Locations | CHICAGOHire a Personal Assistant in Chicago
Part-Time Personal Assistant Services in Chicago
The Middle’s Chicago assistant services give busy professionals and families an accessible way to manage life’s to-do list, from errands and scheduling to inbox and calendar support. We’ll match you with a qualified personal assistant in Chicago who fits your needs and work style, so you can stay focused on whatever really requires your attention.
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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!
We match you with pre-screened, qualified assistants from our database. You hire your best fit.
Typical Responsibilities of a Personal Assistant
Personal assistant responsibilities range from returning packages to scheduling appointments to booking travel, and everything in between.
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Running errands (e.g., grocery shopping, dry cleaning)
Returning packages and handling online purchases
Stocking household supplies and groceries
Setting up devices and managing household technology
Home organization and decluttering projects
Coordinating home maintenance and repairs
Managing household staff (e.g., housekeepers, nannies)
Assisting with moves or relocations
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Keeping track of life logistics so you don’t have to
Handling the lingering “I’ll get to it later” tasks
Streamlining weekly routines, reminders, and planning
Finding solutions for everyday friction points (like meal prep, storage, or scheduling)
Helping you follow through on personal goals or home projects
Acting as a go-to support system to free up headspace
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Scheduling appointments, meetings, travel, and events
Managing calendars and coordinating schedules
Handling email correspondence and achieving inbox zero
Preparing documents and data entry
Organizing digital files and maintaining records
Conducting online research (e.g., vendors, service providers)
Paying bills and managing subscriptions
What To Know Before Hiring a Personal Assistant in Chicago, IL
Before hiring a personal assistant through The Middle, you should know a few basics:
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Personal assistants can handle a wide range of support tasks, from business to personal support, but some areas of support are not within the scope of work of a personal assistant. These include: childcare or senior caregiving, laundry/cleaning, social media management, and cooking. Some candidates have experience or are willing to support in these areas, but coverage should not be expected.
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Our part-time personal assistants are not on-call or expected to be at your disposal 24/7. You are welcome to set a schedule with your PA, or work asynchronously. If you work asynchronously, expect work to be done in a timely manner but understand it won’t always be completed as soon as the task is received (that would make your PA “on-call”).
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Mileage (or public transportation fare) should be reimbursed for driving done on the job (errands, etc.), but is not a required reimbursement for commutes.
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Understand there will always be a learning curve when two individuals start working together! Don’t expect your PA to read your mind on Day 1. You’ll need to put in a little legwork/training to get your PA up and running, but then they should be able to work independently according to your preferences.
Who Hires an Assistant with The Middle Personal Assistant Agency in Chicago?
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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![A man with short dark hair, a trimmed beard, wearing a white patterned shirt and black blazer, smiling at the camera with a dark backdrop and partially visible TV Land logo.]()
"Gracie has a very keen sense of people's strengths, needs, and personalities that will mix."
Charles D.
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![A young woman with long, wavy brown hair, smiling and touching her face with her left hand, wearing a light blue blazer against a blue background.]()
“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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![Purple letters 'RD' on a light blue background.]()
“The EA we hired continues to be a phenomenal asset to our professional and personal lives. "
Robert D.
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![Light blue background with large purple letters 'MG' centered.]()
“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 dark hair, wearing a dark blazer and black ruffled blouse, smiling in front of a beige wall with abstract cutouts.]()
"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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![Light blue background with large purple letters 'SC' in the center.]()
"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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![Light blue background with large purple letters 'BJ' in the center.]()
"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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An executive personal assistant is an assistant who supports an individual with both their personal and business-related needs. Often these roles are for entrepreneurs and business owners, but could also include support for a busy individual who needs to offload higher-level responsibilities like coordinating small events, managing and coordinating philanthropic and volunteer activities, and support preparing financial documents.
A household assistant solely supports home-related tasks, such as managing housekeepers, researching kid’s summer camps and schools, and stocking groceries. A household assistant might support multiple members of the household, not just a principal individual.
The Middle places personal assistants, executive personal assistants and household assistants. Household assistants with The Middle do not manage housekeeping duties such as laundry and cleaning. Let us know your needs in your Client Questionnaire and we’ll help you find the perfect personal assistant in Chicago, IL.
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A personal assistant in Chicago is happy to offer virtual assistant services too. Simply let us know in our Client Questionnaire if you are looking for in-person support or remote support, and we’ll match you with candidates accordingly. Regardless of where you are based in Chicago, our candidates are always local (so they’ll always be in your time zone).
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To prepare for working with an assistant, we recommend keeping a list of all of the tasks that could be handled by someone else for up to a month. Take a look at this list and determine how much of it requires your personal assistant to be in-person (home tasks like grocery shopping and home organization) and how much can be done remotely (like scheduling doctors’ appointments and researching/booking travel). If all of your tasks can be done remotely, you need a virtual personal assistant! If you have tasks that require in-person support, then you’ll want someone who can come to your home as needed. Candidates at The Middle are able to provide both, and are always based in your area.
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The typical hourly rate for a personal assistant in Chicago, IL is $25-$35/hr. Some candidates may command a higher rate depending on their experience, and most candidates with The Middle have a $25/hr minimum.
The Middle’s personal assistant services in Chicago incur a one-time Placement Fee of $750, due upon hire. That’s it!
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The Middle focuses on part-time personal assistant jobs in Chicago. We do not place full-time personal assistant positions. Our candidates offer personal assistant services in Chicago for no more than 25 hours per week.
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Yes! The Middle has no minimums or set plans. We match you with qualified, local personal assistants ready to help you for as little as a few hours a week.
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The Middle is a personal assistant agency that does not service just one industry. We are here to support any busy person. Some of our clients include consultants, entrepreneurs, small business owners, medical professionals, and marketing executives.
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Our process is designed to be streamlined and quick. All candidates are pre-screened, allowing you to focus on your specific needs in interviews. We’ll present qualified candidates within two weeks (and often in under a week) and schedule interviews at your convenience. Once you’ve made your choice, we’ll connect you directly with your selected assistant so you can get started right away.
Hiring a Personal AssistantReasons to Hire a Personal Assistant in Chicago
Hiring a personal assistant can help streamline your daily life. Say goodbye to that nagging to do list and say hello to a clear mind and freed up time! Our personal assistants can handle personal errands, life admin, and even business support so you can focus on family time, your personal life, and higher level projects. Ultimately, hiring a personal assistant relieves stress in your life knowing you have a trusted partner catching everything that can fall through the cracks.
Qualifications to Look for in a Personal Assistant
When hiring a personal assistant, it's important to find someone with the right experience and skills for your specific needs. We’ll help match you with candidates who meet those requirements. While interviews are essential for understanding communication styles and clarifying role expectations, you can trust that every candidate we present is already fully qualified. We prioritize key skills such as clear communication, strong organizational habits, time management, and effective problem solving.