Locations | CHICAGO | GOLD COAST

Hire a Personal Assistant in Gold Coast, Chicago

Gold Coast Virtual & In-Person Personal Assistant Services

At The Middle, hiring a personal assistant in the Gold Coast gives you a trusted partner to handle the tasks that keep piling up. We connect busy professionals and residents with carefully screened part-time assistants for errands, scheduling, admin support, and everyday organization.

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  • 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!

Gold Coast Chicago Personal Assistant Cleaning Kitchen and Doing Dishes

Difference Between a Concierge and a Personal Assistant in the Gold Coast

Traditionally, a concierge handles on-the-ground, one‑off errands or services like restaurant reservations, travel bookings, gift purchases, package delivery, or personal errands. It’s often transaction-based, available as needed rather than through an ongoing relationship.

Personal assistants from The Middle offer a deeper, ongoing support system, handling both personal and professional administrative tasks. This includes managing calendars, booking travel, drafting documents, overseeing home organization, liaising with service providers, and more.  If you want reliable, multifaceted assistance over time, The Middle’s personal assistant positions are designed for ongoing support.

Part Time Personal Assistant in Gold Coast Chicago Doing Laundry

Do personal assistant services include help with travel, events, or household management?

Yes! Personal assistants can research and book travel, support small-scale events like dinner parties or birthday celebrations, and even take on household management tasks. Their event support might include ordering supplies, coordinating with caterers, or helping with setup. As a house manager, they can stock groceries and supplies, manage organizational projects, and communicate with nannies, housekeepers, or other service providers.

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

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 FAQs

Hiring a Personal Assistant

Process To Hire A Personal Assistant For Your Household in Chicago’s Gold Coast

The Middle makes it easy for you to hire a local, part-time personal assistant to support you and help manage your Chicago household. Start by filling out our Client Questionnaire and we’ll match you with the right candidates who fit your needs. We’ll match you with candidates who have relevant experience, organizational skills, and the ability to streamline busy schedules with multiple moving parts. Simply select who you’d like to interview from our curated list, and we’ll coordinate and schedule an interview schedule at your convenience. Then, hire your favorite and get started!

Good Questions To Ask When Interviewing a Personal Assistant

These questions are designed to help you assess not just qualifications, but also working style, flexibility, and long-term fit:

  1. What interests you about this position?
    Helps gauge their motivation and whether they’re genuinely excited about the role.

  2. Can you tell me about past experience that relates to this position?
    Understand how their background translates to the kind of support you need.

  3. I need help with ___ (e.g., calendar management, errands, travel planning). Why do you feel confident handling that?
    Tailor this to your priorities and see how they align with the assistant’s strengths.

  4. What is your current availability, and how do you typically like to structure your week?
    Clarifies scheduling expectations early on.

  5. How would you keep me (or our household) organized and on track?
    Insight into their approach to structure, systems, and proactivity.

  6. What types of tasks are you most comfortable with?
    A good way to find out what they enjoy or excel at—and what they might prefer to avoid.

  7. How do you prioritize when multiple deadlines or requests come in at once?
    Tests time management and problem-solving skills.

  8. Do you have any questions for me?
    Look for thoughtful questions that show genuine interest and engagement.

Review our Interview Tips for more recommendations on best practices for interviewing.