At The Middle, hiring a personal assistant in the West Loop means you have backup for life between personal plans and work commitments. Whether you’re juggling client meetings, managing a family schedule, or trying to stay on top of errands, overflowing inboxes, and home management, we’ll match you with a qualified part-time assistant who keeps your days running smoothly.
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Save Time
Delegate all the little time sucks and reclaim your life.
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Boost Productivity
We’ll do the admin so you can focus on higher-level projects.
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Reduce Stress
Find The Middle ground in work/life balance.
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No Set Plans
Personalized support tailored to your needs.
How It Works
Match with candidatesSay goodbye to combing through applications! Tell us about what you looking for, and receive your matches.
interview your favoritesAvoid the hassle of coordinating. Simply provide your availability and we’ll set up a video interview.
hire Assistant + get startedPositions are part-time, but ongoing. Pay your assistant their wages directly and enjoy your newfound time!
The best way to hire a personal assistant in Chicago’s West Loop
Looking to hire a personal assistant in Chicago? We’ve got you covered.
At The Middle, we specialize in part-time, long-term placements—connecting busy people with reliable, local personal assistants in Chicago.
We take the legwork off your plate by screening applicants, doing initial interviews, and giving skills assessments. That way, you get a curated list of qualified candidates to choose from—no sorting through endless resumes required!
Find a personal assistant to help with your business calendar and personal life logistics (and more!)
Personal assistants with The Middle are skilled at managing both the professional and personal sides of your life. Whether it’s coordinating meetings, keeping your calendar organized, or booking travel for a work trip, our assistants have your business needs covered. But their support doesn’t stop there.
They can also handle personal life logistics like scheduling doctor’s appointments, overseeing home repairs, picking up dry cleaning, or making sure your pantry is stocked.
Our candidates are used to supporting busy professionals and know how to move seamlessly between business and personal tasks. Think of them as an extra set of hands helping to keep every part of your life running smoothly.
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
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"Gracie has a very keen sense of people's strengths, needs, and personalities that will mix."
Charles D.
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“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.
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“The EA we hired continues to be a phenomenal asset to our professional and personal lives. "
Robert D.
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“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.
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![A woman with shoulder-length black hair, wearing a dark blazer over a black blouse with ruffled edges, smiling in front of a light-colored wall with abstract cut-out shapes.]()
"I was able to find an excellent PA, who has now become essential to streamline and accelerate our work."
Maria D.
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"What a brilliant and efficient way to find a personal assistant. A service to find quality candidates looking for hourly work."
Private Client
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"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 bayAreas We Serve in New York
Areas We Serve in Illinois
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The Difference Between Part-Time and Full-Time Personal Assistants
Why a Part-Time Personal Assistant Might Be the Perfect Fit for Your Needs
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Maximize Your Day: How a Personal Assistant Can Streamline Your Schedule
The Benefits of Outsourcing Professional and Personal Tasks
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Creating a Comprehensive Job Description for Your Personal Assistant
A Guide To Finding Your Ideal Personal Assistant
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Why New York City & Los Angeles Are Perfect for Personal Assistants
Unique Reasons to Hire Personal Assistants in NYC & LA
FAQs
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Part of our process is matching you with candidates who have relevant experience. If you’re looking for an executive personal assistant, please share your needs by submitting a Client Questionnaire. We’ll review your responses and match you with candidates who have relevant experience.
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We’ve found that the tasks busy professionals most often need help with are running errands and scheduling appointments. They’re simple enough, but they take up valuable time and mental space. Delegating these kinds of to-dos to a personal assistant frees you up to focus fully on your work, knowing that the small (but important) things at home are being handled.
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You can hire a local personal assistant in Chicago’s West Loop through The Middle. Even if most of the support you need is remote, our candidates are based in your area so when something pops up that needs to be handled in person, you’ve got someone nearby who can step in. We make it easy to build a real, working relationship with your assistant—not just another name behind a screen.
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Personal assistants with The Middle can assist with researching vendors, organizing digital information, and creating systems. Share the relevant experience you’re looking for in our Client Questionnaire and we will match you with candidates who fit your needs!
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The Middle places part-time positions. Personal assistant candidates are typically looking for up to 25 hours, but can offer support for as little as 5 hours per week. The work is expected to take place during the work week (Monday-Friday, 9am-6pm), and our assistants are not expected to available at your disposal 24/7.
