection Program, must not bypass any procedures established to protect data,…

Built Environment & Sustainability Project Manager

Company: The Academy for Global Citizenship

Location: Chicago, IL

Posted Sep 19, 2025

AGC’s new learning hub will provide critically needed access to tuition-free early childhood learning, high quality K-8 public education, health care and mental…

Cyber Risk Analyst

Company: Delan Associates, Inc

Location: Lemont, IL

Posted Sep 18, 2025

For the candidate within driving distance of the Lab, there may be rare times to be onsite for in-person meetings, assessments, or presentations.

Construction Worker

Company: EcoBuild and Green Attic

Location: Mount Prospect, IL

Posted Sep 19, 2025

Basic HVAC, plumbing, or electrical experience. Own hand and power tools. Trim carpentry (baseboards, doors, casing, cabinet installation — including coping/…

CNC Machinist III, 1st shift

Company: Regal Rexnord

Location: Downers Grove, IL

Posted Sep 19, 2025

Person’, which includes U.S. citizens, U.S. nationals, U.S. permanent residents, individuals granted asylum in the United States, and refugees in the United…

Retail Customer Service & Sales Associate

Company: Vici Marketing, Inc

Location: Burr Ridge, IL

Posted Sep 19, 2025

Operate the cash register efficiently and accurately while handling transactions. Basic math skills for handling transactions and cash management.

Experienced Commercial Painter

Company: Southwest Coating Services

Location: Bridgeview, IL

Posted Sep 22, 2025

Reliable vehicle, valid driver's license and proof of insurance. 401K matching after 6 months of employment. Wallcovering installation a plus, but not required.

Staff Accountant

Company: IPS Corporation

Location: Downers Grove, IL

Posted Sep 20, 2025

Bachelor's degree in accounting, finance, or a related field. Capitalize CWIP based on analysis and ensure proper classification. 401(k) with Company Match.

Bilingual CSR Mobile Sales Multiple Positions and Locations!

Company: PeopleShare

Location: Chicago, IL

Posted Sep 18, 2025

PeopleShare provides equal opportunities to all employees and applicants for employment without regard to race, religion, color, age, sex, national origin,…

Armed Driver Cash Transport - FOID Required

Company: GardaWorld Cash

Location: Broadview, IL

Posted Sep 19, 2025

21 years of age or older with a valid and clean driver’s license. We provide our clients with solutions in every phase of their cash supply chain, including…

Frequently Asked Questions

What are typical salary ranges by seniority for flexible schedule tech roles?
Entry‑level (0‑2 years) $70k‑$95k; Mid‑level (2‑5 years) $95k‑$135k; Senior (5‑10 years) $135k‑$180k; Lead/Principal (10+ years) $180k‑$250k. These ranges adjust for region and industry, with remote‑first firms often offering cost‑of‑living adjustments.
What skills and certifications are required for flexible schedule positions?
Core skills: proficiency with Git, GitHub/GitLab, Slack, JIRA, Asana, and Zoom for asynchronous collaboration. Certifications: AWS Certified Solutions Architect, Google Cloud Professional Cloud Architect, Certified ScrumMaster (CSM), Project Management Professional (PMP), and Google UX Design Certificate are highly valued.
Is remote work available for flexible schedule roles?
Yes—most flexible schedule positions are fully remote. Companies such as GitLab, Automattic, and Atlassian provide 100% remote options, while others offer hybrid models with flexible days. Remote‑first culture is a standard expectation across this category.
What career progression paths exist in flexible schedule tech roles?
Typical paths: Junior Engineer → Mid‑level Engineer → Senior Engineer → Staff Engineer → Principal Engineer or Product Manager → Senior PM → Lead PM → Head of Product. Continuous learning, mentorship, and internal promotion are key, with many firms investing in skill development and certifications.
What industry trends are shaping flexible schedule jobs?
Key trends include the rise of remote‑first companies, AI‑powered collaboration tools like Notion AI and Slack GPT, increased demand for asynchronous communication expertise, higher adoption of flexible work policies in Fortune 500 firms, and a growing freelance economy for hourly remote specialists.

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