The city's most extraordinary neighborhood is a hive of activity until 5 p.m.—and that's when the action really starts.
The Loop is Chicago’s most famous ’hood—and possibly its most under-appreciated. Too many tourists, they say. It’s a no-man’s-land at night, they say. But in the past few years, all that has changed. From white-hot dining and drinking destinations to a theater district that’s never been more bustling, this historic district south of the Chicago River now more than ever truly comes to life when the suits go home. Here’s the scoop on this fast-transforming hub.
WHERE THE ACTION IS: State and Madison Streets is Loop ground zero, with prime attractions (from Millennium Park to the theater district) all within a few blocks in any direction.
THE CROWD: Corporate types cutting loose after work at new Gray Hotel hot spot Boleo; Instagrammers snapping street art pics; foodies exploring haute food courts Revival Food Hall and Latinicity.
WHEELS: Divvy bikes for jaunts along the lake and across the river to Fulton Market District.
CRAVING: Poutine with cider-braised pork shoulder at The Gage.
GREEN MEANS: Picnics on the Pritzker Pavilion lawn at Millennium Park.
HANDBAG OF CHOICE: Valentino Rockstud Rolling Messenger bag ($3,645), which can transition from client meetings to cocktails on the rooftop at LondonHouse with ease.
SIGNATURE TIPPLE: The Grey Garden, at Cindy’s Rooftop: Tito’s vodka, Dolin Blanc vermouth, crème de violette, Emperor’s Jasmine Pearl tea, and lemon.
RETAIL THERAPY: Luxe custom-made men’s hats by milliner extraordinaire Graham Thompson at Optimo.
BABY NAMES: Pick a street, any street: Monroe, Jackson, Harrison, Roosevelt...