locations | Chicago | River north

Personal Assistants for Hire in River North, Chicago

River North Chicago - In-Person and Virtual Personal Assistant Services

Hiring a personal assistant in River North with The Middle gives you local, reliable support to keep up with errands, reservations, and household management. We match you with a qualified part-time assistant who keeps your schedule and home life running smoothly.

downward facing arrow
  • Save Time

    Delegate all the little time sucks and reclaim your life.

  • Boost Productivity

    We’ll do the admin so you can focus on higher-level projects.

  • Reduce Stress

    Find The Middle ground in work/life balance.

  • No Set Plans

    Personalized support tailored to your needs.

How It Works

Match with candidates

Say goodbye to combing through applications! Tell us about what you looking for, and receive your matches.

interview your favorites

Avoid the hassle of coordinating. Simply provide your availability and we’ll set up a video interview.

hire Assistant + get started

Positions are part-time, but ongoing. Pay your assistant their wages directly and enjoy your newfound time!

River North Chicago Personal Assistant Looking at Letter and Using Laptop

Benefits of Hiring a Personal Assistant in River North

Hiring a personal assistant who lives nearby means getting the kind of hands-on support that virtual assistants simply can’t provide.

  • Hands-On Help: Local assistants can take care of things that require someone physically there—like running errands, organizing your home, or meeting service providers.

  • Personal Connection: Working together in person makes it easier to build a strong, trusting relationship. Communication flows more naturally when you're face-to-face.

  • Reliable On-Site Support: Whether it's letting in a repair technician or helping with a move, it’s incredibly helpful to have someone you trust right there when you can’t be.

A River North Chicago Personal Assistant Holding a Laptop and Talking with Employer

The Difference Between a Personal Assistant and an Executive Assistant

A personal assistant typically helps with household and personal to-dos, while an executive assistant usually focuses on business needs in an office setting. At The Middle, our candidates are comfortable handling both types of tasks. They support busy individuals with a blend of personal and professional tasks, and often split their time between working in your home and working remotely, rather than commuting to an office every day.

  • Personal support might include things like running errands, organizing your home, or managing appointments.

  • Business support could look like scheduling meetings, doing online research, or keeping databases up to date.

Who Hires an Assistant with The Middle?

Small Business Owners

Consultants

Project Managers

Entrepreneurs

Philanthropists

Marketing Experts

Branding Creatives

Writers

Investors

Tech Founders & Engineers

Film, TV & Media Executives

Interior Designers

Artists

Real Estate Professionals

Lawyers

Satisfied Clients

Areas We Serve in California

south bay

Areas We Serve in New York

Areas We Serve in Illinois

  • A young woman smiling, holding a coffee cup in one hand and a laptop in the other, outdoors in an urban area with colorful buildings in the background, wearing a beige coat and a wide-brimmed hat.

    The Difference Between Part-Time and Full-Time Personal Assistants

    Why a Part-Time Personal Assistant Might Be the Perfect Fit for Your Needs

  • A young man with dark, curly hair and a beard, wearing a light blue shirt, smiling and holding papers, seated at a desk across from a woman in a green top. The background includes shelves with plants and storage boxes, and the desk has a laptop, a coffee cup, and a small potted plant.

    Maximize Your Day: How a Personal Assistant Can Streamline Your Schedule

    The Benefits of Outsourcing Professional and Personal Tasks

  • Person wearing a green knitted sweater writing in a notebook with a silver pen, with a laptop open in front of them.

    Creating a Comprehensive Job Description for Your Personal Assistant

    A Guide To Finding Your Ideal Personal Assistant

  • A young woman with curly hair stands on a subway platform, smiling and looking up. She is wearing a denim jacket, a yellow top, earrings, and a necklace, with a black backpack slung over her shoulder.

    Why New York City & Los Angeles Are Perfect for Personal Assistants

    Unique Reasons to Hire Personal Assistants in NYC & LA

 FAQs

Hiring a Personal Assistant

The Difference Between Virtual Assistant Services and In-Person Support In River North

If you're juggling life and business and want someone who can be there—not just online—an in-person assistant from The Middle is for you.

Virtual Assistant Services

  • Remote support only: Virtual assistants work from afar, handling digital tasks like email management, social media, research, and scheduling.

  • Cost-effective and flexible: Rates tend to be lower since there’s no need for physical office space or equipment—and remote assistants can be sourced globally.

  • Ideal for digital or administrative needs: Best for tasks that don’t require anyone being physically present.

In-Person Support

  • Physical proximity: Our assistants work in and around your home—not in a corporate office—so they’re available for errands, household coordination, and other in-person tasks.

  • Blended role = personal + business: Unlike executive assistants who operate in an office environment, our personal assistants support both your day-to-day home life and front-office needs.

  • Tasks that require presence: They can stock groceries, organize your space, welcome vendors, run errands, and handle both business and personal admin smoothly

Good Questions To Ask When Interview Interviewing Prospective Personal Assistants

1. What interests you about this position?

  • Helps you understand their motivation and how well their values and interests align with your needs.

2. What prior experience have you had that transfers to this position?

  • Encourages them to highlight relevant skills—like organization, scheduling, household management, or creative project support.

3. I need [describe your needs]. Why do you feel uniquely equipped to fill those needs?

  • Tests how well they listen and tailor their responses to your specific requirements.

4. What is your current availability? Let’s discuss what working together would look like week‑to‑week.

  • Crucial for clarifying scheduling expectations and any flexibility required.

5. How would you keep us organized and on track?

  • Shows their approach to systems, workflows, and proactive planning.

6. What questions do you have for me?

  • Reveals their curiosity, engagement level, and what matters to them in a role.

To learn more about our recommended interview best practices, review our Interview Tips.