Flexible Work Arrangements Jobs in Chicago, IL

74,517 open positions · Updated daily

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

Experienced Fine Jewelry Sales Professional

Company: Sidney Garber

Location: Chicago, IL

Posted May 20, 2025

Manage relationships with established clients, new sales leads and prospects through the use of detailed clienteling and CRM tools.

Specialist Customer Experience

Company: Lakeshore Recycling Systems LLC

Location: Rosemont, IL

Posted May 19, 2025

Handle incoming calls (orders, inquiries, complaints, etc.) and direct calls for further problem resolution if necessary. High School Diploma or GED.

Special Education Teacher

Company: The Menta Education Group

Location: Chicago, IL

Posted May 21, 2025

IL PEL (Professional Educator's License; out-of-state applicants will need to apply for IL certification) with LBS1 Certification or Other Teacher Certification…

Executive Chef

Company: Aramark

Location: Chicago, IL

Posted May 19, 2025

Interact directly with guests daily. Develop and maintain effective client and guest rapport for mutually beneficial business relationships.

Lead Data Science Product Mgr

Company: Health Care Service Corporation

Location: Chicago, IL

Posted May 18, 2025

Bachelors degree and 5 years of work experience in a mathematical, statistical, computer science, engineering, physics, economics or related quantitative field…

Pet Insurance Sales Associate - Chicago, IL

Company: Fetch Pet Insurance

Location: Chicago, IL

Posted May 20, 2025

Active Property & Casualty (P&C) license or willing to obtain a P&C license at the expense of the Company within 30 days of employment (subject to state…

Sr. Mgr, Software Engineering

Company: Capital One

Location: Chicago, IL

Posted May 19, 2025

Experience leading teams through ambiguity by driving technical design and delivery decisions. Capital One will consider for employment qualified applicants…

Senior Manager, Software Engineer (People Leader)

Company: Capital One

Location: Chicago, IL

Posted May 19, 2025

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

Full Time Janitor (2 years experience required)

Company: TRC Services, Inc.

Location: Skokie, IL

Posted May 21, 2025

*Reporting:* Report any maintenance or repair needs to the Facilities Manager promptly. The Janitor will be responsible for ensuring that locker rooms, offices,…

RETAIL SALES ASSOCIATE

Company: Ashley

Location: Bolingbrook, IL

Posted May 21, 2025

Maintain a welcoming, professional, visible presence at the front desk; engage with guests, ensuring they are always treated in a cordial, respectful manner…

Project Manager- Education Projects

Company: Michael Page

Location: Chicago, IL

Posted May 20, 2025

Establish and maintain working professional relationships with the project design team, company field and office personnel, subcontractors, and vendors.

Mgr Clinical Pharmacy

Company: Rush University Medical Center

Location: Chicago, IL

Posted May 20, 2025

> 6 years practice experience, Pharm.D. with PGY1 and PGY2 training (or equivalent experience), Illinois licensure, and board certification (specialty…

Frequently Asked Questions

What are typical salary ranges by seniority for flexible work arrangement roles?
Junior remote developers earn $70k–$95k, mid‑level professionals earn $95k–$140k, and senior specialists or leads earn $140k–$200k. Remote‑specific allowances can add 5–10% on top of base pay for high‑cost‑of‑living locations.
What skills and certifications are required for flexible work roles?
Core technical skills include Git, Docker, Kubernetes, and proficiency in at least one cloud platform (AWS, Azure, GCP). Remote collaboration skills involve Slack, Zoom, Notion, and Asana. Certifications such as Certified Remote Work Manager, AWS Certified Solutions Architect, Azure Fundamentals, Google Cloud Professional, PMP, or CSM are highly valued.
How widely available are remote work opportunities in this category?
All 2964 positions support remote work, offering full‑time, part‑time, and contract options. Companies provide VPN, zero‑trust security, and remote onboarding tools, enabling employees to start from any location with a reliable internet connection.
What career progression paths exist for professionals in flexible work arrangements?
Typical paths move from Junior Remote Engineer → Senior Remote Engineer → Remote Technical Lead → Remote Engineering Manager or Remote Product Lead. Parallel tracks include Remote UX Lead, Remote Data Lead, or Remote Customer Success Manager, with opportunities to transition into remote operations or CTO roles.
What industry trends are shaping flexible work arrangements?
The remote‑first trend is accelerating, with 60% of tech firms adopting hybrid models by 2025. Adoption of AI‑driven collaboration tools, real‑time code review, and remote cybersecurity protocols is increasing. Companies increasingly offer remote benefits such as home‑office stipends and global health plans, driving higher demand for qualified remote professionals.

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