Hire a Personal Assistant in 24h
Premium Personal Assistant recruitment in Chicago, USA. Vetted candidates delivered fast, no upfront fees.




Why Elite Employers Choose Us
For over 20 years, Lighthouse Careers has been the trusted partner for discerning clients seeking exceptional Personal Assistant professionals. Our rigorous vetting process ensures only the highest caliber candidates.
Rigorous 7-Step Vetting
Background checks, reference verification, and skill assessments
24-Hour Candidate Delivery
Receive your first shortlist within two business days
Success-Fee Model
No upfront costs - you only pay when you hire
Replacement Guarantee
Free replacement if placement doesn't work out
How It Works
Our streamlined process gets you qualified candidates fast.
Share Your Requirements
Tell us about your household or yacht, the role you need filled, and your specific requirements.
Receive Matched Candidates
We search our network and present a shortlist of pre-vetted candidates tailored to your needs.
Interview & Hire
Meet your candidates, conduct interviews, and make your selection with our full support.
Trusted by Industry Leaders
Hear from captains, estate managers, and professionals who have found exceptional talent through Lighthouse Careers.
"I wanted to say a few words of thanks for your all your time and efforts over the past few years. You and your team has always been a massive help in trying to help find us the right candidate for the right job in this ever expanding and delicate industry."

"I've had the pleasure of knowing Milica, and using her recruitment services for many years. Her attention to what I'm looking for in a crew member, fast response and flexibility and understanding of feedback has always impressed me."

"Milica is always my first call when looking for new crew. She helped me get my first command 3 years ago and ever since has supplied me with great candidates for all positions onboard."

"Due to her industry knowledge, great candidates she has provided over the years and great sense of urgency, I decided to appoint Milica's agency to represent our fleet of yachts. It has certainly proved to be a great partnership."

"I have known Milica for over a decade. In that time I have come to value her judgement and advice on Crew Recruitment. She has placed a number of candidates on my commands and she has also helped me secure my dream job!"

"Throughout my 11 years in yachting, I have found Milica to be my go-to agent for jobs. Not only because she has a great reputation in the industry and great boats in her books but also for her care, kindness and professionalism."

