Find an assistant

Hire a Personal Assistant in Gold Coast, Chicago

Virtual & In-Person Personal Assistant Services

  • 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!

We match you with pre-screened, qualified assistants from our database. You hire your best fit.

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 assistants are designed for that deeper level of ongoing support.

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

Yes! Personal assistants can help research and book travel, support small-scale events like dinner parties or birthday celebrations, and even take on house 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

  • "Gracie has a very keen sense of people's strengths, needs, and personalities that will mix."

    Charles D.

  • “My assistant saves me so much time in my day to day life, and it's a relief knowing I can rely on her."

    Erica W.

  • “The EA we hired continues to be a phenomenal asset to our professional and personal lives. "

    Robert D.

  • “I felt like I never had to lift a finger. From start to finish, working with the Middle was smooth, efficient, and fun."

    Mitchell G.

  • "I was able to find an excellent PA, who has now become essential to streamline and accelerate our work."

    Maria D.

  • "What a brilliant and efficient way to find a personal assistant. A service to find quality candidates looking for hourly work."

    Private Client

  • "The Middle made hiring so much faster and curated such great candidates that the only hard part was making a decision."

    Brian J.

Areas We Serve in California

south bay

Areas We Serve in New York

Areas We Serve in Illinois

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

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

    →

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

    The Benefits of Outsourcing Professional and Personal Tasks

    →

  • Creating a Comprehensive Job Description for Your Personal Assistant

    A Guide To Finding Your Ideal Personal Assistant

    →

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

    Unique Reasons to Hire Personal Assistants in NYC & LA

    →

 FAQs

  • Executive personal assistants bring strong administrative skills that make them well-suited to support individuals with full calendars and demanding personal and professional commitments. Candidates with experience in corporate settings or office support roles often make excellent executive personal assistants. Regardless of their background, we ensure every candidate has solid administrative abilities by having them complete an internal assessment. This includes tasks like creating mock calendar invites, building spreadsheets, and demonstrating attention to detail, organization, and clear communication.

  • Virtual personal assistant services are a great fit for anyone needing help with remote tasks like scheduling meetings, conducting online research, ordering gifts, booking travel, completing registrations, or drafting documents. Even if your assistant works with you entirely remotely, we’ll always match you with someone local to your area and in your time zone. We believe a strong working relationship is key to a successful placement, so we never hide our assistants behind screens—you’ll always have direct access and open communication.

  • The Middle’s personal assistants are comfortable working with clients of all ages. However, our candidates are not licensed or trained medical professionals, so any responsibilities that involve senior caregiving fall outside the scope of their role. That said, they can absolutely assist with home management, organizational projects, tech setup, and other administrative support for older adults and professionals.

  • The Middle specializes in part-time, ongoing placements and typically does not place personal assistants for short-term or seasonal projects. That said, we may have candidates open to this type of work. Just let us know your needs in the Client Questionnaire, and we’ll match you with candidates who fit your needs.

  • We typically share up to 5 curated candidate matches at a time, carefully selected based on your needs. However, if you’d like a larger selection, we’ll share as many as we have who are a fit for your needs. You're welcome to interview as many candidates as you'd like until you feel confident in your hire.

  • The Middle does not issue contracts guaranteeing a set length of employment. While these roles are intended to be long-term, Illinois is an at-will employment state, which means either the employee or employer can end the working relationship at any time.

  • Evenings and weekends are outside of typical working hours for personal assistants. If availability during these times is required or preferred, please indicate so in our Client Questionnaire and we’ll do our best to match you with candidates who are open to working evenings and/or weekends.

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.