At The Middle, hiring a personal assistant in Streeterville tailored to your lifestyle is easy. Whether you’re busy commuting to nearby hospitals and offices, managing your condo along Michigan Avenue, or trying to stay ahead of errands and scheduling appointments, we’ll match you with a qualified part-time assistant who keeps your days clear and organized.
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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!
How Personal Assistant Services Differ Between Virtual and In-Person Options in Streeterville
The Middle specializes in connecting you with local personal assistants who can support you either in person or virtually, depending on your needs. The key difference is how the work gets done—but no matter the setup, your assistant will always be based in your city, ready to offer flexible, reliable support. Even for virtual roles, The Middle prioritizes local matches so that you have the option for face-to-face collaboration if and when needed.
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Ideal when you need hands-on help like running errands, managing home organization projects, or handling other tasks that require a physical presence.
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Focused on remote support, such as scheduling, inbox management, online research, or document preparation.
What types of clients typically hire a personal assistant in downtown Chicago?
Chicago clients who work with The Middle are typically busy professionals who need reliable, part-time support to help keep their lives running smoothly. This includes entrepreneurs, consultants, attorneys, creatives, small business owners, and working parents—anyone juggling a full workload and limited hours in the day. Many are not quite ready for a full-time hire but still need dedicated, flexible help with personal tasks, logistics, and admin support. Whether you're managing a growing business, a hectic household, or both, The Middle matches you with assistants who can seamlessly step in and support your day-to-day life.
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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![A close-up of a man with a short haircut, goatee, and mustache, wearing a white shirt and black blazer, standing in front of a backdrop with the text 'TV Land' on it.]()
"Gracie has a very keen sense of people's strengths, needs, and personalities that will mix."
Charles D.
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![A woman smiling with her hand on her face, wearing a light blue blazer, against a light 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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“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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![Young woman with shoulder-length dark hair, smiling, wearing a navy blazer and black blouse with ruffled collar, standing in front of a beige 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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While personal assistants from The Middle are not office assistants and are not trained or licensed to support in a clinical capacity, they can help you stay focused on your work by making sure everything outside of your professional responsibilities is running smoothly. By taking day-to-day personal responsibilities off your plate—like running errands, coordinating schedules, handling travel logistics, or managing household tasks—a personal assistant can free up your time and mental space so you can concentrate on your clinical duties.
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While personal assistants from The Middle are not office assistants and don’t provide direct support with clinical or legal work, they can offer valuable help behind the scenes. Our assistants can take on a wide range of administrative and personal responsibilities. This might include managing calendars, coordinating travel, handling errands, organizing documents, or overseeing household logistics. By taking care of the details, your assistant helps free up your time so you can stay focused on the higher-level demands of your work.
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Absolutely! You can interview as many candidate matches as we have for you. Interviewing is free of charge and there is no commitment until you are ready to hire.
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Absolutely! The Middle specializes in matching individuals with busy lives and demanding schedules with part-time, local personal assistants. Our assistants can manage all of your routine tasks, day-to-day to dos, and ad hoc projects that keep your life running smoothly.
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While personal assistants from The Middle are not teaching assistants and don’t provide academic or classroom support, they can offer support to faculty members balancing teaching, research, and personal responsibilities. Our assistants can help with a wide range of administrative and day-to-day tasks like scheduling, travel planning, organizing files, running errands, or managing personal logistics.
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The Middle has set plans or required minimums. While candidates will expect around the number of hours you identify when filling out our Client Questionnaire, positions can be flexible to meet your weekly needs.
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Personal assistants can help you plan and coordinate travel, and may also assist with smaller, general aspects of conference preparation such as organizing materials you share with them, researching venues or accommodations, and refining your presentation deck. However, large-scale event planning typically falls outside the scope of a personal assistant’s role.
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Our candidates are proactive and strategic. If running errands within Streeterville is clogged with summer tourist traffic, your assistant can route their shopping and pickups to adjacent neighborhoods to maximize their efficiency.
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Our candidates are adaptable to shifting schedules. Whether you need them to run errands while you are on a long shift or require remote help during your off hours, we can match you with someone who complements your demanding medical schedule.
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Our pricing model reflects part-time support. We charge a flat $750 placement fee upon hiring. After that, your hourly personal assistant will track their time and bill you directly, typically at a rate of $25 to $40 per hour. Because there are no minimums, you only pay for the exact hours worked.
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Our talent pool is diverse. If you require a personal administrative assistant to help with drafting documents, online research, detailed spreadsheet management, or complex scheduling, we can provide candidates who possess strong executive skill sets for either in-person or remote work.
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If you need a concierge personal assistant who excels at securing exclusive dining reservations, planning private dinners, or organizing travel itineraries, we will only match you with candidates who have a proven track record in lifestyle management.
Hiring a Personal AssistantWhat Busy Professionals in Streeterville Should Look For When Hiring a Personal Assistant
If you're hiring a personal assistant, it’s important to look for someone who is reliable, proactive, and adaptable and can handle a range of tasks that support your life both personally and professionally. That’s where we come in! Our screened qualified candidates can help manage appointments, run errands across the city, coordinate family logistics, or keep your inbox in order. Our assistants are resourceful, organized, and comfortable navigating a fast-paced urban environment. You’ll also want someone with strong communication skills and a good sense of discretion—someone you can trust as an extension of yourself. Our interview process allows you to meet candidates face to face before making a hire so you can gauge your interpersonal connection.
Next Steps to Start The Personal Assistant Hiring Process
Getting started is easy! Just fill out our Client Questionnaire, and we’ll send personalized candidate matches straight to your inbox. From there, we’ll coordinate interviews at your convenience so you can meet each candidate, learn more about their experience, and choose the right fit for your needs.