Private Principal in Chicago’s North Shore Suburbs Seeking a Full-Time, Live-In Housekeeper 

Position: Full-Time, Live-In Housekeeper / Cook / 

Location: Chicago’s North Shore Suburbs, Illinois & Palm Beach, Florida 

Schedule: 5 days per week, approximately 8:30 a.m.–5:00 p.m., with two non-consecutive days off. Some flexibility is required based on the Principal’s needs, and the schedule is somewhat negotiable. 

Salary: $75,000–$95,000 annually, depending on experience 

Start Date: ASAP, ideally by early November 

Relocation: Local candidates preferred; open to candidates willing to relocate to the Chicago area 

Benefits: Health insurance stipend, two weeks of paid time off, discretionary bonuses throughout the year, and meals during working days are provided.

About the Principal

A private household in Chicago’s North Shore suburbs is seeking a dedicated, caring, and service-oriented Housekeeper / Cook to support an active elderly woman who divides her time between Illinois and Palm Beach, Florida.

The Principal resides in a large home in Illinois, although many areas of the residence are rarely used and do not require regular attention. She typically spends approximately six months of the year in her Palm Beach apartment, beginning in November.

The ideal candidate will be comfortable transitioning between both residences and providing a combination of housekeeping, simple meal preparation, transportation, and thoughtful personal assistance.

This position is best suited for someone who genuinely enjoys caring for others, takes pride in providing exceptional service, and understands the importance of making the Principal feel comfortable, supported, and well cared for.

Responsibilities

Housekeeping & Household Management

• Maintain a clean, organized, and welcoming home, with particular attention to the Principal’s regularly used living spaces.

• Perform general housekeeping duties, including laundry, changing linens, tidying, and maintaining household organization.

• Adjust housekeeping routines to accommodate the larger Illinois residence and smaller Palm Beach apartment.

• Work collaboratively and respectfully with building personnel and other household staff, particularly while in Palm Beach.

• Assist with household errands and miscellaneous personal or family-related tasks as needed.

Cooking & Meal Preparation

• Prepare simple, fresh, and healthy meals according to the Principal’s preferences and dietary requirements.

• Follow recipes confidently and accommodate the Principal’s low-FODMAP diet.

• Be comfortable preparing basic chicken dishes, fish, tuna, salads, and other straightforward meals.

• Assist with grocery shopping, meal planning, and maintaining an organized kitchen.

• Adapt to the Principal’s dining preferences, recognizing that she frequently enjoys meals at restaurants and her country club, particularly while in Palm Beach.

Transportation

• Provide reliable, calm, and safe transportation to medical appointments, social engagements, errands, and other activities.

• Assist with medication organization and reminders, paying close attention to the Principal’s established medication schedule and instructions.

• Offer thoughtful assistance with daily routines while respecting the Principal’s independence and preferences.

• Anticipate needs and provide attentive, personalized service without being intrusive.

• Accompany the Principal during her seasonal stay in Palm Beach and assist with travel-related household arrangements.

• Provide occasional family assistant support and additional personal assistance as needed, particularly while in Florida.

Ideal Candidate & Personality

The ideal candidate is naturally caring, patient, calm, and highly service-oriented, with a genuine desire to make the Principal’s daily life easier and more enjoyable.

A strong hospitality mindset and a willingness to assist wherever needed are essential. The Principal is seeking someone who understands the importance of attentive, personalized service and takes satisfaction in ensuring that her needs are met.

The candidate should be an especially calm, confident, and patient driver who remains composed when receiving directions or feedback from the Principal.

A warm, reassuring presence, excellent judgment, and the ability to maintain a peaceful environment are particularly important. The successful candidate will be adaptable, discreet, dependable, and comfortable working both independently and collaboratively with other staff.

This is an excellent opportunity for a dedicated household professional who enjoys building a meaningful, long-term working relationship with one Principal.

Requirements

• Previous experience in a private household, ideally in a combined housekeeping, cooking, or personal assistant role.

• Strong housekeeping and household organizational skills.

• Comfortable preparing simple, healthy meals and following recipes, including those accommodating dietary restrictions.

• Ability to speak, read, and understand English fluently.

• Valid driver’s license and clean driving record.

• Calm, confident driving skills and willingness to transport the Principal regularly.

• Excellent professional references and ability to pass a background check.

• Comfortable assisting with medication organization and reminders according to established instructions.

• Willingness and ability to spend approximately six months annually in Palm Beach, Florida.

• Ability to work respectfully and effectively with building staff and other household personnel.

• Flexibility with scheduling and responsibilities based on the Principal’s needs.

• Legally authorized to work in the United States.

• Candidates currently residing near Chicago’s North Shore suburbs are preferred, although relocation candidates will be considered.

Additional Details

The position includes private accommodations in the Principal’s Palm Beach apartment during the seasonal stay, with meals provided on working days. All work-related travel expenses between Illinois and Florida will be covered.

The Principal is looking to hire as soon as possible, ideally securing the right candidate by the beginning of November.

The priority is finding a kind, patient, dependable professional who can balance excellent housekeeping and basic cooking skills with genuine attentiveness, flexibility, and a strong commitment to personal service.