About Personal Assistant Positions
When ultra-high-net-worth families and executives in Chicago seek to hire a Personal Assistant, they require more than basic administrative support—they need a sophisticated professional who can seamlessly integrate into their luxury lifestyle while maintaining the highest standards of discretion and service excellence. A Personal Assistant in Chicago, USA working in private service becomes an indispensable extension of their principal, orchestrating complex schedules, managing confidential affairs, and ensuring every detail of their employer's personal and professional life runs flawlessly.
Core Responsibilities of Elite Personal Assistants
Exceptional Personal Assistants in luxury households manage far more complex duties than traditional corporate assistants. They serve as the central coordination point for all aspects of their principal's life, requiring exceptional organizational skills and unwavering attention to detail.
- Complex Travel Coordination: Arranging private jet schedules, luxury accommodations, and detailed itineraries for global travel
- Household Management Support: Liaising with House Managers, Private Chefs, and other household staff to ensure seamless operations
- Personal Project Management: Overseeing renovations, art acquisitions, charitable events, and family celebrations
- Executive Support: Managing correspondence, scheduling high-level meetings, and coordinating with business offices
- Lifestyle Management: Securing reservations at exclusive venues, managing wardrobe needs, and coordinating personal services
- Confidential Affairs: Handling sensitive information with absolute discretion and maintaining strict confidentiality protocols
Essential Qualifications and Chicago Market Insights
Chicago's vibrant business district and luxury residential areas, from Gold Coast mansions to Lincoln Park estates, demand Personal Assistants with exceptional credentials and local market knowledge. Employers should seek candidates with relevant certifications such as the Certified Administrative Professional (CAP) designation and specialized training in luxury service protocols.
Key Qualifications to Prioritize:
- Bachelor's degree preferred, with 5+ years in high-net-worth family service or executive assistance
- Proven experience managing complex international travel and luxury lifestyle coordination
- Advanced proficiency in technology, including security-conscious communication platforms
- Multilingual capabilities advantageous for Chicago's international clientele
- Impeccable references from previous luxury household positions
A professional Personal Assistant brings invaluable peace of mind to busy executives and families, allowing them to focus on their priorities while ensuring every personal detail is expertly managed with the sophistication and discretion that defines luxury private service.
Personal Assistant Market in Chicago, USA
Hiring a Personal Assistant in Chicago, USA: Local Market Overview
Chicago's thriving luxury market creates exceptional demand for elite household staff, particularly in prestigious neighborhoods like Gold Coast, Lincoln Park, and Lake Forest. Ultra-high-net-worth families in the Windy City seek highly skilled professionals who can navigate the city's dynamic business environment while managing complex personal affairs. When you hire Personal Assistant Chicago, USA, you're accessing a talent pool that understands both corporate sophistication and refined domestic service standards.
Compensation and Market Dynamics
A Personal Assistant in Chicago, USA commanding positions within UHNW households typically earn between $85,000-$150,000 annually, with exceptional candidates reaching $200,000+ for comprehensive roles requiring specialized skills. The competitive market reflects Chicago's position as a major financial center, where principals often require assistants familiar with:
- Corporate board coordination and high-level meeting management
- Private aviation scheduling through Chicago's executive airports
- Luxury real estate management across multiple properties
- Cultural event planning leveraging Chicago's renowned arts scene
Local Considerations
Chicago's harsh winters create unique logistical challenges, making weather-adaptable assistants particularly valuable. The city's international business connections often require candidates comfortable with global time zones and cultural protocols. Many families maintain residences in nearby Hinsdale, Winnetka, or Lake Geneva, requiring assistants skilled in multi-property coordination. Illinois employment law knowledge and discretion regarding financial services industry connections are essential qualifications for top-tier positions.
Frequently Asked Questions
Common questions about hiring a Personal Assistant in Chicago, USA
How much does it cost to hire a Personal Assistant in Chicago through Lighthouse Careers?
Lighthouse Careers operates on a success-fee model, meaning there are no upfront costs to begin your search for a Personal Assistant in Chicago. You only pay our placement fee once we successfully match you with the right candidate and they accept your offer. This approach ensures we're fully invested in finding you the perfect Personal Assistant who meets your specific requirements. Our fee structure is transparent and competitive within the luxury staffing market, allowing you to focus on finding the ideal candidate without worrying about initial expenses.
What is the typical timeline to hire a Personal Assistant in Chicago?
Our streamlined process allows you to hire a Personal Assistant in Chicago within 1-2 weeks on average. We deliver your first shortlist of pre-vetted candidates within 24 hours of receiving your requirements. This rapid turnaround is possible due to our extensive network of qualified professionals and our efficient screening process. The exact timeline may vary depending on your specific requirements, schedule availability for interviews, and decision-making process, but our goal is always to connect you with exceptional candidates as quickly as possible.
What qualifications should I look for when hiring a Personal Assistant in Chicago?
When hiring a Personal Assistant in Chicago, look for candidates with relevant experience in high-net-worth households or executive support roles. Key qualifications include:
- Proven discretion and confidentiality handling
- Excellent organizational and time management skills
- Strong communication abilities
- Proficiency in technology and travel coordination
- Experience with luxury service standards
- Flexibility to adapt to changing schedules
Many top Personal Assistants in Chicago also have backgrounds in hospitality, corporate administration, or previous private household experience.
How does Lighthouse Careers vet Personal Assistant candidates in Chicago?
