Presidio sundae at Ghirardelli
The size and price ($10) suggest sharing—and I did—but it was a struggle. Ghirardelli Ice Cream & Chocolate Shop, 830 N. Michigan Ave. 312-337-9330
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Best Butcher Shop
They don’t make them like Gepperth’s anymore, which is a shame, because the tiny 109-year-old store may offer the perfect meat-shopping experience. You’ll find protein galore, from housemade Sheboygan-style bratwursts to vacuum-sealed elk patties, all of impeccable quality. Longtime owner Otto Demke (above) will slice your order himself.
Best Rooftop Boozing
Both Zagat’s and Michelin’s 2013 and 2014 Chicago guides recommend bartender Rico Salinas’s bright cocktails, such as the Effen Avocado, made with cucumber vodka and avocado, and a punched-up margarita mixed with cranberry purée. Seats fill up fast, but there’s plenty of standing room and lots of skyline to gaze upon. Get bottle service at … Read more
Best Teashop
For the highest quality and widest selection (250 loose-leaf teas from around the world, including exotics such as Malawi Satemwa Zomba Pearls), head to these outposts—the only two in the country—of the posh German chain (pronounced tee-SCHWEN-dnar). Prices range from $8.50 to $80 (!) for 100 grams—but you can get a free sample if you … Read more
Best Caterer
Whether Wendy Pashman is working a dinner for 10 (starting at $1,000) or a wedding for 400 (from $52,000), she overlooks no detail. She can match the cuisine to your china and crystal. (Got hand-painted dishes from Provence? Then foie gras it is.) And if you want the servers to be as beautiful as the … Read more
Best Mixology Class
Get some history with your hooch at this swanky bar’s hyperniche mixo classes, which pair technical knowhow with cocktail lore. Casual drinkers should opt for the one-session master class—which runs five times a year and tracks the evolution of the cocktail (costs vary; the most recent was $150)—but enthusiasts can arrange private crash courses. What’s … Read more