A thin line separates timeless from tired, and this Gold Coast institution never crosses it. The servers wear white jackets, give caramel-voiced spiels they’ve been honing for nearly four decades, and deliver cocktails (huge) and bread baskets (also huge) with alacrity. I feel so instantly cared for that I want the same steak dinner my grandfather (who never once heard the word “wagyu”) reveled in: a wedge salad, a twice-baked potato, and a black-and-blue slab of prime Angus. My pick: W.R.’s Chicago Cut, a bone-in rib eye named for the late Chicago Tribune columnist William Rice. Sometimes I skip the beef altogether and make a meal of garbage salad (chopped everything), shrimp cocktail, or the lumpiest of lump crab cakes. I have to confess I’ve never once set foot in the dining room. The bar, with its lubricated regulars and piano player, is my happy place, and in warmer months the Rush Street patio feels like the city’s soul. 

Price: $$$$
Address: 1028 N. Rush St.
Website: gibsonssteakhouse.com