Our comprehensive vetting process for Personal Assistant candidates in Chicago includes thorough background checks, criminal history screening, and detailed reference verification from previous employers. We conduct in-depth interviews to assess both technical skills and cultural fit for your household. Our evaluation covers communication style, problem-solving abilities, discretion levels, and experience with luxury lifestyle management. We also verify credentials, assess technology proficiency, and evaluate their understanding of high-net-worth client expectations. Only candidates who pass our rigorous screening process are presented to our clients.
Does Lighthouse Careers offer a replacement guarantee for Personal Assistant placements in Chicago?
Yes, we stand behind our Personal Assistant placements in Chicago with a comprehensive replacement guarantee. If your placed Personal Assistant doesn't work out within the guarantee period, we will conduct a new search at no additional cost to you. This guarantee reflects our confidence in our vetting process and our commitment to ensuring you find the right long-term match. The specific terms and duration of our replacement guarantee will be detailed in your service agreement, providing you with peace of mind in your hiring decision.
Are there any specific advantages to hiring a Personal Assistant in Chicago versus other cities?
Chicago offers unique advantages for Personal Assistant hiring, including a large pool of experienced professionals from the city's robust corporate and hospitality sectors. The city's central location makes it ideal for Personal Assistants who coordinate travel across the country. Chicago's cost of living is generally lower than coastal cities like New York or San Francisco, potentially offering better value in salary negotiations. The city's strong transportation infrastructure, including O'Hare and Midway airports, makes it convenient for Personal Assistants managing complex travel itineraries. Additionally, Chicago's cultural richness provides Personal Assistants with extensive experience in luxury lifestyle management.
What services are included when I work with Lighthouse Careers to hire a Personal Assistant?
Our comprehensive service includes initial consultation to understand your specific needs, candidate sourcing from our extensive network, complete vetting and background screening, interview coordination, and reference checking. We also provide salary benchmarking guidance, contract negotiation support, and onboarding assistance. Throughout the process, you'll have dedicated support from our experienced consultants who understand the unique requirements of ultra-high-net-worth families. Our service extends beyond placement with ongoing support to ensure a successful long-term employment relationship with your new Personal Assistant.
How do I get started with hiring a Personal Assistant in Chicago through Lighthouse Careers?
Getting started is simple and straightforward. Contact us for an initial consultation where we'll discuss your specific Personal Assistant needs, household requirements, and expectations. We'll gather details about your lifestyle, schedule, and any specialized skills needed. Within 24 hours of this consultation, you'll receive your first shortlist of qualified Personal Assistant candidates in Chicago. There are no upfront fees, and our team will guide you through each step of the hiring process, from initial interviews through final selection and onboarding of your new Personal Assistant.
What salary should I expect to pay a Personal Assistant in Chicago?
Personal Assistant salaries in Chicago typically range from $60,000 to $120,000+ annually, depending on experience level, specific responsibilities, and household complexity. Entry-level positions may start around $50,000-$65,000, while experienced Personal Assistants with luxury household backgrounds can command $80,000-$120,000 or more. Factors affecting compensation include travel requirements, hours of availability, additional skills like event planning or property management, and the level of responsibility. We provide detailed market analysis and salary benchmarking to help you offer competitive compensation that attracts top-tier Personal Assistant talent in Chicago.
Do Personal Assistants in Chicago typically work live-in or live-out arrangements?
Most Personal Assistant positions in Chicago are live-out arrangements, allowing candidates to maintain their own residences while providing dedicated professional support. Live-out arrangements are preferred by many professionals in Chicago's robust job market and offer flexibility for both employer and employee. However, some ultra-high-net-worth families do require live-in Personal Assistants, particularly for estates outside the city center or when extensive travel coordination is required. We can accommodate both preferences and will clearly communicate arrangement expectations to candidates during our search process.
Are Personal Assistants in Chicago expected to travel with employers?
Travel requirements vary significantly depending on your lifestyle and business needs. Many Personal Assistants in Chicago are expected to coordinate complex travel arrangements but may not always accompany employers on trips. Some positions do require domestic or international travel, particularly for families with multiple residences or extensive business travel. We clearly outline travel expectations during our search process, including frequency, destinations, and duration. Personal Assistants with travel experience often command higher salaries, and we ensure candidates understand and are comfortable with your specific travel requirements before presenting them for consideration.
How do trial periods and contracts work for Personal Assistant positions in Chicago?
We recommend implementing a trial period, typically 30-90 days, when you hire a Personal Assistant in Chicago. This allows both parties to ensure compatibility and role fit before committing to long-term employment. We assist with employment contract development, including terms of employment, confidentiality agreements, job responsibilities, and termination clauses. Contracts should address compensation, benefits, work schedule, travel expectations, and household policies. Our team provides guidance on industry-standard contract terms and can recommend employment attorneys familiar with private household staffing if needed. Clear contractual agreements protect both employer and employee interests.
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Our Placement Guarantee
We're so confident in our matching process that we offer a replacement guarantee. If your placed Personal Assistant doesn't meet expectations within the guarantee period, we'll find a replacement at no additional cost.

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