Sure, there are the classics like Brit artist Anish Kapoor’s Cloud Gate sculpture (aka ‘The Bean’) in Millennium Park, catching a Cubs game at Wrigley Field, or scoring a slice of deep-dish pizza at places like Pequod's, The Art of Pizza or Lou Malnati’s.
But you can also stumble upon new spots every time you’re in town, like one of the many small businesses that call the city home. Kick off your day at Back of the Yards Coffee on the South Side; or grab some reading material at Semicolon Bookstore before walking over to the city's eponymous river to flick through it with a view.
And while you can always experience the city’s famed comedy scene at theaters like The Second City, rotating casts of future stars performing improv ensure that you’ll never see the same show twice. Similarly, no two visits to this iconic metropolis will ever be the same either.