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A virtual personal assistant from The Middle can be a game-changer for consultants and founders juggling multiple responsibilities. Here's how they can support your work:
Streamline Administrative Tasks
Free up your time by delegating routine tasks such as managing your calendar, scheduling meetings, handling email correspondence, and organizing documents. This allows you to focus on strategic decision-making and client engagement.
Enhance Communication
Your assistant can manage communications with clients, vendors, and team members, ensuring timely responses and helping maintain professional relationships.
Support Project Management
Assistants can help track project timelines, set reminders, and ensure that deliverables are met, keeping your projects on schedule.
Manage Finances
They can assist with invoicing, expense tracking, and basic bookkeeping, providing you with up-to-date financial information to make informed decisions.
Conduct Research
Whether it's market research, competitor analysis, or sourcing tools and resources, your assistant can gather and summarize information to support your business strategies.
Customized Support
The Middle matches you with assistants who have experience relevant to your industry and specific needs.
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Our process is designed to be straightforward and simple. Start by filling out our Client Questionnaire and we will share candidate matches based on your needs.
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Whether you need someone to run to a local electronics store, manage the return of office equipment, or help physically organize your home workspace, our candidates are hands on and ready to help optimize your environment for maximum productivity.
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It is very common for our entrepreneurial clients to need a business personal assistant. Your hire can transition from doing data entry and inbox management for your startup in the morning to picking up your dry cleaning and booking restaurant reservations in the afternoon.
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If you want to take shopping completely off your plate, your personal assistant can easily act as your personal shopping assistant. From handling weekly grocery runs and farmers market trips to picking up specific clothing items, they can make sure your home is fully stocked with exactly what you need.
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The Middle specializes exclusively in part-time, ongoing placements, with flexibility for both our clients and our talent. While we do not place full-time corporate roles or full-time medical private aide positions, our part-time assistants can dramatically reduce your weekly workload and help you reclaim your time.
Hiring a Personal AssistantHow a Virtual Assistant Compares to an In-Person Personal Assistant
When considering whether to hire a virtual or in-person personal assistant through The Middle, it's important to understand the difference between the two roles.
Virtual Personal Assistants
Virtual assistants primarily handle tasks that can be completed remotely, such as:
Administrative Support: Managing calendars, scheduling meetings, and handling email correspondence.
Calendar Management: Scheduling and coordinating meetings, events, and travel.
Research and Coordination: Conducting online research, booking travel, and coordinating logistics.
In-Person Personal Assistants
In-person assistants can perform all the functions of a virtual assistant, with the added capability to handle tasks that require physical presence, such as:
Errand Running: Picking up groceries, dry cleaning, or other items.
Home Organization: Assisting with organizing spaces, overseeing home projects, or managing household staff.
Onsite Support: Meeting with household service providers, helping set up a small event, or other ad-hoc tasks that take place in your home.
At The Middle, both types of assistants are based in your local area, ensuring familiarity with your city and alignment with your time zone.
Qualities To Look For When Hiring An Executive Personal Assistant in West Loop
When hiring an executive personal assistant in Chicago’s West Loop through The Middle, it's essential to consider both hard and soft skills to ensure a successful partnership. Here's what to look for:
Key Skills and Experience
Organizational Abilities: Seek assistants who can manage calendars, coordinate appointments, and keep tasks on track.
Time Management: Candidates should be adept at prioritizing tasks and managing their schedules efficiently.
Communication Skills: An executive assistant should have excellent verbal and written communication skills.
Tech Proficiency: Familiarity with tools like Google Workspace, Microsoft Office, and task management apps is beneficial.
Project Management: Experience in overseeing projects and ensuring deadlines are met is valuable.
Interpersonal Qualities
Reliability: Consistency and dependability are crucial for ongoing support.
Flexibility: Since part-time roles can vary week to week, adaptability is key.
Discretion: Handling personal and sensitive information requires a high level of trustworthiness.
Proactivity: Assistants who take initiative can add significant value by identifying and addressing needs before they arise.
The Middle pre-screens candidates to ensure they possess these qualities and match your specific requirements. During the interview process, it's beneficial to discuss your expectations and assess how well the candidate's experience and personality align with your needs.