Flexible Work Arrangements Jobs in Chicago, IL

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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.

Data Scientist

Company: PayPal

Location: Chicago, IL

Posted Sep 03, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Part-time Dishwasher/Special Events Maintenance Support

Company: Little Black Pearl Art & Design Academy

Location: Chicago, IL

Posted Sep 03, 2025

REQUIREMENTS:* High School Diploma; ability to perform duties with little oversight; responsible communications. PAY PERIOD:* 10th and 25th of each month.

Retail Sales Associate (Electronics Repair)

Company: Asurion

Location: La Grange, IL

Posted Sep 02, 2025

Provide technical expertise, troubleshoot, and repair customer electronic devices. Through interactions with customers, our experts demonstrate integrity in…

CDL A Transportation Driver - Home Daily

Company: Dayton Freight

Location: Des Plaines, IL

Posted Sep 03, 2025

At least 18 months of commercial driving experience. Perform pre and post trip inspections on tractor/trailer. Maintain cleanliness of company vehicle.

Medical Contact Center Agent (Bilingual English/Spanish)

Company: The Chicago Lighthouse

Location: Chicago, IL

Posted Sep 03, 2025

STATEMENT OF PURPOSE: The Medical Contact Center Agent will be responsible for outbound and inbound calls, voicemails, and emails to/from insurance plan members…

Registered Nurse - Cantonese Bilingual

Company: Oak Street Health

Location: Chicago, IL

Posted Sep 03, 2025

Active Registered Nurse (RN) Licensure in good standing with the applicable state. Qualified applicants with arrest or conviction records will be considered for…

Club Housekeeper | Union Padel Club

Company: Lakeshore Sport & Fitness

Location: Chicago, IL

Posted Sep 03, 2025

As a Club Housekeeper, you’ll be responsible for making sure our courts, locker rooms, lounges, and other areas are always clean, safe, and welcoming for…

Lead Software Engineer (Java & AWS)

Company: Capital One

Location: Chicago, IL

Posted Sep 03, 2025

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

Special Agent: Education/Teaching Expertise

Company: Federal Bureau of Investigation

Location: Chicago, IL

Posted Sep 03, 2025

Candidates must have a bachelor’s degree or higher (preferably in education or a related field) from a U.S. accredited college or university.

Executive Kitchen Manager

Company: Cooper's Hawk Winery & Restaurants

Location: Oak Park, IL

Posted Sep 03, 2025

Preferred certifications include ServSafe and state/local licensing requirements. Ensure strong collaboration between kitchen and front-of-house operations.

Staff Software Engineer

Company: Grainger

Location: Chicago, IL

Posted Sep 03, 2025

Proven experience collaborating across teams to develop and implement software engineering best practices. Providing the right product at the right price is…

Retail Sales Associate- Water Tower (Part Time)

Company: Eileen Fisher

Location: Chicago, IL

Posted Sep 03, 2025

Employee and Friends & Family discount. Ability to climb short/tall ladders, twist, bend, and stoop to retrieve items from floor, shelves, and hooks.

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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