Fittingly dubbed the Windy City, the landscape of Chicago seems to change with the breeze, with new restaurants, shops, and attractions to discover every time you visit.

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 shop at Semicolon Bookstore before walking over to the city's eponymous river to read with a view. And while you can always experience the city’s famed comedy scene at theaters like the iO, 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.

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