Milwaukee's busiest office space sits in a few pockets. CBRE put metro vacancy at 18.4% in the third quarter of 2026, but the Third Ward and Walker's Point were at 11.0%, while Mayfair and Wauwatosa ran 25.4% and Brookfield 19.9%. Downtown East absorbed 60,000 square feet that quarter, and Northwestern Mutual is moving nearly 2,000 people from Franklin into its rebuilt downtown North Office Building ahead of a 2027 opening. In Wauwatosa, the Milwaukee Regional Medical Center campus has more than 16,000 employees. On the caterer side, Apple Spice delivers to the Third Ward and East Side from Menomonee Falls, Milwaukee Street Catering covers Wauwatosa, Brookfield, Whitefish Bay, Shorewood and Mequon, and Skyline and Charlie's both run weekday office delivery out of South Milwaukee.
Only four of these caterers publish prices. Skyline lists box lunches at $8.95 to $12.95 with no weekday minimum. Charlie's lists box lunches at $10.54 per person and delivers to groups of 10 or more. Sendik's boxed lunches run $10.99 to $12.99 with a 10 lunch minimum and 48 hours' notice, which goes to 72 hours over 50 lunches and five days over 100. Zilli Hospitality Group says drop-off starts around $30 per guest and staffed events around $50. Tall Guy and a Grill doesn't post per-person prices but sets a $1,500 minimum for drop-off. If you'd rather not call anyone, Sendik's, Skyline, Apple Spice and Cafe Corazon's Brown Deer location take orders online. Saz's, Emerald City, Speed Queen and Milwaukee Street Catering quote each event through a form.
A few Milwaukee specifics before you order. Inside the city, sales tax is 7.9%, made up of the 5% state rate, 0.9% for the county and a 2% city tax that started in 2024, and Wisconsin taxes a delivery charge on a taxable sale too. Fees vary a lot. Charlie's starts delivery at $15 and adds an automatic 5% gratuity after 3:30pm and on Saturdays, Sendik's charges $25 to deliver boxed lunches, Skyline's evening delivery is $30 or more, and Tall Guy and a Grill charges from $55 for delivery and setup. Chef Jack's, Irene's and Antigua lean toward full-service events and quote everything. And when the Baird Center, now 1.3 million square feet after a $456 million expansion, has a big convention in town, book earlier than usual.