Winter in Chicago isn’t just cold – it’s expensive. And if you employ household staff, you’re about to discover costs you never factored into your budget when you hired people. Snow removal, transportation delays, heating bills that triple, extra cleaning from salt and slush tracked through your house, and the reality that some tasks just can’t happen when it’s 10 degrees outside with a windchill making it feel like negative 20.
At Seaside Staffing Company, we work with Chicago families every winter who are shocked by how much the season affects their household operations and budget. The salary you pay your estate manager stays the same year-round, but the actual cost of running your household with staff goes up significantly from November through March. Understanding what those costs are helps you budget properly and set realistic expectations with your staff about what’s possible during Chicago’s brutal winter months.
Transportation is the first cost that hits you. When there’s a major snowstorm, your housekeeper who normally has a 30-minute commute might be looking at two hours each way, if they can get to you at all. Some families pay for ride services when weather is bad so staff don’t have to navigate their own cars through dangerous conditions. Others increase mileage reimbursement during winter months to cover the wear and tear on vehicles from salt, potholes, and rough conditions. If your staff takes public transport, expect delays and cancellations that mean they’re arriving late or not at all on the worst weather days.
Smart families build snow day protocols into their employment agreements. What happens when the city is shut down and your housekeeper can’t safely get to your house? Are they still paid? Do they use PTO? Can they make up hours later? If you don’t establish this upfront, you’re going to have awkward conversations every time there’s a major storm. At Seaside Staffing Company, we recommend families guarantee a certain number of paid snow days per winter so staff aren’t financially penalized for weather beyond their control, while also setting expectations that staff make reasonable efforts to get to work when conditions allow.
Snow removal becomes a massive issue if you have property beyond just a small city lot. Your estate manager or house manager is suddenly coordinating with snow removal services, managing when driveways and walkways get cleared, dealing with ice melt supplies, and making sure your property is accessible and safe. If snow removal wasn’t explicitly part of their job description, you’re looking at either adding it to their responsibilities or hiring seasonal help. Either way, it’s a cost you didn’t have in summer.
Heating costs spike dramatically, and if your household staff are responsible for managing utilities and vendors, they’re dealing with HVAC service calls, emergency repairs when systems fail during cold snaps, and monitoring to make sure pipes don’t freeze. Your house manager might need to coordinate with heating contractors, schedule maintenance, and handle issues that only come up in winter. This takes time and energy that in warmer months would be directed toward other household projects.
The amount of cleaning required increases substantially. Every time someone enters your house, they’re tracking in salt, snow, slush, and mud. Your housekeeper is doing extra floor cleaning, extra mopping, extra vacuuming, dealing with salt stains on floors and carpets, and managing the sheer volume of wet outerwear that needs to be dealt with. Entry areas take a beating all winter and require constant attention. What used to be a weekly deep clean of your foyer is now happening multiple times per week just to keep it presentable.
If you have household staff who handle outdoor tasks – maintaining your yard, managing outdoor furniture and equipment, handling exterior maintenance – those responsibilities don’t disappear in winter, they just change. Now your staff are coordinating storm prep, dealing with winter damage to property, managing snow accumulation on structures, and handling issues like ice dams or frozen pipes. For staff who came from warmer climates or who’ve never managed a Chicago winter property, there’s a learning curve that costs you time and potentially money when things go wrong.
Seasonal supplies and equipment become necessary expenses. Ice melt, snow shovels, extra door mats, boot trays, weatherstripping, emergency supplies in case of power outages. Your house manager needs to anticipate these needs, purchase supplies before they’re needed, and manage inventory throughout the winter. Some families are surprised to discover how much they’re spending on winter-specific household supplies they never needed in other seasons.
Indoor projects pile up because outdoor work becomes impossible for months. Your estate manager who was handling landscaping vendors and exterior maintenance all summer is now trying to fill their time with indoor tasks. This can actually be valuable – winter is when you tackle those indoor projects you’ve been putting off – but it requires planning and coordination. If you don’t have a winter project list ready, you’ve got staff who are underutilized or trying to manufacture tasks to fill their time.
