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

Best Cooking Class

Somewhere between a one-off class at a community center and a year of culinary school lies this brass-tacks boot camp, which teaches professional techniques to home cooks in just five sessions ($1,750, including food). You’ll come away with new mastery of the key skills—seasoning, knife tricks, plating—which you’ll use nearly every time you whip up … Read more

Best Wine Shop

While Andersonville’s In Fine Spirits provides serious competition, this smallish Old Town institution prevails, thanks to its passionate, personal service (five generations of Glunzes have curated the selection) and long-standing relationships with vintners from France to Lebanon. Uncork a summertime rosé—perhaps the 2014 Domaine de Triennes ($17), a cult favorite—on the pleasant sidewalk patio.