Award-Winning Steak House | Classic Surf 'n' Turf | Live Entertainment | Californian Wines | Supper-Club Decor
When to Go: Try to plan your dinner for a Friday night around 8 p.m. That’s when musicians hit the adjoining Alley Cat Lounge stage, playing everything from oldies and jazz to modern rock and R&B.
Inside Tip: Show up hungry. All meals come with a salad, relish tray, and sourdough bread with butter and honey. A side of butter-sauteéd mushrooms also accompanies every steak.
Media Mentions: Over the years, 5 O’Clock has drawn national attention. The Travel Channel featured it on the program Steak Paradise, Saveur magazine named it one of the best steak houses in the country, and Travel + Leisure said it has a "Mad Men vibe."
Behind the Name: According to the restaurant's lore, the steak house got its name from an alarm clock that would ring every day at 5 p.m., alerting customers that it was time for a free drink.
While You’re in the Neighborhood
Before: Tour the Tripoli Shrine Center (3000 W. Wisconsin Avenue), a replica of the Taj Mahal and a member of the National Register of Historic Places.
After: If the entertainment at the Alley Cat Lounge isn't to your taste, head over to The Coffee House (631 N. 19th Street), which offers acoustic music and poetry performances.
Milwaukee ChopHouse's menu of succulent fare begins with ahi tuna tartare with avocado, wasabi, and sriracha ($12) and wagyu beef carpaccio in a white truffle oil with parmigiano reggiano and capers ($13)—both of which sharpen the palate for the main event: the ChopHouse's signature boneless 16-ounce strip steaks prepared au poivre ($35), crab Oscar-style ($42), blue-cheese crusted ($39), or with truffle butter ($39). The kitchen also turns out hot non-bovine entrees such as sautéed sea bass with sundried tomato and basil pesto ($32) and lobster tail ($51), a.k.a. mermaid steak.