At Seaside Staffing Company, we encourage families to have explicit conversations with household staff before winter hits about what changes and what’s expected. Does your house manager have the authority to hire snow removal services without checking with you first? What’s the budget for winter maintenance and supplies? What tasks are lower priority in winter versus summer? Having these conversations in October prevents conflicts and confusion in January.
The mental and physical toll of winter shouldn’t be underestimated either. Staff who are commuting in terrible conditions, working in a season where everything takes longer and is harder, and dealing with the general misery of Chicago winter need extra support and patience. Your housekeeper isn’t being lazy when it takes them longer to complete normal tasks – they’re managing wet floors, extra cleaning, and the physical exhaustion of working through a brutal season.
Some families offer winter bonuses or hazard pay for staff who maintain reliable attendance through the worst months. Others provide flexibility around start times during bad weather – your estate manager can come in an hour late when roads are terrible without it being a problem. Building in this flexibility recognizes the reality that winter creates challenges that aren’t present the rest of the year.
Consider whether you need additional seasonal help. Some families hire extra housekeeping support just for winter months to handle the increased cleaning load. Others bring in specialized contractors for snow removal and winter maintenance so their regular staff can focus on their normal responsibilities. This is especially important if you have staff who aren’t physically equipped to handle heavy snow shoveling or who have health issues that make working in extreme cold difficult.
Utilities are another cost that spikes. Your heating bill is higher, you’re using more hot water, you might be running humidifiers to combat dry air, and everything related to keeping your house warm and livable goes up. If your house manager is responsible for paying bills and managing budgets, they need to know that winter utility costs are expected to be significantly higher and that’s not something they’re being judged on.
The flip side is that some expenses decrease. You’re not watering your lawn, you’re not running your pool equipment, you’re not maintaining outdoor entertaining spaces, and your cooling costs are zero. Smart household budgets account for seasonal fluctuation rather than expecting consistent costs year-round. Your estate manager should be tracking these patterns and helping you understand the actual cost rhythm of running a Chicago household.
Transportation options change too. If you employ drivers or if driving is part of any household staff role, winter requires different skills and different vehicles. A car that’s fine for summer driving might be inadequate for winter conditions. Some families provide winter vehicles or pay for winter tires and equipment for staff who drive as part of their jobs. This is a cost that prevents bigger problems down the line when your staff can’t safely transport your children or complete errands because they’re driving inappropriate vehicles for the conditions.
Emergency preparedness becomes essential. Your household staff need to know what to do if power goes out, if heating fails, if pipes freeze, if the city is shut down for multiple days. Having emergency supplies, backup plans, and clear protocols costs money upfront but saves you from disaster expenses later. Your estate manager should be driving this planning, but they need budget and authority to make it happen.
At Seaside Staffing Company, we tell Chicago families to budget roughly 20-30% more for household operations during the four worst winter months compared to their summer baseline. That accounts for increased cleaning, higher utilities, transportation challenges, snow removal, seasonal supplies, and the general inefficiency that comes with everything being harder in winter. Families who budget for this aren’t surprised by the costs. Families who don’t budget for it end up frustrated and looking for places to cut expenses that usually end up being unfair to staff.
Winter also affects hiring and retention. The best household staff in Chicago factor winter working conditions into their employment decisions. A position that requires a brutal commute through winter weather is less attractive than one with easier access or flexibility around weather. Families who understand this and accommodate it accordingly have an easier time attracting and keeping good people.
The bottom line is that winter isn’t just a season in Chicago – it’s a significant operational challenge that affects every aspect of household management and creates real costs beyond what you’re paying in salary. Plan for it, budget for it, communicate about it with your staff, and accept that running a household through a Chicago winter costs more than running it through summer. That’s not a problem to solve, it’s just reality to acknowledge and prepare for.
