How to Build a Reliable Winter Hotel Staff Plan (When the Weather and Flu Won’t Cooperate)

Winter in the Midwest is more than just a season. It can feel like an obstacle course. For hotel managers in cities like Chicago, the challenge is keeping up a luxury guest experience while staff numbers drop due to flu, winter storms, and heavy snow.

When the wind chill drops and you start getting 'I can’t make it' texts, the key to avoiding service problems is having a proactive staffing plan. Here’s how to prepare by staffing for the 2026 season.

The “Midwest Double-Whammy”

In a city like Chicago, winter occupancy doesn’t always slow down; it just changes. Corporate annual meetings, indoor conventions, restaurant week, Valentine’s Day, and stranded travelers keep demand for great service high. Unfortunately, this happens right when flu season is at its worst.

According to a recent report from Rush University Medical Center, “Chicago and the U.S. rang in the new year with a flurry of flu cases, setting 2025-26 on pace to be one of the busiest influenza seasons in years.”

For hotel managers, this means your staff is not just dealing with traffic, but also with the pressure of flu season. Relying on a small team during these months is no longer just about saving money; it puts your service at risk.

The High Cost of Powering Through With Sick Hotel Staff

It can be tempting to ask an employee who is a little sick to work their shift anyway. But in hospitality, this is risky. One sick server in a busy banquet hall can lead to many more staff getting sick by the next weekend.

Fisher Phillips, in their 2026 Flu Season Advisory, notes: “A strong sick-leave framework reduces avoidable transmission, supports employees who do the right thing by staying home, and helps you maintain continuity.”

Besides illness, keeping your staff safe is just as important. If a blizzard hits, asking a housekeeper to travel from the suburbs can cause accidents or lead to burnout. A good plan finds out which staff live close by or along main plowed roads, so your essential team can actually get to work.

Don’t let a snowstorm or flu outbreak hurt your revenue. By building a staffing safety net with WD Hospitality Staffing, you can make sure your doors stay open and your guests stay happy, no matter what the Chicago weather brings.

By the Numbers: The 2026 Labor Landscape

There is less room for error than ever. The American Hotel & Lodging Association (AHLA) says the hospitality industry will face an 18% labor shortage in 2026. This shortage is worst in front-of-house and housekeeping jobs, which are the most likely to have winter call-outs.

If you lose 18% of your staff to a national shortage and another 15% to the flu, you are now working with almost 35% fewer people. This is when having a strategic partner is most valuable.

Building the Flexible Hotel Staff Bench

To survive the winter, hotel managers must pivot from reactive scrambling to a flexible staffing model.

1. Cross-Training for Agility: Ensure your bell staff can assist with basic food and beverage service, and train your concierge team to support the front desk during busy check-in periods, such as flight cancellations.

2. Incentivize the Early Arrival: In their Midwest Workforce Guideline, Cardinal Staffing that managers should, “Offer flexible scheduling options… Stagger start times to allow for safer commutes during peak traffic or snowfall.”

3. Use WD Hospitality Staffing as your insurance policy. Instead of spending three hours on the phone trying to fill a vacancy, one call to us scales your team instantly with pre-vetted, professional hotel staff. Get all the contact details you need here: https://www.wdhstaff.com/contact

   
   

Reliability is a Reputation-Builder

With instant online reviews, guests don’t usually accept 'the weather' as an excuse. They expect hot coffee, clean rooms, and a staffed front desk. Your staffing plan demonstrates your brand's commitment to great service.

Use WD Hospitality Staffing!

When a blizzard or a flu outbreak hits your housekeeping department, you don't want help from a national call center; you need a local partner who understands the grit of a Chicago winter.

Here is why WD Hospitality Staffing should be your first call:

• 30 Years of Midwest Expertise: We’ve been with you for three decades of Chicago winters. We know the seasons of our city, and we have the database of trained staff to keep your service standards high without missing a beat.

• Deep Local Knowledge: Our hotel staff are locals who know the transit routes and the traffic problems. We don't just send bodies; we send professionals who can reach your property when it matters most.

• 24/7 Local Support: Emergencies don't happen Monday through Friday between 9 and 5pm. Whether it's a 4:00 AM call-out or a midnight pipe burst, you have access to a real and local person via our 24/7 hotline.

Don't leave your reputation to chance. Request a quote and secure your backup team today: Request a Quote By Clicking Here.

References

American Hotel & Lodging Association. (2025). 2026 State of the hotel industry: Addressing the national labor shortfall. https://www.ahla.com/research/state-of-the-industry-2026

Cardinal Staffing Services. (2025, October 12). Midwest workforce guidelines: Managing seasonal absenteeism in logistics and hospitality. https://www.cardinalstaffing.com/tips-for-managing-absenteeism/

Fisher Phillips. (2025, November 4). Hospitality employer’s guide to the 2026 flu and respiratory season. https://www.fisherphillips.com/en/news-insights/this-flu-season-will-get-worse-before-it-gets-better.html

Rush University Medical Center. (2026, January 15). Chicago health watch: Tracking the 2025-26 influenza peak. https://www.rush.edu/news/2025-26-flu-season-hits-hard