With its flourishing food and drink scene, there’s never been a better time to drop into Chicago for a cocktail-centric jaunt. Here’s your guide to an elevated bar crawl through the Windy City, with some necessary sustenance along the way to keep your food-to-alcohol ratio on point.
Friday afternoon: Upon arrival in Chicago, make your way to The Publishing House Bed and Breakfast in the West Loop. On the top floor, you’ll find a café where you where you can order a French press, offering the perfect buzz for your long night of dining and drinking ahead (hitting up Solo Salon next door for a pre-going-out blowout or pedicure is optional).
Caption: Bedroom at the Publishing House
Friday evening: Head downstairs to The Press Room, a subterranean wine and cocktail bar with an approachable menu of elevated American fare. After a round or two (plus a cheese board or two), hop in a cab and head across the river for a two-part, tiki-themed mini crawl; Three Dots and a Dash is among the city’s best bars, and a pioneer of the country’s modern tiki revival. Just be sure to save room for Lost Lake afterward, an equally excellent tiki bar with a slightly more glam aesthetic.
Saturday afternoon: Roll out of bed for a leisurely cocktail-fueled brunch at Beatnik, a bohemian West Town masterpiece. Don’t miss out on the “Walk ‘O’ Sin” cocktail (rum, Calvados, Oloroso sherry, chai cinnamon bun orgeat, orange, lemon, black walnut) or the duck egg shakshuka.
Should you feel like walking off this plentiful meal, the Fulton Market area is a 30-minute walk from Beatnik. It’s an excellent place to explore, and best of all, it’s on the way back to the hotel. Make sure to stop by Fulton Market Kitchen, even if just for a peek at its visually stunning interior.
Saturday night: After freshening up at the hotel, grab a cab and head to Logan Square for a pre-dinner cocktail at The Pink Squirrel, a retro-chic bowling alley celebrating often overlooked Midwestern classics like Brandy Alexanders and Grasshoppers. For dinner, make your way to an evening of Spanish fare at Black Bull, where Chicago’s largest sherry menu will carry you through each course. And because no dinner is complete without a nightcap, make the trek upstairs to Bordel, where cabaret-style entertainment and modern spins on Prohibition-era cocktails (see: The Stranger Things, made with vodka, sherry, grape and ylang-ylang) await.
Sunday morning: Wake up early to spend as much quality time with The Publishing House’s renowned breakfast spread as possible. From there, pack up, check out, and venture back to wherever you call home.