Chicago has many names—The Windy City, Second City, City of the Big Shoulders—but as someone who was born and raised in this Midwest crossroads, I call it The Biggest Little City. Chicago might be the third biggest metropolis in the U.S., but it’s a honeycomb of distinct pockets—from the West Loop, which smashes trendy restaurants in brick warehouses next to old-school butchers, to the artful vibes of Pilsen, where boutiques and galleries intermingle with bodegas and panaderias—there’s so much substance beyond downtown’s Magnificent Mile, and yeah, The Bean. In fact, if you only stay downtown, you’re doing yourself a disservice.
This is one of those cities in which the history and culture are inescapable even on a simple stroll. From every block of its namesake brick to hearing Kanye West as you pull up at a neighborhood bar to a random encounter with Chance the Rapper outside a record store, Chicago is a distinctly tangible experience—a massive city disguised as a bustling neighborhood.
The next time you roll through, though it’s perfectly acceptable to dip your toes into The Loop, skip Navy Pier. You can do so much better. Venture to some of our picks below and get to know Chicago through the breadth of its people, legendary bites, and eclectic nights out. Oh, and if you want to grab a Chicago hot dog? No ketchup. And buy it at Home Depot for $3 with a bag of chips. Trust us.